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5287-45-6

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5287-45-6 Usage

Description

3-Methyl-2-buten-1-thiol, also known as isopulegol thiol, is a volatile organic sulfur compound characterized by its distinctive, strong odor. It is a naturally occurring compound found in various plants and is known for its significant contribution to the aroma of coffee. As a yellow liquid, it possesses unique chemical properties that make it a valuable ingredient in the flavor and fragrance industry.

Uses

Used in Flavor and Fragrance Industry:
3-Methyl-2-buten-1-thiol is used as an aroma compound for its ability to enhance and provide a rich, complex scent to various products. Its strong odor makes it an essential component in the creation of artificial coffee flavors and fragrances, where it helps to mimic the natural aroma of coffee beans.
Used in Food Industry:
In the food industry, 3-Methyl-2-buten-1-thiol is used as a flavoring agent to impart a unique taste and aroma to a variety of products. Its characteristic smell and taste make it a popular choice for adding depth and complexity to the flavor profiles of different food items, particularly those with coffee or roasted notes.
Used in Coffee Production:
3-Methyl-2-buten-1-thiol plays a crucial role in the coffee production process, as it is one of the key compounds responsible for the distinct aroma of coffee. It is used to enhance the natural flavors and aromas of coffee beans, making it an important ingredient in the development of coffee products, from instant coffee to specialty blends.
Used in Spice Industry:
The spice industry also utilizes 3-Methyl-2-buten-1-thiol for its potent and distinctive odor. It is employed as a component in the formulation of various spice blends and seasonings, where it adds a unique and rich flavor profile to the final product. This application helps to create a more diverse and interesting range of spices for use in the culinary world.

Check Digit Verification of cas no

The CAS Registry Mumber 5287-45-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,2,8 and 7 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 5287-45:
(6*5)+(5*2)+(4*8)+(3*7)+(2*4)+(1*5)=106
106 % 10 = 6
So 5287-45-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H10S/c1-5(2)3-4-6/h3,6H,4H2,1-2H3

5287-45-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Methyl-2-buten-1-thiol, Preparation Kit

1.2 Other means of identification

Product number -
Other names 3-methylbut-2-ene-1-thiol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:5287-45-6 SDS

5287-45-6Synthetic route

thiourea
17356-08-0

thiourea

prenyl bromide
870-63-3

prenyl bromide

prenyl mercaptan
5287-45-6

prenyl mercaptan

Conditions
ConditionsYield
In ethanol at 80℃; for 3h;83%
3-Methylthiophene
616-44-4

3-Methylthiophene

prenyl mercaptan
5287-45-6

prenyl mercaptan

Conditions
ConditionsYield
With methanol; ammonia; sodium
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

prenyl mercaptan
5287-45-6

prenyl mercaptan

Conditions
ConditionsYield
With sulfur at 170℃;
dithiocarbamic acid
594-07-0

dithiocarbamic acid

prenyl bromide
870-63-3

prenyl bromide

prenyl mercaptan
5287-45-6

prenyl mercaptan

Conditions
ConditionsYield
With ammonia beim Erwaermen des Reaktionsprodukts mit Alkalilauge;
isoprene
78-79-5

isoprene

prenyl mercaptan
5287-45-6

prenyl mercaptan

Conditions
ConditionsYield
(i) thiourea, aq. HBr, (ii) aq. TsOH, (iii) aq. NaOH; Multistep reaction;
S-methyl S-<1-(3-methyl-2-butenyl)>dithiocarbonate

S-methyl S-<1-(3-methyl-2-butenyl)>dithiocarbonate

prenyl mercaptan
5287-45-6

prenyl mercaptan

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane for 2h; Heating;
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

sulfur

sulfur

prenyl mercaptan
5287-45-6

prenyl mercaptan

Conditions
ConditionsYield
at 170℃; bei laengerer Reaktionsdauer;
prenyl mercaptan
5287-45-6

prenyl mercaptan

3,3,3-trichloro-1-nitropropene
763-16-6

3,3,3-trichloro-1-nitropropene

(3-methylbut-2-enyl)(1,1,1-trichloro-3-nitropropan-2yl)sulfane

(3-methylbut-2-enyl)(1,1,1-trichloro-3-nitropropan-2yl)sulfane

Conditions
ConditionsYield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 6h;84%
prenyl mercaptan
5287-45-6

