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644-36-0 Usage

Chemical Properties

white to slightly cream crystalline powder

Uses

Different sources of media describe the Uses of 644-36-0 differently. You can refer to the following data:
1. 2-Methylphenylacetic acid is a ring-substituted phenylacetic acid with auxin activity used as a plant growth regulator.
2. o-Tolylacetic Acid is a ring-substituted phenylacetic acid with auxin activity used as a plant growth regulator.

Check Digit Verification of cas no

The CAS Registry Mumber 644-36-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 4 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 644-36:
(5*6)+(4*4)+(3*4)+(2*3)+(1*6)=70
70 % 10 = 0
So 644-36-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O2/c1-7-4-2-3-5-8(7)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)/p-1

644-36-0 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A15783)  o-Tolylacetic acid, 99%   

  • 644-36-0

  • 5g

  • 212.0CNY

  • Detail
  • Alfa Aesar

  • (A15783)  o-Tolylacetic acid, 99%   

  • 644-36-0

  • 25g

  • 476.0CNY

  • Detail
  • Alfa Aesar

  • (A15783)  o-Tolylacetic acid, 99%   

  • 644-36-0

  • 100g

  • 1814.0CNY

  • Detail

644-36-0SDS

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 2-Methylphenylacetic acid

1.2 Other means of identification

Product number -
Other names 2-(2-methylphenyl)acetic acid

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:644-36-0 SDS

644-36-0Synthetic route

Ru((+)-BINAP)(O2 CCH3)2

Ru((+)-BINAP)(O2 CCH3)2

2-methylenephenylacetic acid

2-methylenephenylacetic acid

argon

argon

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
In methanol100%
2-o-tolylethanol
19819-98-8

2-o-tolylethanol

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With periodic acid; pyridinium chlorochromate In acetonitrile98%
With periodic acid; tripropylammonium fluorochromate (VI) In acetonitrile at 0℃;98%
isochroman-3-one
4385-35-7

isochroman-3-one

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; W(OTf)6; hydrogen; acetic acid at 50℃; under 760.051 Torr; for 12h;98%
With palladium on activated carbon; W(OTf)6; hydrogen In acetic acid at 50℃; under 760.051 Torr; for 12h;97%
ethyl 2-(2-methylphenyl)acetate
40291-39-2

ethyl 2-(2-methylphenyl)acetate

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14;97%
With potassium hydroxide In ethanol at 20℃; for 15h;0.33 g
2-tolylmethylnitrile
22364-68-7

2-tolylmethylnitrile

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 1.25h; Green chemistry;94%
With sulfuric acid; acetic acid
With potassium hydroxide; dihydrogen peroxide Behandlung mit Salzsaeure;
1-(pyrrolidin-1-yl)-2-(o-tolyl)ethan-1-one
512787-29-0

1-(pyrrolidin-1-yl)-2-(o-tolyl)ethan-1-one

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 41h; Heating;91%
2-indanone
615-13-4

2-indanone

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene Reflux;90%
carbon monoxide
201230-82-2

carbon monoxide

2-methylbenzyl bromide
89-92-9

2-methylbenzyl bromide

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 150℃; under 11251.1 Torr; for 6h; Autoclave;89%
With palladium hydroxide, 20 wt% on carbon; tetrabutylammomium bromide; water In tetrahydrofuran at 110℃; under 7500.75 Torr; for 4h; Sealed tube; Autoclave;65%
carbon monoxide
201230-82-2

carbon monoxide

1-chloromethyl-2-methylbenzene
552-45-4

1-chloromethyl-2-methylbenzene

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
Stage #1: carbon monoxide With C28H22CoN4O6 In butan-1-ol at 60℃; under 760.051 Torr; for 2h; Glovebox; High pressure; Green chemistry;
Stage #2: 1-chloromethyl-2-methylbenzene With tetra-(n-butyl)ammonium iodide; sodium hydroxide In butan-1-ol at 60℃; under 760.051 Torr; for 22h; Glovebox; High pressure; Green chemistry; regioselective reaction;
88%
With bis-triphenylphosphine-palladium(II) chloride; tetraethylammonium chloride; sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; under 11251.1 Torr; for 20h; Autoclave; regioselective reaction;83%
With sodium hydroxide; cerium(III) chloride; cetyltrimethylammonim bromide; nickel cyanide In toluene at 85 - 95℃; under 1 Torr; for 7.25h;55%
carbon monoxide
201230-82-2

