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616-44-4 Usage

Description

3-Methylthiophene is a clear, colorless to light yellow liquid that belongs to the thiophene family of heterocyclic compounds. It is a derivative of thiophene with a methyl group attached to the third carbon atom, which gives it unique chemical properties and potential applications in various industries.

Uses

Used in Conducting Polymer Research:
3-Methylthiophene is used as an electropolymerization monomer in conducting polymer research. Its unique properties make it a valuable component in the development of new materials with enhanced electrical conductivity.
Used in Chemical Synthesis:
3-Methylthiophene serves as a conducting polymer precursor, which is essential for the synthesis of various polymers with specific properties. These polymers can be used in a wide range of applications, from electronics to energy storage.
Used in Inhibiting Polymerization:
3-Methylthiophene acts as an inhibitor for the polymerization of trichloroethylene in a solvent used for the degreasing of iron and aluminum. This polymerization is catalyzed by the contact of the solvent with the metals, and the use of 3-methylthiophene helps control the process and prevent unwanted reactions.
Used in Coffee and Coffee Products:
3-Methylthiophene is found in coffee and coffee products, where it contributes to the unique aroma of roast coffee. As a maillard product, it is a result of the complex chemical reactions that occur during the roasting process, adding to the rich flavor and aroma profile of coffee.
Used in Copolymerization:
The copolymerization of 3-alkylthiophene and 3-methylthiophene is a promising approach to create polymers with both solution processible properties and high electrical conductivity. These polymers can be utilized in various applications, such as in the development of electronic devices and sensors.

Purification Methods

Dry it with Na2SO4, then distil it from sodium. [Beilstein 17 III/IV 277, 17/1 V 331.]

Check Digit Verification of cas no

The CAS Registry Mumber 616-44-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 6 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 616-44:
(5*6)+(4*1)+(3*6)+(2*4)+(1*4)=64
64 % 10 = 4
So 616-44-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H6S/c1-5-2-3-6-4-5/h2-4H,1H3

616-44-4 Well-known Company Product Price

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  • TCI America

  • (M0440)  3-Methylthiophene  >98.0%(GC)

  • 616-44-4

  • 25g

  • 228.00CNY

  • Detail
  • TCI America

  • (M0440)  3-Methylthiophene  >98.0%(GC)

  • 616-44-4

  • 500g

  • 1,200.00CNY

  • Detail
  • Alfa Aesar

  • (A13394)  3-Methylthiophene, 98+%   

  • 616-44-4

  • 25g

  • 428.0CNY

  • Detail
  • Alfa Aesar

  • (A13394)  3-Methylthiophene, 98+%   

  • 616-44-4

  • 100g

  • 1251.0CNY

  • Detail
  • Alfa Aesar

  • (A13394)  3-Methylthiophene, 98+%   

  • 616-44-4

  • 500g

  • 5625.0CNY

  • Detail
  • Aldrich

  • (M84402)  3-Methylthiophene  98%

  • 616-44-4

  • M84402-25G

  • 494.91CNY

  • Detail
  • Aldrich

  • (M84402)  3-Methylthiophene  98%

  • 616-44-4

  • M84402-100G

  • 1,347.84CNY

  • Detail

616-44-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Methylthiophene

1.2 Other means of identification

Product number -
Other names 3-methyl thiophene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:616-44-4 SDS

616-44-4Synthetic route

2,5-Dichloro-3-methylthiophene
17249-90-0

2,5-Dichloro-3-methylthiophene

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; potassium hydroxide In methanol at 80℃; under 60006 Torr; for 24h;95.33%
3-Bromothiophene
872-31-1

3-Bromothiophene

bis(μ-[2-(dimethylamino)ethanolato-N,O:O]tetramethyldiindium

bis(μ-[2-(dimethylamino)ethanolato-N,O:O]tetramethyldiindium

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride In benzene at 80℃; for 24h;93%
3-thienyl iodide
10486-61-0

