2-(Chloromethyl)benzonitrile supplier

Name
2-(Chloromethyl)benzonitrile
EINECS 210-292-3
CAS No. 612-13-5
Article Data10
CAS DataBase
Density 1.18 g/cm³
Solubility
Melting Point 56-61 °C
Formula C₈H₆ClN
Boiling Point 252 °C at 760 mmHg
Molecular Weight 151.595
Flash Point 106.2 °C
Transport Information
Appearance white to light yellow crystal powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms o-Tolunitrile,a-chloro- (6CI,7CI,8CI);a-Tolunitrile, a-chloro- (3CI);2-(Chloromethyl)benzonitrile;2-Cyanobenzyl chloride;NSC 102157;o-(Chloromethyl)benzonitrile;o-Cyanobenzylchloride;a-Chloro-o-toluonitrile;
PSA 23.79000
LogP 2.29708

Synthetic route

: 529-19-1
2-Methylbenzonitrile

: 612-13-5
2-cyanobenzyl chloride

Conditions

Conditions	Yield
With tert-butylhypochlorite; bis(1,10-phenanthroline)silver(I) triflate In acetonitrile at 20℃; for 48h; Inert atmosphere; regioselective reaction;	42%
Stage #1: 2-Methylbenzonitrile With fluorosulphonic acid; lead dioxide at -75℃; for 5h; Stage #2: With hydrogenchloride	29%
With chlorine

: 2-cyanobenzylselenocyanate

A: 92380-62-6
2-selanylmethyl-benzonitrile; hydrochloride

B: 612-13-5
2-cyanobenzyl chloride

Conditions

Conditions	Yield
With hydrogenchloride at 100℃; im geschlossenen Rohr;

: 529-19-1
2-Methylbenzonitrile

: 7782-50-5
chlorine

: 612-13-5
2-cyanobenzyl chloride

: 118-90-1
ortho-methylbenzoic acid

: 612-13-5
2-cyanobenzyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / Pb(SCN)2 / 200 - 230 °C 2: 1.) PbO2, HSO3F, 2.) aq. HCl / multistep reaction; various temperatures, reaction time, reagent ratios View Scheme

: 98-54-4
para-tert-butylphenol

: 612-13-5
2-cyanobenzyl chloride

: 2-(4-tert-butylphenoxymethyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	99.8%

: 108-39-4
3-methyl-phenol

: 612-13-5
2-cyanobenzyl chloride

: 951906-95-9
2-(3-methylphenoxymethyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	99.3%

: 95-48-7
ortho-cresol

: 612-13-5
2-cyanobenzyl chloride

: 951906-92-6
2-(2-methylphenoxymethyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	99.3%

: 100-02-7
4-nitro-phenol

: 612-13-5
2-cyanobenzyl chloride

: 1004433-16-2
2-((4-nitrophenoxy)methyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	99.2%

: 106-48-9
4-chloro-phenol

: 612-13-5
2-cyanobenzyl chloride

: 92161-45-0
2-(4-chlorophenoxymethyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	99%

: 4394-85-8
4-morpholinecarboxaldehyde

: 612-13-5
2-cyanobenzyl chloride

: 37812-33-2
2-(morpholin-4-ylmethyl)benzonitrile

Conditions

Conditions	Yield
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;	99%
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;	98%

: 612-13-5
2-cyanobenzyl chloride

: 108-95-2
phenol

: 168971-54-8
2-(phenoxymethyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	98.2%
With ethanol; sodium

: 105-67-9
2,4-Xylenol

: 612-13-5
2-cyanobenzyl chloride

: 951905-98-9
2-(2,4-dimethylphenoxymethyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	96.5%

: 67-56-1
methanol

: 612-13-5
2-cyanobenzyl chloride

: 2-Chloromethyl-benzimidic acid methyl ester; hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether at 0 - 5℃; for 6h;	96%

