Product Name

  • Name

    Methyl 2-chloromethylbenzoate

  • EINECS 251-805-0
  • CAS No. 34040-62-5
  • Article Data11
  • CAS DataBase
  • Density 1.19 g/cm3
  • Solubility
  • Melting Point
  • Formula C9H9ClO2
  • Boiling Point 282 °C at 760 mmHg
  • Molecular Weight 184.622
  • Flash Point 139.2 °C
  • Transport Information
  • Appearance COA
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 34040-62-5 (Methyl 2-chloromethylbenzoate)
  • Hazard Symbols
  • Synonyms o-Toluicacid, a-chloro-, methyl ester (8CI);2-(Chloromethyl)benzoic acid methyl ester;Methyl o-(chloromethyl)benzoate;
  • PSA 26.30000
  • LogP 2.21200

Synthetic route

methanol
67-56-1

methanol

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 2-benzofuran-1(3H)-one With boron trifluoride diethyl etherate; N-benzyl-N,N,N-triethylammonium chloride In xylene at 100℃;
Stage #2: With thionyl chloride In xylene at 100 - 132℃; for 3h;
Stage #3: methanol at 50 - 60℃; for 2h;		100%
Stage #1: 2-benzofuran-1(3H)-one With dichlorotriphenyl-λ4-phosphane at 180℃; for 2h;
Stage #2: methanol With pyridine for 1h;
With pyridine; dichlorotriphenylphosphorane at 180℃;
methanol
67-56-1

methanol

2-(chloromethyl)benzoic acid
85888-81-9

2-(chloromethyl)benzoic acid

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 6h; Temperature;96.5%
2-Chloromethylbenzoyl chloride
42908-86-1

2-Chloromethylbenzoyl chloride

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Conditions
ConditionsYield
In methanol94%
With triethylamine In methanol; dichloromethane89%
2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Conditions
ConditionsYield
With N-hydroxyphthalimide; carbon tetrabromide; trichloroisocyanuric acid; copper(II) acetate monohydrate In dichloromethane at 25℃; for 24h;61%
With N-hydroxyphthalimide; carbon tetrabromide; trichloroisocyanuric acid; copper(II) acetate monohydrate In dichloromethane at 25℃; for 20h;49%
methyl 3-<2-(methoxycarbonyl)benzyloxy>phenylacetate
93273-66-6

methyl 3-<2-(methoxycarbonyl)benzyloxy>phenylacetate

A

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

B

3-hydroxy-benzeneacetic acid, methyl ester
42058-59-3

3-hydroxy-benzeneacetic acid, methyl ester

C

methyl 3-hydroxy-4-<2-(methoxycarbonyl)benzyl>phenylacetate
93273-67-7

methyl 3-hydroxy-4-<2-(methoxycarbonyl)benzyl>phenylacetate

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane for 0.666667h; Ambient temperature;A 30.9%
B 55.2%
C 28.7%
...Expand
methanol
67-56-1

methanol

2-Chloromethylbenzoyl chloride
42908-86-1

2-Chloromethylbenzoyl chloride

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Conditions
ConditionsYield
With pyridine for 18h; Yield given;
for 3h; Heating;1000 mg
Stage #1: methanol; 2-Chloromethylbenzoyl chloride at 50 - 60℃; for 2h;
Stage #2: With potassium carbonate In water; toluene for 0.5h;
3-(2-carboxybenzyloxy)phenylacetic acid
55690-19-2

3-(2-carboxybenzyloxy)phenylacetic acid

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95.3 percent / conc. H2SO4 / 22 h / Heating
2: 30.9 percent / aluminium chloride / 1,2-dichloro-ethane / 0.67 h / Ambient temperature
View Scheme
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride
2: methanol
View Scheme
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,2'-azobis(isobutyronitrile); thionyl chloride / 1,2-dichloro-ethane / 4 h / 60 °C
2: sulfuric acid / 6 h / 80 °C
View Scheme
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

2,3-Dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester
161468-45-7

2,3-Dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester

tert-butyl 3-(2-(methoxycarbonyl)benzyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate

tert-butyl 3-(2-(methoxycarbonyl)benzyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 5h;100%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

cyclohexylamine
108-91-8

cyclohexylamine

2-cyclohexyl-2,3-dihydro-1H-isoindol-1-one
3823-13-0

2-cyclohexyl-2,3-dihydro-1H-isoindol-1-one

Conditions
ConditionsYield
In neat (no solvent) at 140℃; for 2h;98%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

aniline
62-53-3

aniline

N-phenylphthalimidine
5388-42-1

N-phenylphthalimidine

Conditions
ConditionsYield
In neat (no solvent) at 140℃; for 2h;98%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Methyl 4-hydroxyphenylacetate
14199-15-6