3-thienyl iodide

bis(iodozinc)methane
31729-70-1

bis(iodozinc)methane

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
Stage #1: 3-thienyl iodide; bis(iodozinc)methane With tris-(dibenzylideneacetone)dipalladium(0); tris<3,5-bis(trifluoromethyl)phenyl>phosphane In tetrahydrofuran at 40℃; for 0.5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water chemoselective reaction;
73%
3-hydroxymethyl-thiophene
71637-34-8

3-hydroxymethyl-thiophene

carbon monoxide
201230-82-2

carbon monoxide

A

thiophen-3-yl-acetic acid
6964-21-2

thiophen-3-yl-acetic acid

B

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;A 34%
B 11%
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h;A 34 % Spectr.
B 11 % Spectr.
thiophene
188290-36-0

thiophene

cis-Cp(*)W(CO)2(MeCN)(4-methyl-2-thienyl)

cis-Cp(*)W(CO)2(MeCN)(4-methyl-2-thienyl)

A

3-Methylthiophene
616-44-4

3-Methylthiophene

cis-Cp(*)W(CO)2(MeCN)(-2-thienyl)

cis-Cp(*)W(CO)2(MeCN)(-2-thienyl)

cis-Cp(*)W(CO)2(d3-MeCN)(-2-thienyl)

cis-Cp(*)W(CO)2(d3-MeCN)(-2-thienyl)

Conditions
ConditionsYield
A 32%
B 33%
C 6%
bis-(1-propenyl) sulfide
33922-80-4

bis-(1-propenyl) sulfide

A

thiophene
188290-36-0

thiophene

B

2-Methylthiophene
554-14-3

2-Methylthiophene

C

2-ethylthiophene
872-55-9

2-ethylthiophene

D

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
at 500 - 520℃; pyrolysis at atmospheric pressure in a nitrogen stream; Further byproducts given;A 32%
B n/a
C 25%
D n/a
Divinyl sulfone
77-77-0

Divinyl sulfone

A

thiophene
188290-36-0

thiophene

B

2-Methylthiophene
554-14-3

2-Methylthiophene

C

3-Methylthiophene
616-44-4

3-Methylthiophene

D

toluene
108-88-3

toluene

E

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

F

benzene
71-43-2

benzene

Conditions
ConditionsYield
With hydrogen sulfide at 580℃; thermal transformations of divinyl sulfone; further gaseous medium;A 12%
B 1.1%
C 3%
D 3.6%
E 0.4%
F 11%
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With aluminium oxide-chromium oxide; sulfur dioxide
i-Amyl alcohol
123-51-3

i-Amyl alcohol

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With aluminium oxide-chromium oxide; sulfur dioxide
methylbutane
78-78-4

methylbutane

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With aluminium oxide-chromium oxide; sulfur dioxide
3-Methyl-1-butene
563-45-1

3-Methyl-1-butene

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With aluminium oxide-chromium oxide; sulfur dioxide
isoprene
78-79-5

isoprene

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With sulfur at 350℃;
thiophene
188290-36-0

thiophene

dimethylfluoronium ion
64710-12-9

dimethylfluoronium ion

A

2-Methylthiophene
554-14-3

2-Methylthiophene

B

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With oxygen; trimethylamine In gas Product distribution; gas-phase methylation of furan and thiophene, pressure dependence, effect of partial pressure of NMe3, competition experiments in the presence of benzene; mechanism of methylation;
thiophene
188290-36-0

thiophene

dimethylchloronium
24400-15-5

dimethylchloronium

A

2-Methylthiophene
554-14-3

2-Methylthiophene

B

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With oxygen; trimethylamine In gas Product distribution; gas-phase methylation of furan and thiophene, pressure dependence, effect of partial pressure of NMe3, competition experiments in the presence of benzene; mechanism of methylation;
2-Methylthiophene
554-14-3

