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25016-01-7

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25016-01-7 Usage

Description

5-Bromo-2-anisaldehyde, also known as 5-Bromo-2-methoxybenzaldehyde, is a light yellow crystalline powder with distinct spectral properties. It is an organic compound derived from anisaldehyde, featuring a bromine atom at the 5th position and a methoxy group at the 2nd position on the benzene ring. 5-Bromo-2-anisaldehyde is known for its unique chemical and physical properties, making it a versatile molecule for various applications across different industries.

Uses

Used in Chemical Synthesis:
5-Bromo-2-anisaldehyde is used as a key intermediate in the synthesis of various organic compounds, particularly those with potential applications in pharmaceuticals, agrochemicals, and materials science. Its unique structure allows for further functionalization and modification, making it a valuable building block in the development of new molecules with specific properties and functions.
Used in Pharmaceutical Industry:
5-Bromo-2-anisaldehyde is used as a starting material for the development of new drugs and pharmaceutical agents. Its chemical properties enable the creation of molecules with potential therapeutic applications, such as anti-inflammatory, analgesic, or anti-cancer agents. The compound's versatility in chemical reactions allows for the design and synthesis of novel drug candidates with improved efficacy and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical industry, 5-Bromo-2-anisaldehyde is used as a precursor for the synthesis of bioactive compounds with potential applications as pesticides, herbicides, or insecticides. Its unique structure can be exploited to create molecules with enhanced biological activity and selectivity, leading to more effective and environmentally friendly agrochemical products.
Used in Materials Science:
5-Bromo-2-anisaldehyde is used as a component in the development of advanced materials with specific properties, such as optical, electronic, or magnetic functionalities. Its incorporation into polymers, coatings, or other materials can lead to the creation of novel materials with improved performance characteristics, such as enhanced stability, durability, or responsiveness to external stimuli.
Used in Research and Development:
5-Bromo-2-anisaldehyde is used as a research tool in academic and industrial laboratories for the study of various chemical and physical phenomena. Its unique properties make it an interesting subject for investigations into reaction mechanisms, molecular interactions, and the development of new synthetic methods or techniques.

Check Digit Verification of cas no

The CAS Registry Mumber 25016-01-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,0,1 and 6 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 25016-01:
(7*2)+(6*5)+(5*0)+(4*1)+(3*6)+(2*0)+(1*1)=67
67 % 10 = 7
So 25016-01-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H7BrO2/c1-11-8-3-2-7(9)4-6(8)5-10/h2-5H,1H3

25016-01-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A19396)  5-Bromo-2-methoxybenzaldehyde, 98+%   

  • 25016-01-7

  • 25g

  • 569.0CNY

  • Detail
  • Alfa Aesar

  • (A19396)  5-Bromo-2-methoxybenzaldehyde, 98+%   

  • 25016-01-7

  • 100g

  • 1509.0CNY

  • Detail
  • Alfa Aesar

  • (A19396)  5-Bromo-2-methoxybenzaldehyde, 98+%   

  • 25016-01-7

  • 500g

  • 6037.0CNY

  • Detail

25016-01-7Synthetic route

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

methyl iodide
74-88-4

methyl iodide

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
Stage #1: 5-bromosalicyclaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 21℃; Inert atmosphere;
98%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 15h;98%
5-bromo-2-methoxy-benzyl alcohol
80866-82-6

5-bromo-2-methoxy-benzyl alcohol

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In neat (no solvent) at 80℃; for 18h; Green chemistry;97%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dimethyl sulfoxide; ethyl acetate at 0 - 20℃; Inert atmosphere;
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With N-Bromosuccinimide; 1-n-butyl-3-methylimidazolim bromide for 0.25h; Ionic liquid; regioselective reaction;95%
With iodine pentoxide; potassium bromide In water at 20℃; for 23h; regioselective reaction;94%
With poly(N-bromobenzene-1,3-disulfonylamide) In dichloromethane at 40℃; for 1.5h;89%
dimethyl sulfate
77-78-1

dimethyl sulfate

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In acetone for 2h;95%
With potassium carbonate In acetone at 20℃;93%
With sodium carbonate In acetone for 8h; Inert atmosphere; Reflux;92%
(2-methoxyphenyl)methanol
612-16-8

(2-methoxyphenyl)methanol

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With bis(collidine)bromine(I) hexafluorophosphate In dichloromethane at 20℃; for 5h;95%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In dichloromethane at 25℃; for 0.5h; chemoselective reaction;66 %Chromat.
2-methyl-4-bromoanisole
14804-31-0

2-methyl-4-bromoanisole

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 3.5h; Irradiation; Green chemistry;91%
With pyridine; dipotassium peroxodisulfate; copper(I) sulfate In water; acetonitrile at 65 - 70℃; for 3h;51%
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrachloromethane / 5 h / 20 - 30 °C / Irradiation
2: 4-methylmorpholine N-oxide / 2 h / 20 °C / Reflux
View Scheme
2,4-dibromoanisole
21702-84-1