: 536-74-3
phenylacetylene

: 612-13-5
2-cyanobenzyl chloride

: 1-(2-cyanobenzyl)-4-phenyl-1H-1,2,3-triazole

Conditions

Conditions	Yield
With sodium azide; sodium L-ascorbate In water at 60℃; for 3.5h;	96%

: 97210-23-6
(±)-1-(4-chlorophenyl)-2-(1H-pyrrol-1-yl)ethanol

: 612-13-5
2-cyanobenzyl chloride

: 2-[1-(4-Chloro-phenyl)-2-pyrrol-1-yl-ethoxymethyl]-benzonitrile; hydrochloride

Conditions

Conditions	Yield
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide 25 deg C, 1 h; 50 deg C, 1 h;	95%

: 90-05-1
2-methoxy-phenol

: 612-13-5
2-cyanobenzyl chloride

: 951907-13-4
2-(2-methoxyphenoxymethyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	95%

: 135-19-3
β-naphthol

: 612-13-5
2-cyanobenzyl chloride

: 2-[(naphthalen-2-yloxy)methyl]benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	94.6%

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: 612-13-5
2-cyanobenzyl chloride

: 787562-31-6
2-{[(4-methyl-2-coumarin-7-yl)oxy]methyl}benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	94.3%

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

: 612-13-5
2-cyanobenzyl chloride

: 1293961-08-6
C19H12N2O

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h;	93%

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

: 612-13-5
2-cyanobenzyl chloride

: 3-cyano-2-(2-cyanobenzylthio)-4,6-dimethylpyridine

Conditions

Conditions	Yield
With triethylamine In chloroform for 0.666667h; Reflux;	93%

: 612-13-5
2-cyanobenzyl chloride

: 57991-54-5
2-(methoxymethyl)benzonitrile

Conditions

Conditions	Yield
With sodium methylate In methanol at 25℃; for 4h;	93%

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

: 612-13-5
2-cyanobenzyl chloride

: 1293960-99-2
C16H12N2O

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h;	92%

: 613263-26-6
2-mercapto-4-methylbenzonitrile

: 612-13-5
2-cyanobenzyl chloride

: 2-[(2-cyanobenzyl)thio]-5-methylbenzonitrile

Conditions

Conditions	Yield
With triethylamine In chloroform for 0.666667h; Reflux;	92%

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

: 612-13-5
2-cyanobenzyl chloride

: 3-cyano-2-(2-cyanobenzylthio)-5,6,7,8-tetrahydroquinoline

Conditions

Conditions	Yield
With triethylamine In chloroform for 0.666667h; Reflux;	92%

: 59089-68-8
4-(2,4-difluorophenyl)-phenol

: 612-13-5
2-cyanobenzyl chloride

: 1417422-68-4
2-[4-(2,4-difluorophenyl)phenoxymethyl]benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	91.5%

: (1-((diphenylmethylene)amino)-2-morpholino-2-oxoethyl)zinc pivalate

: 612-13-5
2-cyanobenzyl chloride

: 2-(2-((diphenylmethylene)amino)-3-morpholino-3-oxopropyl)benzonitrile

Conditions

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0); DavePhos In tetrahydrofuran at 25℃; for 4h; Negishi Coupling; Inert atmosphere;	91%

: 90-15-3
α-naphthol

: 612-13-5
2-cyanobenzyl chloride

: 1004489-90-0
2-(1-naphthoxymethyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	90.4%

: 612-13-5
2-cyanobenzyl chloride

: 98-80-6
phenylboronic acid

: 56153-61-8
2-benzyl-benzonitrile

Conditions

Conditions	Yield
With potassium phosphate tribasic trihydrate In ethanol at 80℃; for 1h; Catalytic behavior; Suzuki-Miyaura Coupling;	90%
With potassium carbonate; sodium chloride; palladium dichloride; cucurbituril In ethanol; water at 90℃; for 1h; Suzuki Coupling; Inert atmosphere;	88%
With potassium carbonate; N,N-dimethyl-formamide; palladium dichloride In water at 90℃; for 1h; Suzuki Coupling;	88%