2-Methylthiophene

A

2-ethylthiophene
872-55-9

2-ethylthiophene

B

2,4-dimethylthiophene
638-00-6

2,4-dimethylthiophene

C

2,5-DIMETHYLTHIOPHENE
638-02-8

2,5-DIMETHYLTHIOPHENE

D

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;A 11.7 % Chromat.
B 0.6 % Chromat.
C 4.9 % Chromat.
D 9.2 % Chromat.
2,3-dimethylthiophene
632-16-6

2,3-dimethylthiophene

A

thiophene
188290-36-0

thiophene

B

2-ethylthiophene
872-55-9

2-ethylthiophene

C

2,5-DIMETHYLTHIOPHENE
638-02-8

2,5-DIMETHYLTHIOPHENE

D

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;A 3.1 % Chromat.
B 1.5 % Chromat.
C 1.0 % Chromat.
D 12.8 % Chromat.
2,3-dimethylthiophene
632-16-6

2,3-dimethylthiophene

A

2-Methylthiophene
554-14-3

2-Methylthiophene

B

3-Methylthiophene
616-44-4

3-Methylthiophene

C

toluene
108-88-3

toluene

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;A 6.6 % Chromat.
B 12.8 % Chromat.
C 4.1 % Chromat.
D 24.7 % Chromat.
2,3-dimethylthiophene
632-16-6

2,3-dimethylthiophene

A

3,4-dimethylthiophene
632-15-5

3,4-dimethylthiophene

B

2-ethylthiophene
872-55-9

2-ethylthiophene

C

2,4-dimethylthiophene
638-00-6

2,4-dimethylthiophene

D

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;A 2.3 % Chromat.
B 1.5 % Chromat.
C 1.5 % Chromat.
D 12.8 % Chromat.
3,4-dimethylthiophene
632-15-5

3,4-dimethylthiophene

A

2,3-dimethylthiophene
632-16-6

2,3-dimethylthiophene

B

2,4-dimethylthiophene
638-00-6

2,4-dimethylthiophene

C

2,5-DIMETHYLTHIOPHENE
638-02-8

2,5-DIMETHYLTHIOPHENE

D

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;A 5.1 % Chromat.
B 6.2 % Chromat.
C 1.1 % Chromat.
D 12.2 % Chromat.
3,4-dimethylthiophene
632-15-5

3,4-dimethylthiophene

A

2,4-dimethylthiophene
638-00-6

2,4-dimethylthiophene

B

2,5-DIMETHYLTHIOPHENE
638-02-8

2,5-DIMETHYLTHIOPHENE

C

3-Methylthiophene
616-44-4

3-Methylthiophene

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;A 6.2 % Chromat.
B 1.1 % Chromat.
C 12.2 % Chromat.
D 17.6 % Chromat.
3-Bromothiophene
872-31-1

3-Bromothiophene

methyl iodide
74-88-4

methyl iodide

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With n-butyllithium 1.) hexane, THF, -78 deg C, 1 h; 2.) -78 deg C to RT; Yield given. Multistep reaction;
2,4-dimethylthiophene
638-00-6

2,4-dimethylthiophene

A

2-Methylthiophene
554-14-3

2-Methylthiophene

B

3,4-dimethylthiophene
632-15-5

3,4-dimethylthiophene

C

2,5-DIMETHYLTHIOPHENE
638-02-8

2,5-DIMETHYLTHIOPHENE

D

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;A 6.6 % Chromat.
B 2.9 % Chromat.
C 3.5 % Chromat.
D 9.5 % Chromat.
2,5-DIMETHYLTHIOPHENE
638-02-8

