methanol
2-benzofuran-1(3H)-one
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
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
2-(chloromethyl)benzoic acid
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid at 80℃; for 6h; Temperature; | 96.5% |
2-Chloromethylbenzoyl chloride
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
In methanol | 94% |
With triethylamine In methanol; dichloromethane | 89% |
2-Methyl-benzoic acid methyl ester
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
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
A
o-(chloromethyl)benzoic acid methyl ester
B
3-hydroxy-benzeneacetic acid, methyl ester
C
methyl 3-hydroxy-4-<2-(methoxycarbonyl)benzyl>phenylacetate
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane for 0.666667h; Ambient temperature; | A 30.9% B 55.2% C 28.7% |
methanol
2-Chloromethylbenzoyl chloride
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
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
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
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
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride 2: methanol View Scheme |
ortho-methylbenzoic acid
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
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
2,3-Dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 80℃; for 5h; | 100% |
o-(chloromethyl)benzoic acid methyl ester
cyclohexylamine
2-cyclohexyl-2,3-dihydro-1H-isoindol-1-one
Conditions | Yield |
---|---|
In neat (no solvent) at 140℃; for 2h; | 98% |
o-(chloromethyl)benzoic acid methyl ester
aniline
N-phenylphthalimidine
Conditions | Yield |
---|---|
In neat (no solvent) at 140℃; for 2h; | 98% |
o-(chloromethyl)benzoic acid methyl ester
Methyl 4-hydroxyphenylacetate
4-(2-methoxycarbonylbenzyloxy)phenyl acetic acid
Conditions | Yield |
---|---|
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
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.666667h; Reflux; | 92% |
o-(chloromethyl)benzoic acid methyl ester
4-chloro-2-mercaptobenzonitrile
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.666667h; Reflux; | 86% |
o-(chloromethyl)benzoic acid methyl ester
4,6-diphenyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.5h; Reflux; | 86% |
methanol
o-(chloromethyl)benzoic acid methyl ester
methyl 2-(methoxymethyl)benzoate
Conditions | Yield |
---|---|
With sodium hydride for 4h; Heating; | 85% |
o-(chloromethyl)benzoic acid methyl ester
2-cyanothiophenol
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.666667h; Reflux; | 84% |
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.5h; Reflux; | 84% |
o-(chloromethyl)benzoic acid methyl ester
2-(Chlorosulfonylmethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
With Sodium thiosulfate pentahydrate; chlorine; acetic acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water | 83% |
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
o-(2-ethoxycarbonyl)phenylmethanesulfonyl chloride
Conditions | Yield |
---|---|
With Sodium thiosulfate pentahydrate | 81% |
o-(chloromethyl)benzoic acid methyl ester
methyl 2-(chloromethyl)-5-nitrobenzoate
Conditions | Yield |
---|---|
With sulfuric acid; potassium nitrate at 0 - 20℃; for 4h; | 80% |
o-(chloromethyl)benzoic acid methyl ester
1,2,5,6,7,8-hexahydro-2-thioxoquinoline-3-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.5h; Reflux; | 78% |
o-(chloromethyl)benzoic acid methyl ester
2-Fluorobenzaldehyde
3-(2-fluorophenyl)-3,4-dihydroisocoumarin
Conditions | Yield |
---|---|
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
4-phenyl-6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.5h; Reflux; | 76% |
o-(chloromethyl)benzoic acid methyl ester
4-fluorobenzaldehyde
Conditions | Yield |
---|---|
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
4,6-Dimethyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.5h; Reflux; | 74% |
o-(chloromethyl)benzoic acid methyl ester
2-thioxo-6-phenyl-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.5h; Reflux; | 74% |
o-(chloromethyl)benzoic acid methyl ester
1-cyano-2-hydroxynaphthalene
C20H15NO3
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h; | 72% |
m-bromobenzoic aldehyde
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
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
allyltrimethoxysilane
Conditions | Yield |
---|---|
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
o-(chloromethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
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
5-chloro-2-hydroxybenzonitrile
C16H12ClNO3
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h; | 67% |
o-(chloromethyl)benzoic acid methyl ester
2-cyano-4-methylphenol
C17H15NO3
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h; | 65% |
o-(chloromethyl)benzoic acid methyl ester
benzaldehyde
3-phenyl-isochroman-1-one
Conditions | Yield |
---|---|
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
o-(chloromethyl)benzoic acid methyl ester
methyl 2-[(2-cyanobenzyl)oxy]benzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h; | 62% |
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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