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 |
A
2-selanylmethyl-benzonitrile; hydrochloride
B
2-cyanobenzyl chloride
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; im geschlossenen Rohr; |
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 |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 99.8% |
3-methyl-phenol
2-cyanobenzyl chloride
2-(3-methylphenoxymethyl)benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 99.3% |
ortho-cresol
2-cyanobenzyl chloride
2-(2-methylphenoxymethyl)benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 99.3% |
4-nitro-phenol
2-cyanobenzyl chloride
2-((4-nitrophenoxy)methyl)benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 99.2% |
4-chloro-phenol
2-cyanobenzyl chloride
2-(4-chlorophenoxymethyl)benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 99% |
4-morpholinecarboxaldehyde
2-cyanobenzyl chloride
2-(morpholin-4-ylmethyl)benzonitrile
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% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 98.2% |
With ethanol; sodium |
2,4-Xylenol
2-cyanobenzyl chloride
2-(2,4-dimethylphenoxymethyl)benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 96.5% |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether at 0 - 5℃; for 6h; | 96% |
Conditions | Yield |
---|---|
With sodium azide; sodium L-ascorbate In water at 60℃; for 3.5h; | 96% |
(±)-1-(4-chlorophenyl)-2-(1H-pyrrol-1-yl)ethanol
2-cyanobenzyl chloride
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% |
2-methoxy-phenol
2-cyanobenzyl chloride
2-(2-methoxyphenoxymethyl)benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 94.6% |
7-hydroxy-4-methyl-chromen-2-one
2-cyanobenzyl chloride
2-{[(4-methyl-2-coumarin-7-yl)oxy]methyl}benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 94.3% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h; | 93% |
4,6-Dimethyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile
2-cyanobenzyl chloride
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.666667h; Reflux; | 93% |
2-cyanobenzyl chloride
2-(methoxymethyl)benzonitrile
Conditions | Yield |
---|---|
With sodium methylate In methanol at 25℃; for 4h; | 93% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h; | 92% |
2-mercapto-4-methylbenzonitrile
2-cyanobenzyl chloride
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.666667h; Reflux; | 92% |
1,2,5,6,7,8-hexahydro-2-thioxoquinoline-3-carbonitrile
2-cyanobenzyl chloride
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.666667h; Reflux; | 92% |
4-(2,4-difluorophenyl)-phenol
2-cyanobenzyl chloride
2-[4-(2,4-difluorophenyl)phenoxymethyl]benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 91.5% |
2-cyanobenzyl chloride
Conditions | Yield |
---|---|
With bis(dibenzylideneacetone)-palladium(0); DavePhos In tetrahydrofuran at 25℃; for 4h; Negishi Coupling; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 90.4% |
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% |
2.6-dimethylphenol
2-cyanobenzyl chloride
2-(2,6-dimethylphenoxymethyl)benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; | 89.4% |
vanillin
2-cyanobenzyl chloride
2-((4-formyl-2-methoxyphenoxy)methyl)benzonitrile
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; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h; | 86% |
4-chloro-2-mercaptobenzonitrile
2-cyanobenzyl chloride
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.666667h; Reflux; | 86% |
3-methyl-6-chlorouracil
2-cyanobenzyl chloride
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
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℃; |
salicylonitrile
2-cyanobenzyl chloride
2-[(2-cyanobenzyl)oxy]benzonitril
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃; for 0.666667h; | 84% |
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, |
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