2,5-DIMETHYLTHIOPHENE

A

thiophene
188290-36-0

thiophene

B

2-Methylthiophene
554-14-3

2-Methylthiophene

C

2,3-dimethylthiophene
632-16-6

2,3-dimethylthiophene

D

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;A 2.0 % Chromat.
B 15.4 % Chromat.
C 1.0 % Chromat.
D 2.3 % Chromat.
isopropyl vinyl sulfide
18888-46-5

isopropyl vinyl sulfide

A

thiophene
188290-36-0

thiophene

B

2-Methylthiophene
554-14-3

2-Methylthiophene

C

3-Methylthiophene
616-44-4

3-Methylthiophene

D

toluene
108-88-3

toluene

E

benzene
71-43-2

benzene

Conditions
ConditionsYield
at 550℃; Product distribution;
bis-(1-propenyl) sulfide
33922-80-4

bis-(1-propenyl) sulfide

A

thiophene
188290-36-0

thiophene

B

2-Methylthiophene
554-14-3

2-Methylthiophene

C

2-ethylthiophene
872-55-9

2-ethylthiophene

D

3-Methylthiophene
616-44-4

3-Methylthiophene

E

Prop-1-en-1-thiol
925-89-3

Prop-1-en-1-thiol

F

benzene
71-43-2

benzene

Conditions
ConditionsYield
at 520℃; Product distribution; Mechanism; reaction in the presence of dimethyl selenide, 2-halothiophenes and acetylene, var. temp.;
propyl vinyl sulfide
16330-21-5

propyl vinyl sulfide

A

thiophene
188290-36-0

thiophene

B

2-Methylthiophene
554-14-3

2-Methylthiophene

C

3-Methylthiophene
616-44-4

3-Methylthiophene

D

toluene
108-88-3

toluene

E

benzene
71-43-2

benzene

Conditions
ConditionsYield
at 550℃; Product distribution;
pentane
109-66-0

pentane

A

thiophene
188290-36-0

thiophene

B

2-Methylthiophene
554-14-3

2-Methylthiophene

C

3-Methylthiophene
616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With cerium(IV) oxide; aluminum oxide; chromium(III) oxide; lanthanum(III) oxide; praseodymium(III) oxide; Nd3O3; hydrogen sulfide; potassium oxide at 550℃; under 760 Torr; Yield given. Yields of byproduct given;
With hydrogen sulfide; cerium(IV) oxide; chromium(III) oxide; lanthanum(III) oxide; neodymium(III) oxide; praseodymium(III) oxide; potassium oxide at 550℃; Product distribution; Further Variations:; Catalysts;
pentane
109-66-0

pentane

A

thiophene
188290-36-0

thiophene

B

2-Methylthiophene
554-14-3

2-Methylthiophene

C

3-Methylthiophene
616-44-4

3-Methylthiophene

D

2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

E

(Z)-pent-2-ene
627-20-3

(Z)-pent-2-ene

F

(E)-pent-2-ene
646-04-8

(E)-pent-2-ene

Conditions
ConditionsYield
With hydrogen sulfide; ferrisilicate at 500℃; for 1h; Product distribution; other temperatures, other volume feed rates of n-pentane, other H2S/n-pentane molar ratios, other reaction times;A 0.3 % Chromat.
B 12.2 % Chromat.
C 1.7 % Chromat.
D n/a
E n/a
F n/a
vinyl ethylsulfide
627-50-9

vinyl ethylsulfide

A

thiophene
188290-36-0

thiophene

B

2-Methylthiophene
554-14-3

2-Methylthiophene

C

3-Methylthiophene
616-44-4

3-Methylthiophene

D

toluene
108-88-3

toluene

E

benzene
71-43-2

benzene

Conditions
ConditionsYield
at 550℃; Product distribution;
2-(1-methylpropenyl)-1,3-dithiolane 1,1-dioxide

