ChemicalBook Product Catalog Organic Chemistry Nitrile compound 4-Chlorobenzyl cyanide

4-Chlorobenzyl cyanide

Product Name4-Chlorobenzyl cyanide
CAS140-53-4
MFC8H6ClN
MW151.59
EINECS205-418-9
MOL File140-53-4.mol

Chemical Properties

Melting point	25-28 °C(lit.)
Boiling point	265-267 °C(lit.)
Density	1.19 g/mL at 20 °C(lit.)
refractive index	n20/D 1.543
Flash point	>230 °F
storage temp.	Sealed in dry,Room Temperature
solubility	0.3g/l
form	Liquid After Melting
color	Clear colorless to yellow
BRN	971171
Exposure limits	NIOSH: IDLH 25 mg/m3
InChI	1S/C8H6ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2
InChIKey	IVYMIRMKXZAHRV-UHFFFAOYSA-N
SMILES	Clc1ccc(CC#N)cc1
CAS DataBase Reference	140-53-4(CAS DataBase Reference)
NIST Chemistry Reference	Benzeneacetonitrile, 4-chloro-(140-53-4)
EPA Substance Registry System	Benzeneacetonitrile, 4-chloro- (140-53-4)

Safety Information

Hazard Codes	T,Xi
Risk Statements	23/24/25-36/37/38
Safety Statements	26-36/37/39-45-28B
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	AL8250000
Hazard Note	Irritant/Toxic
TSCA	TSCA listed
HazardClass	6.1
PackingGroup	II
HS Code	29269095
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 2 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
4-Chlorobenzyl cyanide	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

clear colorless to yellowish liquid after melting. Soluble in acetone and ethanol.

Uses

4-Chlorobenzyl cyanide is an intermediate for the preparation of 3-methyl-2-(4-chlorophenyl)butyric acid, which can be used to prepare pyrethroid insecticides such as fenvalerate and deltamethrin, and can be used in medicine Industrial preparation of pyrimethamine.

Preparation

4-Chlorobenzyl cyanide is obtained by the reaction of 4-Chlorobenzyl chloride with sodium cyanide. Add 4-Chlorobenzyl chloride and Benzyldodecyldimethylammonium bromide into the reaction pot, heat to 100°C, slowly add sodium cyanide aqueous solution, and react at 100-104°C for 5h (add sodium cyanide for 3h, keep warm for 2h). Then add water to dissolve sodium chloride, and separate the water layer to obtain the crude benzyl chloride cyanide, which is distilled under reduced pressure to collect 160 (2.66kPa) fractions to obtain the finished product of 4-Chlorobenzyl cyanide. The yield is above 81%.

Definition

ChEBI: 4-Chlorobenzyl cyanide is a nitrile that is acetonitrile in which one of the hydrogens has been replaced by a p-chlorophenyl group. It is a member of monochlorobenzenes and a nitrile. It derives from an acetonitrile.

Synthesis

4251-65-4

140-53-4

Microwave radiation synthesis procedure: p-chlorophenylacetaldehyde (0.106 g, 1 mmol), hydroxylamine hydrochloride (0.083 g, 1.2 mmol) and catalyst (15 mol%) were mixed in a microwave reactor and the reaction was carried out by radiation at 140°C for 10 min. The reaction process was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature. The products were extracted using ethyl acetate (EtOAc). Subsequently, EtOAc was removed by rotary evaporator to obtain a solid product. The solid product was further purified by silica gel column chromatography. Finally, the purified p-chlorobenzeneacetonitrile was confirmed by gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance hydrogen spectroscopy (1H NMR) for characterization.

References

[1] Synthesis (Germany), 2013, vol. 45, # 23, p. 3295 - 3299
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 16, p. 2379 - 2384

4-Chlorobenzyl cyanide

Chemical Properties

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MSDS

Usage And Synthesis

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