carbon monoxide

phthalyl alcohol
612-14-6

phthalyl alcohol

A

isochroman-3-one
4385-35-7

isochroman-3-one

B

o-xylene
95-47-6

o-xylene

C

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;A 88%
B n/a
C 9%
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 120℃; under 68400 Torr; for 42h; Carbonylation; reduction;A 13%
B n/a
C 52%
carbon monoxide
201230-82-2

carbon monoxide

Triethyl-(2-methyl-benzyl)-ammonium; chloride
85267-32-9

Triethyl-(2-methyl-benzyl)-ammonium; chloride

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With sodium hydroxide; dicobalt octacarbonyl at 65℃; Irradiation;85%
carbon monoxide
201230-82-2

carbon monoxide

Triethyl-(2-methyl-benzyl)-ammonium; bromide
85267-31-8

Triethyl-(2-methyl-benzyl)-ammonium; bromide

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With sodium hydroxide; dicobalt octacarbonyl at 65℃; Irradiation;85%
carbon dioxide
124-38-9

carbon dioxide

N,N,N-trimethyl-1-(o-tolyl)methanaminium iodide
117867-97-7

N,N,N-trimethyl-1-(o-tolyl)methanaminium iodide

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; N,N,N-trimethyl-1-(o-tolyl)methanaminium iodide With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex In N,N-dimethyl-formamide at 90℃; under 760.051 Torr; for 72h; Schlenk technique;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; Schlenk technique;
82%
formic acid
64-18-6

formic acid

1-chloromethyl-2-methylbenzene
552-45-4

1-chloromethyl-2-methylbenzene

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; palladium diacetate In N,N-dimethyl-formamide at 115℃; for 12h; Inert atmosphere;80%
carbon monoxide
201230-82-2

carbon monoxide

2-methylbenzyl bromide
89-92-9

2-methylbenzyl bromide

A

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

B

1,2-bis(2-methylphenyl)ethane
952-80-7

1,2-bis(2-methylphenyl)ethane

C

1,3-bis(2-methylphenyl)-2-propanone
23592-92-9

1,3-bis(2-methylphenyl)-2-propanone

D

o-Tolyl-acetic acid 2-methyl-benzyl ester
80720-85-0

o-Tolyl-acetic acid 2-methyl-benzyl ester

Conditions
ConditionsYield
iron pentacarbonyl; tetrabutylammonium sulfate In sodium hydroxide; dichloromethane at 25℃; under 760 Torr; for 24h;A 69%
B 10%
C 7%
D 18%
iron pentacarbonyl; tetrabutylammonium sulfate In sodium hydroxide; dichloromethane at 25℃; under 760 Torr; for 24h;A 69%
B 10%
C 7%
D 18%
carbon monoxide
201230-82-2

carbon monoxide

2-methylbenzyl bromide
89-92-9

2-methylbenzyl bromide

A

o-xylene
95-47-6

o-xylene

B

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

C

1,2-bis(2-methylphenyl)ethane
952-80-7

1,2-bis(2-methylphenyl)ethane

D

1,3-bis(3,4-methylphenyl)acetone

1,3-bis(3,4-methylphenyl)acetone

Conditions
ConditionsYield
With sodium hydroxide; cobalt tricarbonyl nitrosyl; trimethyldodecylammonium chloride In benzene under 760 Torr; Ambient temperature;A 4%
B 68%
C 12%
D 10%
2-methylbenzyl bromide
89-92-9