prenyl mercaptan

5,5,5-trichloro-pent-3-en-2-one
1552-26-7

5,5,5-trichloro-pent-3-en-2-one

5,5,5-trichloro-4-(3-methylbut-2-enylthio)pentan-2-one

5,5,5-trichloro-4-(3-methylbut-2-enylthio)pentan-2-one

Conditions
ConditionsYield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 8h;82%
prenyl mercaptan
5287-45-6

prenyl mercaptan

4,4,4-trichloro-crotononitrile
14252-04-1

4,4,4-trichloro-crotononitrile

4,4,4-trichloro-3-(3-methylbut-2-enylthio)butanenitrile

4,4,4-trichloro-3-(3-methylbut-2-enylthio)butanenitrile

Conditions
ConditionsYield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 12h;81%
prenyl mercaptan
5287-45-6

prenyl mercaptan

4,4,4-trichloro-1-phenyl-but-2-en-1-one
21100-66-3

4,4,4-trichloro-1-phenyl-but-2-en-1-one

4,4,4-trichloro-3-(3-methylbut-2-enylthio)-1-phenylbutan-1-one

4,4,4-trichloro-3-(3-methylbut-2-enylthio)-1-phenylbutan-1-one

Conditions
ConditionsYield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 8h;80%
prenyl mercaptan
5287-45-6

prenyl mercaptan

phenylacetylene
536-74-3

phenylacetylene

3-Isopropyl-4-phenyl-2,3-dihydro-thiophene
112471-59-7

3-Isopropyl-4-phenyl-2,3-dihydro-thiophene

Conditions
ConditionsYield
With triethyl borane In hexane; benzene77%
prenyl mercaptan
5287-45-6

prenyl mercaptan

C5H5Cl3O2

C5H5Cl3O2

methyl 4,4,4-trichloro-3-(3-methylbut-2-enylthio)butanoate

methyl 4,4,4-trichloro-3-(3-methylbut-2-enylthio)butanoate

Conditions
ConditionsYield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 8h;68%
prenyl mercaptan
5287-45-6

prenyl mercaptan

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

C8H14O2S

C8H14O2S

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -1 - 20℃; for 1h; Inert atmosphere;66%
prenyl mercaptan
5287-45-6

prenyl mercaptan

3-(ethoxycarbonyl)-4a-acetoxy-4,4a,9,9a-tetrahydro-1,2-oxazino<5,6-b>indole
106040-12-4

3-(ethoxycarbonyl)-4a-acetoxy-4,4a,9,9a-tetrahydro-1,2-oxazino<5,6-b>indole

ethyl α-(hydroxyimino)-β-<2-((3-methyl-2-butenyl)thio)indol-3-yl>propanoate
106040-09-9

ethyl α-(hydroxyimino)-β-<2-((3-methyl-2-butenyl)thio)indol-3-yl>propanoate

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0℃; for 3h;64%
prenyl mercaptan
5287-45-6

prenyl mercaptan

phenyl isocyanate
103-71-9

phenyl isocyanate

S-(3-methylbut-2-en-1-yl) phenylcarbamothioate

S-(3-methylbut-2-en-1-yl) phenylcarbamothioate

Conditions
ConditionsYield
Stage #1: prenyl mercaptan With potassium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Glovebox;
Stage #2: phenyl isocyanate In tetrahydrofuran for 6h; Glovebox;
44%
prenyl mercaptan
5287-45-6

prenyl mercaptan

β-3,4-epithiocarane
170716-51-5

β-3,4-epithiocarane

A

4α-prenylthiocarane-3β-thiol

4α-prenylthiocarane-3β-thiol

B

C30H50S4

C30H50S4

Conditions
ConditionsYield
With sodium ethanolate for 15h; Ambient temperature;A 42%
B 36%
prenyl mercaptan
5287-45-6

prenyl mercaptan

1-dodecyne
765-03-7

1-dodecyne

4-Decyl-3-isopropyl-2,3-dihydro-thiophene
112471-58-6

4-Decyl-3-isopropyl-2,3-dihydro-thiophene

Conditions
ConditionsYield
With triethyl borane In hexane; benzene35%
prenyl mercaptan
5287-45-6