2-(1-methylpropenyl)-1,3-dithiolane 1,1-dioxide

A

3-Methylthiophene
616-44-4

3-Methylthiophene

B

3,4,7,8,11,12-hexamethyl-1,5,9-trithiacyclododeca-2,6,10-triene

3,4,7,8,11,12-hexamethyl-1,5,9-trithiacyclododeca-2,6,10-triene

Conditions
ConditionsYield
at 430 - 600℃;
3-Methylthiophene
616-44-4

3-Methylthiophene

4-heptanone
123-19-3

4-heptanone

2-(4-hydroxy-4-heptyl)-4-methylthiophene
1567323-42-5

2-(4-hydroxy-4-heptyl)-4-methylthiophene

Conditions
ConditionsYield
Stage #1: 3-Methylthiophene With n-butyllithium In diethyl ether; hexane for 1h; Reflux;
Stage #2: 4-heptanone In diethyl ether at 20℃; for 1h;
100%
3-Methylthiophene
616-44-4

3-Methylthiophene

2-bromo-3-methylthiophene
14282-76-9

2-bromo-3-methylthiophene

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrahydrofuran Inert atmosphere;99%
With N-Bromosuccinimide99%
With N-Bromosuccinimide In acetic acid for 0.416667h;97.9%
3-Methylthiophene
616-44-4

3-Methylthiophene

2,5-dibromo-3-methylthiophene
13191-36-1

2,5-dibromo-3-methylthiophene

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrahydrofuran Inert atmosphere;99%
With benzyltrimethylazanium tribroman-2-uide; zinc(II) chloride In acetic acid for 15h; Ambient temperature;97%
With potassium bromide In water; acetic acid at 30℃; for 0.25h; Temperature;94%
3-Methylthiophene
616-44-4

3-Methylthiophene

[hydroxy(tosyloxy)iodo]benzene
27126-76-7

[hydroxy(tosyloxy)iodo]benzene

(3-methyl-2-thienyl)(phenyl)iodonium tosylate
91228-41-0

(3-methyl-2-thienyl)(phenyl)iodonium tosylate

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 20℃; for 3h;98%
In 2,2,2-trifluoroethanol at 20℃; for 3h;98%
In 2,2,2-trifluoroethanol at 0 - 20℃;98%
In chloroform for 2h; Heating;78.1%
3-Methylthiophene
616-44-4

3-Methylthiophene

[hydroxy(tosyloxy)iodo]benzene
27126-76-7

[hydroxy(tosyloxy)iodo]benzene

(3-methyl-2-thienyl)(phenyl)iodonium tosylate
1118904-87-2

(3-methyl-2-thienyl)(phenyl)iodonium tosylate

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 20℃; for 2h;98%
In 2,2,2-trifluoroethanol at 20℃; for 2h;84%
3-Methylthiophene
616-44-4

3-Methylthiophene

3'-[4-(t-butyldimethylsilyloxy)-3-methylphenyl]pentan-3-ol
633337-85-6

3'-[4-(t-butyldimethylsilyloxy)-3-methylphenyl]pentan-3-ol

3'-[4-(hydroxy)-3-methylphenyl]-3'-[4-methylthiophen-2-yl]pentane
633337-86-7

3'-[4-(hydroxy)-3-methylphenyl]-3'-[4-methylthiophen-2-yl]pentane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at -78 - 20℃; for 6.75h;95%
With boron trifluoride diethyl etherate at -78 - 20℃; for 6.75h; Product distribution / selectivity;95%
3-Methylthiophene
616-44-4

3-Methylthiophene

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-(4-methylthiophen-2-yl)benzonitrile
1101167-54-7

4-(4-methylthiophen-2-yl)benzonitrile

Conditions
ConditionsYield
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;
Stage #2: With zinc(II) chloride In tetrahydrofuran; diethyl ether; hexane at 0℃; for 4h; Inert atmosphere;
Stage #3: 4-bromobenzenecarbonitrile With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether; hexane at 20 - 50℃; Inert atmosphere;
95%
phthalic anhydride
85-44-9