2-methylbenzyl bromide

A

o-xylene
95-47-6

o-xylene

B

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

C

1,2-bis(2-methylphenyl)ethane
952-80-7

1,2-bis(2-methylphenyl)ethane

D

1,3-bis(3,4-methylphenyl)acetone

1,3-bis(3,4-methylphenyl)acetone

Conditions
ConditionsYield
With sodium hydroxide; cobalt tricarbonyl nitrosyl; carbon monoxide; trimethyldodecylammonium chloride In benzene under 760 Torr; Ambient temperature;A 4%
B 68%
C 12%
D 10%
carbon monoxide
201230-82-2

carbon monoxide

α,α-dibromo-o-xylene
79985-01-6

α,α-dibromo-o-xylene

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With potassium hydroxide; dicobalt octacarbonyl; N-benzyl-N,N,N-triethylammonium chloride In benzene under 760 Torr; for 12h; Ambient temperature;67%
carbon monoxide
201230-82-2

carbon monoxide

phthalyl alcohol
612-14-6

phthalyl alcohol

A

isochroman-3-one
4385-35-7

isochroman-3-one

B

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h;A 56%
B 9 % Spectr.
o-xylene
95-47-6

o-xylene

carbon dioxide
124-38-9

carbon dioxide

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With bis(2-pyridyl)methane; xanth-9-one; nickel(II) chloride hexahydrate; potassium tert-butylate In benzene at 20℃; under 760.051 Torr; for 4h; Reagent/catalyst; Irradiation; Schlenk technique;55%
1,1-dibromo-2-(2-methylphenyl)ethene
104464-03-1

1,1-dibromo-2-(2-methylphenyl)ethene

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With PEG-400; sodium hydroxide; bis[1,2-bis(diphenylphosphino)ethane]palladium(0) In dichloromethane at 60 - 65℃; for 17h;51%
Multi-step reaction with 2 steps
1: 99 percent / H2O / ethyl acetate / 12 h / 20 °C
2: 91 percent / aq. HCl / dioxane / 41 h / Heating
View Scheme
sodium cyanide
143-33-9

sodium cyanide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
Stage #1: sodium cyanide; 2-methylphenyl aldehyde With sodium disulfite In water
Stage #2: With hydrogenchloride at 20℃; for 12h;
38%
carbon monoxide
201230-82-2

carbon monoxide

2-methylbenzyl bromide
89-92-9

2-methylbenzyl bromide

A

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

B

o-Tolyl-acetic acid 2-methyl-benzyl ester
80720-85-0

o-Tolyl-acetic acid 2-methyl-benzyl ester

Conditions
ConditionsYield
With sodium hydroxide; η6-C6H6BPh3-Rh(COD)+; tetra-n-hexylammonium hydrogen sulfate In dichloromethane at 40℃; under 760 Torr;A 35%
B 20%
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

acetic acid
64-19-7

acetic acid

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With silver(I) acetate; sodium acetate; palladium dichloride at 130℃; for 24h; Schlenk technique; Inert atmosphere;18%
2-methylchlorobenzene
95-49-8

2-methylchlorobenzene

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With diethyl ether Eintragen einer Loesung des Reaktionsprodukts in Dioxan in eine warme Suspension von Silberoxid in Natriumthiosulfat enthaltender wss. Natriumcarbonat-Loesung;
1-methyl-2-(2-propenyl)-benzene
1587-04-8

1-methyl-2-(2-propenyl)-benzene

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With potassium permanganate; acetic acid at 0℃;
o-xylene
95-47-6

o-xylene

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With sodium; diethylmercury Durchleiten von Kohlendioxyd;
Multi-step reaction with 3 steps
1: bromine
2: alcohol
3: hydrogen peroxide; potassium hydroxide / Behandlung mit Salzsaeure
View Scheme
Multi-step reaction with 2 steps
1: dichloro[4,5-bis(diphenylphosphino)-9,9’-dimethylxanthene]palladium(II); di-tert-butyl peroxide / 16 h / 120 °C / 7600.51 Torr
2: water; sodium hydroxide / 1,4-dioxane / 2 h / 60 °C / pH 10 - 14
View Scheme
Multi-step reaction with 4 steps
1: chlorine / 4 h / 95 °C / Photolysis
2: iron(III) chloride; N-benzyl-N,N,N-triethylammonium chloride; boric acid / water / 1 h / 30 °C
3: sodium hydroxide / 6 h / 95 °C
4: hydrogenchloride; water / 20 °C
View Scheme
2-tolylmethylnitrile
22364-68-7