2,4-dibromoanisole

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

N,N-dimethyl-formamide

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
Stage #1: 2,4-dibromoanisole With n-butyllithium In diethyl ether at -78℃; for 0.25h;
Stage #2: N,N-dimethyl-formamide In diethyl ether at -78℃; for 0.25h;
90%
acetone
67-64-1

acetone

dimethyl sulfate
77-78-1

dimethyl sulfate

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

A

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

B

(E)-4-(5-Bromo-2-methoxy-phenyl)-but-3-en-2-one
943768-51-2

(E)-4-(5-Bromo-2-methoxy-phenyl)-but-3-en-2-one

C

4-(5-Bromo-2-methoxy-phenyl)-4-hydroxy-butan-2-one

4-(5-Bromo-2-methoxy-phenyl)-4-hydroxy-butan-2-one

Conditions
ConditionsYield
With potassium carbonate for 15h; Heating;A 5%
B n/a
C 88%
With potassium carbonate for 15h; Heating;
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

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

N,N-dimethyl-formamide

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene With 2-(N,N-dimethylaminomethyl)phenyllithium In tert-butyl methyl ether; cyclohexane at 60℃; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide at 20℃; for 3h;
73.8%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In dichloromethane at -78℃; for 0.166667h; Inert atmosphere; regioselective reaction;61%
titanium tetrachloride In dichloromethane
methanol
67-56-1

methanol

m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With dipotassium peroxodisulfate; palladium diacetate; 3-trifluoromethylaniline In dichloromethane at 60℃; for 24h; Sealed tube;30%
tetramethlyammonium chloride
75-57-0

tetramethlyammonium chloride

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate at 150 - 160℃; for 4h;16%
methanol
67-56-1

methanol

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

A

2,4-dibromoanisole
21702-84-1

2,4-dibromoanisole

B

methyl 5-bromo-2-methoxybenzoate
7120-41-4

methyl 5-bromo-2-methoxybenzoate

C

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With Oxone; sodium bromide In water at 20℃; for 24h;A 15%
B 15%
C 5%
4-bromo-2-(chloromethyl)-1-methoxybenzene
7017-52-9

4-bromo-2-(chloromethyl)-1-methoxybenzene

A

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

B

5-bromo-2-methoxybenzoic acid
2476-35-9

5-bromo-2-methoxybenzoic acid

Conditions
ConditionsYield
With copper(II) nitrate; acetic acid
2-methoxybenzyl bromide
52289-93-7

2-methoxybenzyl bromide

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With sodium periodate; hydrogen cation; lithium bromide Heating;
Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

2-fluoronaphthalene
323-09-1

2-fluoronaphthalene

A

7-fluoro-1-naphthaldehyde

7-fluoro-1-naphthaldehyde

B

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
titanium tetrachloride In dichloromethane
4-bromo-2-(bromomethyl)-1-methoxybenzene
184970-28-3

4-bromo-2-(bromomethyl)-1-methoxybenzene

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With 4-methylmorpholine N-oxide at 20℃; for 2h; Reflux;118.27 mg
dicyanozinc
557-21-1

dicyanozinc

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

5-cyano-2-methoxybenzaldehyde
21962-53-8

5-cyano-2-methoxybenzaldehyde

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In DMF (N,N-dimethyl-formamide) at 20℃; for 3h;99%
With water; tri tert-butylphosphoniumtetrafluoroborate; zinc; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In 1-methyl-pyrrolidin-2-one at 20℃; for 24h;98%
ethyl (diethoxyphosphoryl)methanesulfonate
73300-75-1

ethyl (diethoxyphosphoryl)methanesulfonate

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

C11H13BrO4S

C11H13BrO4S

Conditions
ConditionsYield
Stage #1: ethyl (diethoxyphosphoryl)methanesulfonate With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.25h;
Stage #2: 5-bromo-2-methoxybenzaldehyde In tetrahydrofuran; hexanes at -78 - 20℃; for 1h;
99%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

5-bromo-2-methoxy-3-nitrobenzaldehyde
213620-52-1

5-bromo-2-methoxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With sulfuric acid; nitric acid at -15℃; for 2h;99%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

benzoyl chloride
98-88-4

benzoyl chloride

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

C17H15BrO3
1465765-08-5

C17H15BrO3

Conditions
ConditionsYield
Stage #1: vinyl magnesium bromide; 5-bromo-2-methoxybenzaldehyde In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: benzoyl chloride In tetrahydrofuran at 0 - 20℃; for 15h; Inert atmosphere;
99%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

ethyl-3-(5-bromo-2-methoxyphenyl) acrylate

ethyl-3-(5-bromo-2-methoxyphenyl) acrylate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.5h; Inert atmosphere;
Stage #2: 5-bromo-2-methoxybenzaldehyde In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;
98.99%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