: 576-26-1
2.6-dimethylphenol

: 612-13-5
2-cyanobenzyl chloride

: 951905-86-5
2-(2,6-dimethylphenoxymethyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	89.4%

: 121-33-5
vanillin

: 612-13-5
2-cyanobenzyl chloride

: 443289-08-5
2-((4-formyl-2-methoxyphenoxy)methyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	88.2%
With potassium carbonate In acetonitrile Reflux;
With potassium carbonate In acetonitrile Reflux;

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

: 612-13-5
2-cyanobenzyl chloride

: 1293961-01-9
C15H9ClN2O

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h;	86%

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

: 612-13-5
2-cyanobenzyl chloride

: 5-chloro-2-[(2-cyanobenzyl)thio]benzonitrile

Conditions

Conditions	Yield
With triethylamine In chloroform for 0.666667h; Reflux;	86%

: 4318-56-3
3-methyl-6-chlorouracil

: 612-13-5
2-cyanobenzyl chloride

: 865758-96-9
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 60℃; for 1h;	85.62%
With potassium carbonate; potassium iodide In N,N-dimethyl acetamide at 50 - 100℃;

: 611-20-1
salicylonitrile

: 612-13-5
2-cyanobenzyl chloride

: 1002241-42-0
2-[(2-cyanobenzyl)oxy]benzonitril

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h;	84%

2-(Chloromethyl)benzonitrile Specification

The o-Cyanobenzylchloride, with the cas registry number 612-13-5, has the IUPAC name of 2-(chloromethyl)benzonitrile. It is a kind of white to light yellow crystal powder with pungent smell. And it is soluble in ethanol, chloroform, acetone, toluene and othe orgainc solvent. Besides, its product categories are including intermediates of dyes and pigments.

The characteristics of this chemical are as follows: (1)ACD/LogP: 1.92; (2)ACD/LogD (pH 5.5): 1.92; (3)ACD/LogD (pH 7.4): 1.92; (4)ACD/BCF (pH 5.5): 17.06; (5)ACD/BCF (pH 7.4): 17.06; (6)ACD/KOC (pH 5.5): 265.11; (7)ACD/KOC (pH 7.4): 265.11; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 23.79; (11)Index of Refraction: 1.551; (12)Molar Refractivity: 40.77 cm³; (13)Molar Volume: 127.8 cm³; (14)Polarizability: 16.16 ×10^-24 cm³; (15)Surface Tension: 44.5 dyne/cm; (16)Density: 1.18 g/cm³; (17)Flash Point: 106.2 °C; (18)Enthalpy of Vaporization: 48.93 kJ/mol; (19)Boiling Point: 252 °C at 760 mmHg; (20)Vapour Pressure: 0.0198 mmHg at 25°C; (21)Exact Mass: 151.018877; (22)MonoIsotopic Mass: 151.018877; (23)Topological Polar Surface Area: 23.8; (24)Heavy Atom Count: 10; (25)Formal Charge: 0; (26)Complexity: 147.

Use of o-cyanobenzylchloride: o-cyanobenzylchloride could react with methanol to produce 2-chloromethyl-benzimidic acid methyl ester; hydrochloride, with the following condition: reagent: HCl; solvent: diethyl ether; reaction time: 6 hours; reaction temp.: 0 - 5 ℃; yield: 96%.

As to its usage, it is widely applied in many ways. It could be used as the organic synthesis intermediate; It could also be used as synthetize the distyryl benzene fluorescent brighteners, such as brightener ER.

In addition, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: C1=CC=C(C(=C1)CCl)C#N
(2)InChI: InChI=1S/C8H6ClN/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5H2
(3)InChIKey: ZSHNOXOGXHXLAV-UHFFFAOYSA-N

Below are the toxicity information of this chemical:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	56mg/kg (56mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02570,

Product Name

2-(Chloromethyl)benzonitrile

Synthetic route

2-(Chloromethyl)benzonitrile Specification

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