2-tolylmethylnitrile

A

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

B

2-methylphenethylamine
55755-16-3

2-methylphenethylamine

Conditions
ConditionsYield
With ethanol; sodium
homophthalic anhydride
703-59-3

homophthalic anhydride

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

Conditions
ConditionsYield
With hydrogen; palladium In ethyl acetate
methanol
67-56-1

methanol

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

methyl o-tolylacetate
40851-62-5

methyl o-tolylacetate

Conditions
ConditionsYield
With sulfuric acid at 0℃; for 8h; Reflux; Inert atmosphere;100%
With sulfuric acid for 6.5h; Inert atmosphere; Reflux;99%
With sulfuric acid at 28℃; for 12h;98%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

ethyl acrylate
140-88-5

ethyl acrylate

C14H16O4
1251864-79-5

C14H16O4

Conditions
ConditionsYield
With N-(tert-butyloxycarbonyl)-L-isoleucine; oxygen; palladium diacetate; p-benzoquinone In tert-Amyl alcohol at 85℃; under 760.051 Torr; for 48h; regioselective reaction;100%
With (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen; palladium diacetate; potassium hydrogencarbonate In tert-Amyl alcohol at 90℃; under 760.051 Torr; for 2h;97%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

C9H10O2*C12H23N

C9H10O2*C12H23N

Conditions
ConditionsYield
In methanol at 20℃;100%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

N-hydroxy-2-o-tolylacetamide
2594-02-7

N-hydroxy-2-o-tolylacetamide

Conditions
ConditionsYield
Stage #1: o-methylphenylacetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 1h;
Stage #2: With hydroxylamine hydrochloride In tetrahydrofuran; water for 16h;
99%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

C7H7BF3*K(1+)

C7H7BF3*K(1+)

2-(3,4'-dimethylbiphenyl-2-yl)acetic acid
1342343-93-4

2-(3,4'-dimethylbiphenyl-2-yl)acetic acid

Conditions
ConditionsYield
With palladium diacetate; potassium hydrogencarbonate; N-acetyl-L-isoleucine; silver carbonate; p-benzoquinone In tert-Amyl alcohol for 2h; Heating;99%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

O-(2,3-dimethylbut-2-enyl)hydroxylamine hydrochloride
1426580-46-2

O-(2,3-dimethylbut-2-enyl)hydroxylamine hydrochloride

N-(2,3-dimethylbut-2-enyloxy)-2-o-tolylacetamide
1426580-47-3

N-(2,3-dimethylbut-2-enyloxy)-2-o-tolylacetamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;99%
octanol
111-87-5

octanol

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

C17H26O2
1435489-74-9

C17H26O2

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 80℃; for 18h; Reagent/catalyst; Sealed tube;99%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

N-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-2-hydroxyacetamide

N-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-2-hydroxyacetamide

2-((3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)amino)-2-oxoethyl 2-(o-tolyl)acetate

2-((3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)amino)-2-oxoethyl 2-(o-tolyl)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;99%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

methyl o-tolylacetate
40851-62-5

methyl o-tolylacetate

Conditions
ConditionsYield
With sulfuric acid In methanol98%
With sulfuric acid In methanol98%
With sulfuric acid In formic acid for 6h; Reflux;
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

(1R,2R)-pseudoephedrine
321-97-1

(1R,2R)-pseudoephedrine

N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-2-o-tolylacetamide
1101876-22-5

N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-2-o-tolylacetamide

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;98%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

C6H4BF4*K(1+)

C6H4BF4*K(1+)