Methyl 4-hydroxyphenylacetate

4-(2-methoxycarbonylbenzyloxy)phenyl acetic acid
1009378-92-0

4-(2-methoxycarbonylbenzyloxy)phenyl acetic acid

Conditions
ConditionsYield
With potassium carbonate In ethanol for 24h; Reagent/catalyst; Reflux;96.9%
With potassium carbonate In ISOPROPYLAMIDE at 90℃; for 8h;
With potassium carbonate In ISOPROPYLAMIDE at 90℃; for 8h;
2-mercapto-4-methylbenzonitrile
613263-26-6

2-mercapto-4-methylbenzonitrile

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

methyl 2-{[(2-cyano-5-methylphenyl)thio]methyl}benzoate

methyl 2-{[(2-cyano-5-methylphenyl)thio]methyl}benzoate

Conditions
ConditionsYield
With triethylamine In chloroform for 0.666667h; Reflux;92%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

4-chloro-2-mercaptobenzonitrile
1339650-77-9

4-chloro-2-mercaptobenzonitrile

methyl 2-{[(5-chloro-2-cyanophenyl)thio]methyl}benzoate

methyl 2-{[(5-chloro-2-cyanophenyl)thio]methyl}benzoate

Conditions
ConditionsYield
With triethylamine In chloroform for 0.666667h; Reflux;86%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

4,6-diphenyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile
58327-74-5

4,6-diphenyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile

3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-4,6-diphenylpyridine

3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-4,6-diphenylpyridine

Conditions
ConditionsYield
With triethylamine In chloroform for 0.5h; Reflux;86%
methanol
67-56-1

methanol

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

methyl 2-(methoxymethyl)benzoate
942-57-4

methyl 2-(methoxymethyl)benzoate

Conditions
ConditionsYield
With sodium hydride for 4h; Heating;85%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

2-cyanothiophenol
34761-11-0

2-cyanothiophenol

methyl 2-{[(2-cyanophenyl)thio]methyl}benzoate

methyl 2-{[(2-cyanophenyl)thio]methyl}benzoate

Conditions
ConditionsYield
With triethylamine In chloroform for 0.666667h; Reflux;84%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

6-(4-bromophenyl)-3-cyano-4-phenylpyridine-2(1H)-thione

6-(4-bromophenyl)-3-cyano-4-phenylpyridine-2(1H)-thione

6-(4-bromophenyl)-3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-4-phenylpyridine

6-(4-bromophenyl)-3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-4-phenylpyridine

Conditions
ConditionsYield
With triethylamine In chloroform for 0.5h; Reflux;84%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

2-(Chlorosulfonylmethyl)benzoic acid methyl ester
103342-27-4

2-(Chlorosulfonylmethyl)benzoic acid methyl ester

Conditions
ConditionsYield
With Sodium thiosulfate pentahydrate; chlorine; acetic acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water83%
Multi-step reaction with 2 steps
1: sodium thiosulfate / water / 3 h / 70 °C
2: water; chlorine / 1,2-dichloro-benzene / 5 h / 10 - 30 °C
View Scheme
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

o-(2-ethoxycarbonyl)phenylmethanesulfonyl chloride
221631-54-5

o-(2-ethoxycarbonyl)phenylmethanesulfonyl chloride

Conditions
ConditionsYield
With Sodium thiosulfate pentahydrate81%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

methyl 2-(chloromethyl)-5-nitrobenzoate
90537-42-1

methyl 2-(chloromethyl)-5-nitrobenzoate

Conditions
ConditionsYield
With sulfuric acid; potassium nitrate at 0 - 20℃; for 4h;80%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

1,2,5,6,7,8-hexahydro-2-thioxoquinoline-3-carbonitrile
112629-69-3

1,2,5,6,7,8-hexahydro-2-thioxoquinoline-3-carbonitrile

3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-5,6,7,8-tetrahydroquinoline

3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-5,6,7,8-tetrahydroquinoline

Conditions
ConditionsYield
With triethylamine In chloroform for 0.5h; Reflux;78%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

3-(2-fluorophenyl)-3,4-dihydroisocoumarin
95217-42-8

3-(2-fluorophenyl)-3,4-dihydroisocoumarin

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; for 16h; Glovebox; Inert atmosphere;77%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

4-phenyl-6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile
82127-11-5

4-phenyl-6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile

3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-4-phenyl-6-(2-thienyl)pyridine

3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-4-phenyl-6-(2-thienyl)pyridine

Conditions
ConditionsYield
With triethylamine In chloroform for 0.5h; Reflux;76%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

3,4-dihydro-3-(4'-fluorophenyl)isocoumarine

3,4-dihydro-3-(4'-fluorophenyl)isocoumarine

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; for 16h; Glovebox; Inert atmosphere;75%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