phthalic anhydride

3-Methylthiophene
616-44-4

3-Methylthiophene

2-(4-methylthiophene-2-carbonyl)benzoic acid

2-(4-methylthiophene-2-carbonyl)benzoic acid

Conditions
ConditionsYield
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethylpiperidin-4-yl heptanoate; isopropylmagnesium chloride In tetrahydrofuran at 66℃; for 23h;
Stage #2: phthalic anhydride With hydrogenchloride In tetrahydrofuran; water at -20 - 20℃;
94%
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethyl-piperidine; isopropylmagnesium chloride In tetrahydrofuran at 66℃; for 23h; Inert atmosphere;
Stage #2: phthalic anhydride In tetrahydrofuran at -25 - -20℃; for 1.08333h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at -20 - 20℃; pH=2; regioselective reaction;
89.7%
With aluminium trichloride; nitrobenzene
3-Methylthiophene
616-44-4

3-Methylthiophene

2-iodo-3-methylthiophene
16494-40-9

2-iodo-3-methylthiophene

Conditions
ConditionsYield
With iodine; mercury(II) oxide94%
With iodine; mercury(II) oxide In benzene for 0.5h; Ambient temperature;94%
With iodine; mercury(II) oxide In benzene Iodination;79%
3-Methylthiophene
616-44-4

3-Methylthiophene

2,3,5-triiodo-4-methyl-thiophene
16488-62-3

2,3,5-triiodo-4-methyl-thiophene

Conditions
ConditionsYield
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 15h; Ambient temperature;94%
With mercury(II) diacetate; iodine; acetic acid
3-Methylthiophene
616-44-4

3-Methylthiophene

pentaamminetrifluoromethanesulfonato osmium(III) trifluoromethanesulfonate
83781-30-0

pentaamminetrifluoromethanesulfonato osmium(III) trifluoromethanesulfonate

4,5-η2-[Os(NH3)5]-3-methylthiophene triflate

4,5-η2-[Os(NH3)5]-3-methylthiophene triflate

Conditions
ConditionsYield
With Mg In N,N-dimethyl acetamide Kinetics; N2-atmosphere;93%
With Z/Hg In methanol Kinetics; N2-atmosphere;93%
In [D3]acetonitrile Kinetics; N2-atmosphere; -40°C; not isolated; detd. by (1)H NMR spectroscopy;
3-Methylthiophene
616-44-4

3-Methylthiophene

1,1,1,3,5,5,5-heptamethyltrisiloxan
1873-88-7

1,1,1,3,5,5,5-heptamethyltrisiloxan

1,1,1,3,5,5,5-heptamethyl-3-(4-methylthiophen-2-yl)trisiloxane

1,1,1,3,5,5,5-heptamethyl-3-(4-methylthiophen-2-yl)trisiloxane

Conditions
ConditionsYield
With tert-butylethylene; C25H40O2P2Ru In neat (no solvent) at 120℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;93%
Stage #1: 1,1,1,3,5,5,5-heptamethyltrisiloxan With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; C25H35N3; cyclohexene In tetrahydrofuran Inert atmosphere; Glovebox;
Stage #2: 3-Methylthiophene In tetrahydrofuran at 65℃; for 26h; Sealed tube; Inert atmosphere; regioselective reaction;
89%
3-Methylthiophene
616-44-4

3-Methylthiophene

3-methyl-2,5-diiodothiophene
16488-60-1

3-methyl-2,5-diiodothiophene

Conditions
ConditionsYield
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 4h; Ambient temperature;92%
With sulfuric acid; iodine; iodic acid In tetrachloromethane; water; acetic acid for 4h; Heating;64%
3-Methylthiophene
616-44-4

3-Methylthiophene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-methylthiophene-2-carbaldehyde
6030-36-0

4-methylthiophene-2-carbaldehyde

Conditions
ConditionsYield
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
92%
Stage #1: 3-Methylthiophene With n-butyllithium In tetrahydrofuran at -65℃; for 0.5h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -65℃; for 2h;
90%
With n-butyllithium In diethyl ether at 20℃; for 1.5h;84%
3-Methylthiophene
616-44-4