2-(4'-fluoro-3-methylbiphenyl-2-yl)acetic acid
1342343-98-9

2-(4'-fluoro-3-methylbiphenyl-2-yl)acetic acid

Conditions
ConditionsYield
With palladium diacetate; potassium hydrogencarbonate; N-acetyl-L-isoleucine; silver carbonate; p-benzoquinone In tert-Amyl alcohol for 2h; Heating;98%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

2-o-tolylethanol
19819-98-8

2-o-tolylethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether97%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Schlenk technique; Reflux;88%
With hydrogen In neat (no solvent) at 160℃; under 37503.8 Torr; for 24h;84%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

2-chloromethylphenylacetic acid
95335-46-9

2-chloromethylphenylacetic acid

chlorobenzene
108-90-7

chlorobenzene

phenylacetic acid
103-82-2

phenylacetic acid

Conditions
ConditionsYield
With sulfuryl dichloride96.8%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-methoxy-N-methyl-2-(2-methylphenyl)acetamide
918417-27-3

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

Conditions
ConditionsYield
Stage #1: o-methylphenylacetic acid; N,O-dimethylhydroxylamine*hydrochloride In chloroform for 0.166667h; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform for 0.166667h;
Stage #3: With triethylamine In chloroform for 3.16667h;
96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;94%
Stage #1: o-methylphenylacetic acid With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0℃; for 0.25h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 1h; chemoselective reaction;
80%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

ethyl acrylate
140-88-5

ethyl acrylate

(E)-2-(2-(3-ethoxy-3-oxoprop-1-en-1-yl)-6-methylphenyl)acetic acid
1215037-90-3

(E)-2-(2-(3-ethoxy-3-oxoprop-1-en-1-yl)-6-methylphenyl)acetic acid

Conditions
ConditionsYield
With (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen; palladium diacetate; potassium hydrogencarbonate In tert-Amyl alcohol at 90℃; under 760.051 Torr; for 2h; Kinetics; Mechanism; Reagent/catalyst;96%
With (S)-acetamidoalanine; palladium diacetate; potassium hydrogencarbonate In tert-Amyl alcohol at 90℃; for 2h;54%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

3-(o-tolyl)propanenitrile
26016-32-0

3-(o-tolyl)propanenitrile

Conditions
ConditionsYield
Stage #1: o-methylphenylacetic acid With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; iodine In chloroform at 60℃; Inert atmosphere;
Stage #2: trimethylsilyl cyanide With tetrabutyl ammonium fluoride In tetrahydrofuran; chloroform at 60℃; for 5h; Reagent/catalyst; Inert atmosphere; chemoselective reaction;
96%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

C14H18O3

C14H18O3

Conditions
ConditionsYield
With β-cyclodextrin-SO3H In neat (no solvent) at 70℃; for 3h;96%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

o-Tolylacetic acid 4-nitro-benzyl ester
866785-40-2

o-Tolylacetic acid 4-nitro-benzyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 50℃; for 20h;95%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

C6H4BClF3*K(1+)

C6H4BClF3*K(1+)

2-(4'-chloro-3-methyl-[1,1'-biphenyl]-2-yl)acetic acid
1342343-95-6

2-(4'-chloro-3-methyl-[1,1'-biphenyl]-2-yl)acetic acid

Conditions
ConditionsYield
With palladium diacetate; potassium hydrogencarbonate; N-acetyl-L-isoleucine; silver carbonate; p-benzoquinone In tert-Amyl alcohol for 2h; Heating;95%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

2-(4-methyl-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-3-yl)acetic acid

2-(4-methyl-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-3-yl)acetic acid

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate; (3r,5r,7r)-N-(2-hydroxy-5-(trifluoromethyl)pyridin-3-yl)adamantane-1-carboxamide; palladium diacetate; silver carbonate at 100℃; for 24h;95%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