prenyl mercaptan

(2,4-dinitro-phenyl)-(3-methyl-but-2-enyl)-sulfide
5287-48-9

(2,4-dinitro-phenyl)-(3-methyl-but-2-enyl)-sulfide

prenyl mercaptan
5287-45-6

prenyl mercaptan

benzoyl chloride
98-88-4

benzoyl chloride

S-(3-methylbut-2-en-1-yl)benzothioate

S-(3-methylbut-2-en-1-yl)benzothioate

Conditions
ConditionsYield
With sodium hydroxide
Diethyl disulfide
110-81-6

Diethyl disulfide

prenyl mercaptan
5287-45-6

prenyl mercaptan

ethyl-(3-methyl-but-2-enyl)-disulfane
10276-12-7

ethyl-(3-methyl-but-2-enyl)-disulfane

prenyl mercaptan
5287-45-6

prenyl mercaptan

S-methylsulfenyl O-methyl thiocarbonate
55048-60-7

S-methylsulfenyl O-methyl thiocarbonate

methyl-(3-methyl-but-2-enyl)-disulfane
34776-60-8

methyl-(3-methyl-but-2-enyl)-disulfane

prenyl mercaptan
5287-45-6

prenyl mercaptan

bis(3-methyl-2-buten-1-yl)disulfide
24963-39-1

bis(3-methyl-2-buten-1-yl)disulfide

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide
prenyl mercaptan
5287-45-6

prenyl mercaptan

3-methyl-2-(3-methyl-but-2-enylsulfanyl)-butane-1-thiol
29178-27-6

3-methyl-2-(3-methyl-but-2-enylsulfanyl)-butane-1-thiol

Conditions
ConditionsYield
In hexane Irradiation;
prenyl mercaptan
5287-45-6

prenyl mercaptan

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

α-Carbethoxyethyl 3-Methyl-2-butenylsulfid
61740-72-5

α-Carbethoxyethyl 3-Methyl-2-butenylsulfid

Conditions
ConditionsYield
With sodium ethanolate In ethanol
prenyl mercaptan
5287-45-6

prenyl mercaptan

syn-3-(benzyloxy)-3-phenyl-1-(tributylstannyl)-1-propanol

syn-3-(benzyloxy)-3-phenyl-1-(tributylstannyl)-1-propanol

1-(benzyloxy)-4,4-dimethyl-1-phenyl-5-hexane-3-thiol

1-(benzyloxy)-4,4-dimethyl-1-phenyl-5-hexane-3-thiol

Conditions
ConditionsYield
Yield given. Multistep reaction;
prenyl mercaptan
5287-45-6

prenyl mercaptan

chloral
75-87-6

chloral

3-Methyl-1-(1,2,2,2-tetrachloro-ethylsulfanyl)-but-2-ene
85022-07-7

3-Methyl-1-(1,2,2,2-tetrachloro-ethylsulfanyl)-but-2-ene

prenyl mercaptan
5287-45-6

prenyl mercaptan

acetyl chloride
75-36-5

acetyl chloride

ethanethioic acid S-(3-methyl-2-butenyl) ester
33049-93-3

ethanethioic acid S-(3-methyl-2-butenyl) ester

Conditions
ConditionsYield
In pyridine1.0 g
prenyl mercaptan
5287-45-6

prenyl mercaptan

isopentanoyl chloride
108-12-3

isopentanoyl chloride

S-(3-methylbut-2-en-1-yl) 3-methylbutanethioate
75631-91-3

S-(3-methylbut-2-en-1-yl) 3-methylbutanethioate

Conditions
ConditionsYield
In pyridine1.7 g
prenyl mercaptan
5287-45-6

prenyl mercaptan

Chloromethyltrimethylsilane
2344-80-1

Chloromethyltrimethylsilane

3-methyl-1-trimethylsilylmethylthio-2-butene
151108-99-5

3-methyl-1-trimethylsilylmethylthio-2-butene

Conditions
ConditionsYield
With n-butyllithium 1) HMPA, ether, 0 deg C; Yield given. Multistep reaction;

5287-45-6Relevant articles and documents

Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids

Oberhauser, Clara,Harms, Vanessa,Seidel, Katja,Schr?der, Benjamin,Ekramzadeh, Kimia,Beutel, Sascha,Winkler, Sven,Lauterbach, Lukas,Dickschat, Jeroen S.,Kirschning, Andreas

supporting information, p. 11802 - 11806 (2018/09/10)

The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.

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