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612-13-5

Basic Information
CAS No.: 612-13-5
Name: Benzonitrile,2-(chloromethyl)-
Article Data: 10
Cas Database
Molecular Structure:
Molecular Structure of 612-13-5 (Benzonitrile,2-(chloromethyl)-)
Formula: C8H6ClN
Molecular Weight: 151.595
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;
EINECS: 210-292-3
Density: 1.18 g/cm3
Melting Point: 56-61 °C
Boiling Point: 252 °C at 760 mmHg
Flash Point: 106.2 °C
Solubility: N/A
Appearance: white to light yellow crystal powder
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 23.79000
LogP: 2.29708
Synthetic route
529-19-1

2-Methylbenzonitrile

612-13-5

2-cyanobenzyl chloride

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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    612-13-5 CAS NO.612-13-5

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  • 2-Cyanobenzylchloride

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    2-Cyanobenzylchloride

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    612-13-5

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  • 2-(Chloromethyl)benzonitrile CAS 612-13-5

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    2-(Chloromethyl)benzonitrile

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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,