2-(1-cyclohexenyl)ethylamine
3399-73-3

2-(1-cyclohexenyl)ethylamine

N-[2-(cyclohex-1-en-1-yl)ethyl]-2-(o-tolyl)acetamide

N-[2-(cyclohex-1-en-1-yl)ethyl]-2-(o-tolyl)acetamide

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;95%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

propargyl alcohol
107-19-7

propargyl alcohol

C12H12O2
90705-93-4

C12H12O2

Conditions
ConditionsYield
With β-cyclodextrin-SO3H In neat (no solvent) at 70℃; for 4h;94%
With toluene-4-sulfonic acid at 80℃;
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

3,5-dimethylphenyl iodide
22445-41-6

3,5-dimethylphenyl iodide

2-(3',4,5'-trimethyl-[1,1'-biphenyl]-3-yl)acetic acid

2-(3',4,5'-trimethyl-[1,1'-biphenyl]-3-yl)acetic acid

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate; (3r,5r,7r)-N-(2-hydroxy-5-(trifluoromethyl)pyridin-3-yl)adamantane-1-carboxamide; palladium diacetate; silver carbonate at 100℃; for 24h;94%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

methyl iodide
74-88-4

methyl iodide

methyl 2-[2-(bromomethyl)phenyl]acetate
13737-37-6

methyl 2-[2-(bromomethyl)phenyl]acetate

Conditions
ConditionsYield
Stage #1: o-methylphenylacetic acid; methyl iodide With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 12h;
Stage #2: With N-Bromosuccinimide In acetonitrile at 80℃; for 2h;
94%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

methyl iodide
74-88-4

methyl iodide

(rac)-2-(2-methylphenyl)propanoic acid
137144-15-1, 144789-13-9, 62835-95-4

(rac)-2-(2-methylphenyl)propanoic acid

Conditions
ConditionsYield
Stage #1: o-methylphenylacetic acid With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
93%
Stage #1: o-methylphenylacetic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
82%
Stage #1: o-methylphenylacetic acid With n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
59%

644-36-0Relevant articles and documents

HOMOGENEOUS AND PHASE TRANSFER CATALYZED CARBONYLATION REACTIONS

Alper, Howard

, p. 1 - 6 (1986)

-

Alkali-modified heterogeneous Pd-catalyzed synthesis of acids, amides and esters from aryl halides using formic acid as the CO precursor

Fapojuwo, Dele Peter,Maqunga, Nomathamsanqa Prudence,Meijboom, Reinout,Mogudi, Batsile M.,Molokoane, Pule Petrus,Onisuru, Oluwatayo Racheal,Oseghale, Charles O.

, p. 26937 - 26948 (2021/08/17)

To establish an environmentally friendly green chemical process, we minimized and resolved a significant proportion of waste and hazards associated with conventional organic acids and molecular gases, such as carbon monoxide (CO). Herein, we report a facile and milder reaction procedure, using low temperatures/pressures and shorter reaction time for the carboxyl- and carbonylation of diverse arrays of aryl halides over a newly developed cationic Lewis-acid promoted Pd/Co3O4catalyst. Furthermore, the reaction proceeded in the absence of acid co-catalysts, and anhydrides for CO release. Catalyst reusability was achievedviascalable, safer, and practical reactions that provided moderate to high yields, paving the way for developing a novel environmentally benign method for synthesizing carboxylic acids, amides, and esters.

Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide

Wakuluk-Machado, Anne-Marie,Dewez, Damien F.,Baguia, Hajar,Imbratta, Miguel,Echeverria, Pierre-Georges,Evano, Gwilherm

, p. 713 - 723 (2020/02/04)

A simple, efficient, cheap, and broadly applicable system for the carboxylation of benzylic bromides with carbon monoxide and water is reported. Upon simple reaction with only 2.5 wt % of Pearlman's catalyst and 10 mol % of tetrabutylammonium bromide in tetrahydrofuran at 110 °C for 4 h, a range of benzylic bromides can be smoothly converted to the corresponding arylacetic acids in good to excellent yields after simple extraction and acid-base wash. The reaction was found to be broadly applicable, scalable, and could be successfully extended to the use of ex situ-generated carbon monoxide and applied to the synthesis of the nonsteroidal anti-inflammatory drug diclofenac.

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