5-bromo-2-methoxy-benzyl alcohol
80866-82-6

5-bromo-2-methoxy-benzyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; water98%
With sodium tetrahydroborate In tetrahydrofuran; methanol for 3h;97.2%
With sodium tetrahydroborate In methanol; water at 20℃; for 24h;94%
ethylene glycol
107-21-1

ethylene glycol

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

2-(5-bromo-2-methoxy-phenyl)-1,3-dioxolane
156603-10-0

2-(5-bromo-2-methoxy-phenyl)-1,3-dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Reflux;98%
With toluene-4-sulfonic acid In toluene Heating;65%
With toluene-4-sulfonic acid In toluene for 2h;
tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

(E)-3-(3-formyl-4-methoxyphenyl)acrylic acid tert-butyl ester

(E)-3-(3-formyl-4-methoxyphenyl)acrylic acid tert-butyl ester

Conditions
ConditionsYield
With 1,3-disubstituted imidazolium bromide; potassium carbonate; palladium diacetate In 1,4-dioxane at 105℃; for 17h; Heck reaction;98%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

5-bromo-2-methoxybenzonitrile
144649-99-0

5-bromo-2-methoxybenzonitrile

Conditions
ConditionsYield
With ammonium iodide In dimethyl sulfoxide at 20℃; for 5h; Electrolysis;98%
With formic acid; hydroxylamine hydrochloride; sodium acetate for 15h; Reflux;97%
With sodium hydroxide; formic acid; hydroxylamine hydrochloride; sodium formate
With sodium hydroxide; hydroxylamine hydrochloride; sodium acetate; acetic anhydride; acetic acid
With sodium hydroxide; hydroxylamine hydrochloride; sodium acetate; acetic anhydride; acetic acid
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

4-bromo-2-(diethoxymethyl)-1-methoxybenzene
67868-79-5

4-bromo-2-(diethoxymethyl)-1-methoxybenzene

Conditions
ConditionsYield
With zirconium(IV) chloride In ethanol at 20℃;98%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

(1S,2S,3S,5R)-(+)-isopinocampheylamine
13293-47-5

(1S,2S,3S,5R)-(+)-isopinocampheylamine

(1S,2S,3S,5R)-N-(5-bromo-2-methoxybenzyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine

(1S,2S,3S,5R)-N-(5-bromo-2-methoxybenzyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methoxybenzaldehyde; (1S,2S,3S,5R)-(+)-isopinocampheylamine In methanol
Stage #2: With sodium cyanoborohydride; acetic acid In methanol
98%
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

C10H13BrO3

C10H13BrO3

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methoxybenzaldehyde With sodium tetrahydroborate In methanol at 0 - 20℃;
Stage #2: chloromethyl methyl ether With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
98%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

(5-bromo-2-methoxyphenyl)(4-fluorophenyl)methanol
1282796-09-1

(5-bromo-2-methoxyphenyl)(4-fluorophenyl)methanol

Conditions
ConditionsYield
Stage #1: 1-Bromo-4-fluorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3h;
Stage #2: 5-bromo-2-methoxybenzaldehyde In tetrahydrofuran; hexane at 20℃;
97%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

(E)-ethyl 3-(5-bromo-2-methoxyphenyl)acrylate
540778-82-3

(E)-ethyl 3-(5-bromo-2-methoxyphenyl)acrylate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran96%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

(2-methylsulfanylphenyl)boronic acid
168618-42-6

(2-methylsulfanylphenyl)boronic acid

4-methoxy-2'-(methylthio)biphenyl-3-carbaldehyde
923281-46-3

4-methoxy-2'-(methylthio)biphenyl-3-carbaldehyde

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 18h; Heating / reflux;96%
[(p-methylphenyl)sulfonylmethyl]isonitrile
38622-91-2, 36635-61-7

[(p-methylphenyl)sulfonylmethyl]isonitrile

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

C10H8BrNO2
1091618-40-4

C10H8BrNO2

Conditions
ConditionsYield
With potassium carbonate In methanol for 22h; Reflux;96%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

2-(5-bromo-2-methoxyphenyl)-5,5-dimethyl-1,3-dioxane

2-(5-bromo-2-methoxyphenyl)-5,5-dimethyl-1,3-dioxane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Reflux; Dean-Stark;96%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

5-(5-Bromo-2-methoxy-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione
117646-13-6

5-(5-Bromo-2-methoxy-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 12h; Ambient temperature;95%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

(diisopropoxyphosphorylmethanesulfonylmethanesulfonylmethyl)phosphonic acid diisopropyl ester
312512-49-5