3-Methylthiophene

phenylthallium(III) (1,4,7,10,13,16-hexaoxacyclooctadecane)diperchlorate

phenylthallium(III) (1,4,7,10,13,16-hexaoxacyclooctadecane)diperchlorate

(18-crown-6)phenyl(4-methyl-2-thienyl)thallium(III) perchlorate

(18-crown-6)phenyl(4-methyl-2-thienyl)thallium(III) perchlorate

Conditions
ConditionsYield
In acetonitrile addn. of solvent and thiophene to complex, degassed three times, sealed (vac.), heated at 60°C for 24 h in the dark; addn. of Et2O, pptn., filtered, addn. of Et2O to CH2Cl2 soln., filtered, dissolved in CH3CN, addn. of Et2O, recrystd. (CH2Cl2/Et2O); elem. anal.;92%
3-Methylthiophene
616-44-4

3-Methylthiophene

diphenyltin(IV) dichloride
1135-99-5

diphenyltin(IV) dichloride

bis(4-methyl-2-thienyl)diphenyltin(IV)
117013-09-9

bis(4-methyl-2-thienyl)diphenyltin(IV)

Conditions
ConditionsYield
With n-C4H9Li In not given reflux 3 h;92%
With PhLi In not given reflux 3 h; elem. anal.;79%
3-Methylthiophene
616-44-4

3-Methylthiophene

C16H21IO5S

C16H21IO5S

(3-methyl-2-thienyl)(phenyl)iodonium (+/-)-10-camphorsulfonate

(3-methyl-2-thienyl)(phenyl)iodonium (+/-)-10-camphorsulfonate

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 20℃; for 3h;92%
3-Methylthiophene
616-44-4

3-Methylthiophene

C16H21IO5S

C16H21IO5S

(3-methyl-2-thienyl)(phenyl)iodonium 10-camphorsulfonate

(3-methyl-2-thienyl)(phenyl)iodonium 10-camphorsulfonate

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 20℃; for 3h;92%
3-Methylthiophene
616-44-4

3-Methylthiophene

diphenyliodonium tetrafluoroborate

diphenyliodonium tetrafluoroborate

3-methyl-4-phenylthiophene
16939-15-4

3-methyl-4-phenylthiophene

Conditions
ConditionsYield
With 5%-palladium/activated carbon In ethanol at 60℃; for 22h; regioselective reaction;92%
With palladium In tetrahydrofuran at 60℃; for 24h;71%
3-Methylthiophene
616-44-4

3-Methylthiophene

iodobenzene
591-50-4

iodobenzene

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

C7H7O3S(1-)*C17H14IS(1+)

C7H7O3S(1-)*C17H14IS(1+)

Conditions
ConditionsYield
Stage #1: iodobenzene With peracetic acid; acetic acid In dichloromethane; 2,2,2-trifluoroethanol at 35℃; for 1h;
Stage #2: 3-Methylthiophene; toluene-4-sulfonic acid In dichloromethane; 2,2,2-trifluoroethanol at 20℃; for 3h;
91%
3-Methylthiophene
616-44-4

3-Methylthiophene

3-Bromomethylthiophene
34846-44-1

3-Bromomethylthiophene

Conditions
ConditionsYield
With N-Bromosuccinimide; dihydrogen peroxide In tetrachloromethane90%
With N-Bromosuccinimide; dibenzoyl peroxide In benzene for 0.5h; Heating;88%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2h; Reflux;87%
3-Methylthiophene
616-44-4

3-Methylthiophene

2-diazocyclohexane-1,3-dione
1460-08-8

2-diazocyclohexane-1,3-dione

3-Hydroxy-2-(4-methylthien-2-yl)cyclohex-2-enone

3-Hydroxy-2-(4-methylthien-2-yl)cyclohex-2-enone

Conditions
ConditionsYield
dirhodium tetraacetate In fluorobenzene for 15h; Ambient temperature;90%
3-Methylthiophene
616-44-4