4,6-Dimethyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile
54585-47-6

4,6-Dimethyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile

3-cyano-4,6-dimethyl-2-{[2-(methoxycarbonyl)benzyl]thio}pyridine

3-cyano-4,6-dimethyl-2-{[2-(methoxycarbonyl)benzyl]thio}pyridine

Conditions
ConditionsYield
With triethylamine In chloroform for 0.5h; Reflux;74%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

2-thioxo-6-phenyl-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile
104960-49-8

2-thioxo-6-phenyl-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-6-phenyl-4-(trifluoromethyl)pyridine

3-cyano-2-{[2-(methoxycarbonyl)benzyl]thio}-6-phenyl-4-(trifluoromethyl)pyridine

Conditions
ConditionsYield
With triethylamine In chloroform for 0.5h; Reflux;74%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

1-cyano-2-hydroxynaphthalene
52805-47-7

1-cyano-2-hydroxynaphthalene

C20H15NO3
1293961-06-4

C20H15NO3

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h;72%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

(dl)-3-(3'-bromophenyl)-3,4-dihydroisocoumarin

(dl)-3-(3'-bromophenyl)-3,4-dihydroisocoumarin

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; for 16h; Glovebox; Inert atmosphere;71%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

allyltrimethoxysilane
2551-83-9

allyltrimethoxysilane

methyl 5-allyl-2-methylbenzoate

methyl 5-allyl-2-methylbenzoate

Conditions
ConditionsYield
Stage #1: o-(chloromethyl)benzoic acid methyl ester; allyltrimethoxysilane With tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 12h; Hiyama Coupling; Inert atmosphere;
Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran; dichloromethane at 20℃; for 0.166667h; Inert atmosphere; regioselective reaction;		70%
4-Trifluoromethylbenzaldehyde
455-19-6

4-Trifluoromethylbenzaldehyde

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

3-(4-(trifluoromethyl)phenyl)-3,4-dihydroisocoumarin

3-(4-(trifluoromethyl)phenyl)-3,4-dihydroisocoumarin

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; for 16h; Glovebox; Inert atmosphere;68%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

5-chloro-2-hydroxybenzonitrile
13589-72-5

5-chloro-2-hydroxybenzonitrile

C16H12ClNO3
1293960-94-7

C16H12ClNO3

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h;67%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

2-cyano-4-methylphenol
51282-90-7

2-cyano-4-methylphenol

C17H15NO3
1293960-91-4

C17H15NO3

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h;65%
o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

benzaldehyde
100-52-7

benzaldehyde

3-phenyl-isochroman-1-one
2674-44-4, 146518-60-7

3-phenyl-isochroman-1-one

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; for 16h; Reagent/catalyst; Solvent; Temperature; Glovebox; Inert atmosphere;64%
salicylonitrile
611-20-1

salicylonitrile

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

methyl 2-[(2-cyanobenzyl)oxy]benzoate
1293960-89-0

methyl 2-[(2-cyanobenzyl)oxy]benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h;62%

Methyl 2-chloromethylbenzoate Specification

The Methyl 2-chloromethylbenzoate, with the CAS registry number 34040-62-5 and EINECS registry number 251-805-0, has the systematic name and IUPAC name of methyl 2-(chloromethyl)benzoate. It belongs to the product category of Aromatic Esters. And the molecular formula of the chemical is C9H9ClO2.

The characteristics of Methyl 2-chloromethylbenzoate are as followings: (1)ACD/LogP: 2.47; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.46; (4)ACD/LogD (pH 7.4): 2.46; (5)ACD/BCF (pH 5.5): 43.96; (6)ACD/BCF (pH 7.4): 43.96; (7)ACD/KOC (pH 5.5): 522.06; (8)ACD/KOC (pH 7.4): 522.06; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.528; (14)Molar Refractivity: 47.79 cm3; (15)Molar Volume: 155 cm3; (16)Polarizability: 18.94×10-24cm3; (17)Surface Tension: 38.9 dyne/cm; (18)Density: 1.19 g/cm3; (19)Flash Point: 139.2 °C; (20)Enthalpy of Vaporization: 52.09 kJ/mol; (21)Boiling Point: 282 °C at 760 mmHg; (22)Vapour Pressure: 0.00344 mmHg at 25°C. 

Uses of Methyl 2-chloromethylbenzoate: It can react with methanol to produce 2-methoxymethyl-benzoic acid methyl ester. This reaction will need reagent NaH. The reaction time is 4 hours with heating, and the yield is about 85%.    

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: ClCc1ccccc1C(=O)OC
(2)InChI: InChI=1/C9H9ClO2/c1-12-9(11)8-5-3-2-4-7(8)6-10/h2-5H,6H2,1H3
(3)InChIKey: AAHZCIWUDPKSJP-UHFFFAOYAB

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