(diisopropoxyphosphorylmethanesulfonylmethanesulfonylmethyl)phosphonic acid diisopropyl ester

bis(4-bromo-2-(2-methanesulfonyl-vinyl)-1-methoxy-benzene)

bis(4-bromo-2-(2-methanesulfonyl-vinyl)-1-methoxy-benzene)

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; lithium bromide In tetrahydrofuran Horner-Emmons-Wadsworth reaction;95%
N-methoxy-N-methyl-2-(triphenylphosphoranylidene)acetamide
129986-67-0

N-methoxy-N-methyl-2-(triphenylphosphoranylidene)acetamide

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

3-(5-bromo-2-methoxyphenyl)-N-methoxy-N-methylacrylamide

3-(5-bromo-2-methoxyphenyl)-N-methoxy-N-methylacrylamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5h;95%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

(E)-methyl 3-(5-bromo-2-methoxyphenyl)acrylate
1528736-46-0

(E)-methyl 3-(5-bromo-2-methoxyphenyl)acrylate

Conditions
ConditionsYield
In toluene Reflux;95%
In toluene Inert atmosphere; Reflux;95%
6-aminocoumarin
14415-44-2

6-aminocoumarin

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

6-(5-bromo-2-methoxybenzylideneamino)-2H-chromen-2-one

6-(5-bromo-2-methoxybenzylideneamino)-2H-chromen-2-one

Conditions
ConditionsYield
With piperidine In ethanol for 6h; Heating;94%
[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]boronic acid
1189060-59-0

[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]boronic acid

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

5-[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]salicylaldehyde
1189060-60-3

5-[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]salicylaldehyde

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; palladium diacetate; sodium hydrogencarbonate; triphenylphosphine In ethanol; water; toluene at 100℃; for 3.5h; Suzuki coupling; Inert atmosphere;94%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

urea
57-13-6

urea

5-ethoxycarbonyl-4-(2-methoxy-5-bromophenyl)-6-methyl-3,4-dihydropyrimidin-2-(1H)-one
313508-33-7

5-ethoxycarbonyl-4-(2-methoxy-5-bromophenyl)-6-methyl-3,4-dihydropyrimidin-2-(1H)-one

Conditions
ConditionsYield
With HPA-montmorillonite-KSF In neat (no solvent) for 1h; Biginelli Pyrimidone Synthesis; Reflux; Green chemistry;94%
With Zn0.9Ni0.1Al2O4 In ethanol for 4h; Biginelli Pyrimidone Synthesis; Reflux;52%
5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

tetramethylammonium trifluoromethanethiolate

tetramethylammonium trifluoromethanethiolate

2-Methoxy-5-(trifluoromethylthio)benzaldehyde

2-Methoxy-5-(trifluoromethylthio)benzaldehyde

Conditions
ConditionsYield
With palladium(l) tri-tert-butylphosphine iodide dimer In toluene at 80℃;94%

25016-01-7Relevant articles and documents

Electricity Driven 1,3-Oxohydroxylation of Donor-Acceptor Cyclopropanes: a Mild and Straightforward Access to β-Hydroxy Ketones

Banerjee, Prabal,Maajid Taily, Irshad,Saha, Debarshi

supporting information, p. 5053 - 5057 (2021/09/30)

An unprecedented external oxidant-free electrochemical protocol for 1, 3-oxohydroxylation of donor-acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π-electron cloud of the aryl ring to cleave the strained Csp3?Csp3 bond of cyclopropane to afford the β-hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.

V2O5@TiO2 Catalyzed Green and Selective Oxidation of Alcohols, Alkylbenzenes and Styrenes to Carbonyls

Upadhyay, Rahul,Kumar, Shashi,Maurya, Sushil K.

, p. 3594 - 3600 (2021/07/02)

The versatile application of different functional groups such as alcohols (1° and 2°), alkyl arenes, and (aryl)olefins to construct carbon-oxygen bond via oxidation is an area of intense research. Here, we report a reusable heterogeneous V2O5@TiO2 catalyzed selective oxidation of various functionalities utilizing different mild and eco-compatible oxidants under greener reaction conditions. The method was successfully applied for the alcohol oxidation, oxidative scission of styrenes, and benzylic C?H oxidation to their corresponding aldehydes and ketones. The utilization of mild and eco-friendly oxidizing reagents such as K2S2O8, H2O2 (30 % aq.), TBHP (70 % aq.), broad substrate scope, gram-scale synthesis, and catalyst recyclability are notable features of the developed protocol.

Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes

Li, Feng,Zhou, Yirong,Yang, Heng,Wang, Ziqi,Yu, Qinqin,Zhang, Fang-Lin

supporting information, p. 3692 - 3695 (2019/05/24)

We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.

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