3-Methylthiophene

A

2-iodo-3-methylthiophene
16494-40-9

2-iodo-3-methylthiophene

B

3-methyl-2,5-diiodothiophene
16488-60-1

3-methyl-2,5-diiodothiophene

Conditions
ConditionsYield
With ammonium iodide; dihydrogen peroxide In water; acetic acid for 20h; Green chemistry; regioselective reaction;A 90%
B 10%
3-Methylthiophene
616-44-4

3-Methylthiophene

iodobenzene
591-50-4

iodobenzene

2-phenyl-4-methylthiophene
14300-29-9

2-phenyl-4-methylthiophene

Conditions
ConditionsYield
Stage #1: 3-Methylthiophene With n-butyllithium In diethyl ether; hexane for 1h; Heating;
Stage #2: With Trimethyl borate In diethyl ether; hexane at 20℃; for 1h;
Stage #3: iodobenzene With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; diethyl ether; hexane for 5h; Heating;
89%
3-Methylthiophene
616-44-4

3-Methylthiophene

(mesyloxyhydroxyiodo)benzene
105551-42-6

(mesyloxyhydroxyiodo)benzene

(3-methyl-2-thienyl)(phenyl)iodonium methanesulfonate

(3-methyl-2-thienyl)(phenyl)iodonium methanesulfonate

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 20℃; for 3h;89%
3-Methylthiophene
616-44-4

3-Methylthiophene

(mesyloxyhydroxyiodo)benzene
105551-42-6

(mesyloxyhydroxyiodo)benzene

(3-methyl-2-thienyl)(phenyl)iodonium methanesulfonate
1205744-68-8

(3-methyl-2-thienyl)(phenyl)iodonium methanesulfonate

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 20℃; for 3h;89%
3-Methylthiophene
616-44-4

3-Methylthiophene

4-bromobenzenesulfonyl chloride
98-58-8

4-bromobenzenesulfonyl chloride

3-(4-bromophenyl)-4-methylthiophene

3-(4-bromophenyl)-4-methylthiophene

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); lithium carbonate In 1,4-dioxane at 140℃; for 40h; Inert atmosphere; Schlenk technique; regioselective reaction;89%
isoquinoline N-oxide
1532-72-5

isoquinoline N-oxide

3-Methylthiophene
616-44-4

3-Methylthiophene

3-(thiopheno-2-methoxy)quinazolino-4(3H)-one

3-(thiopheno-2-methoxy)quinazolino-4(3H)-one

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; copper(II) sulfate; sodium iodide In decane; dichloromethane at 70℃; for 8h;89%

616-44-4Relevant articles and documents

-

Sheppard et al.

, p. 1355 (1934)

-

Catalytic Synthesis of Methylthiophenes

Mashkina,Khairulina

, p. 1794 - 1797 (2019/03/26)

The gas-phase reaction of dimethyl disulfide with thiophene over Co/HZSM-5 catalyst in a helium medium under atmospheric pressure at 250–350°C gave a mixture of mono-, di-, tri-, and tetramethylthiophenes with an overall selectivity of 94–96%.

Preparation of an Arenylmethylzinc Reagent with Functional Groups by Chemoselective Cross-Coupling Reaction of Bis(iodoazincio)methane with Iodoarenes

Shimada, Yukako,Haraguchi, Ryosuke,Matsubara, Seijiro

, p. 2395 - 2398 (2015/10/19)

Palladium-catalyzed cross-coupling reaction of bis(iodozincio)methane with iodoarenes carrying various functionalities such as ester, boryl, cyano, and halo groups proceeded chemoselectively to give the corresponding arenylmethylzinc species efficiently. The moderate reactivity of the gem-dizinc reagent imparted functional group tolerance to the process. The transformations from iodoheteroarenes were also performed; in the case of iodopyridine derivatives, the nickel-catalyzed reaction gave the corresponding organozinc species efficiently. The obtained arenylmethylzinc species underwent the copper-mediated coupling reaction with a range of organic halides.

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