4-(Chloromethyl)tolunitrile Chemical Properties

Melting point:

77 °C

Boiling point:

263 °C

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Methanol

form 

Crystalline Powder

color 

Off-white to pale yellow

BRN 

742357

InChI

InChI=1S/C8H6ClN/c9-5-7-1-3-8(6-10)4-2-7/h1-4H,5H2

InChIKey

LOQLDQJTSMKBJU-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(CCl)C=C1

CAS DataBase Reference

874-86-2(CAS DataBase Reference)

NIST Chemistry Reference

4-(CH2Cl)-C6H4-CN(874-86-2)

Safety Information

Hazard Codes 

T,C

Risk Statements 

20/21-65-36/37/38-32-23/25-34-22

Safety Statements 

23-36-45-36/37/39-26-24/25

RIDADR 

3276

WGK Germany 

2

HazardClass 

8

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:ALFA

4-(Chloromethyl)tolunitrile Usage And Synthesis

Application

p-Cyanobenzyl chloride is a white, needle-like solid at room temperature and pressure. It belongs to the benzonitrile derivative class and can be used as an intermediate in organic and biochemical synthesis, particularly for the derivatization of drug molecules and bioactive molecules. Furthermore, p-cyanobenzyl chloride also has some applications in the preparation of fluorescent whitening agents.

Chemical Properties

White to light yellow crystal powde

Synthesis

General procedure for the synthesis of p-cyanobenzyl chloride from 4-chloromethylstyrene: 0.4 mmol of 4-chloromethylstyrene, 2 mmol of sodium nitrite, 5 mg of metal iron(III) porphyrin catalyst, and 4.5 mL of acetonitrile solvent were added to the reaction tube. The mixture was heated to 70 °C under air atmosphere and stirred. 0.5 mL of formic acid was added slowly and dropwise over the first 0.5 hr of the start of the reaction. After the reaction lasted for 4 hours, the heating and stirring was stopped and the reaction mixture was cooled to room temperature. The solvent was removed using a rotary evaporator to obtain the crude product. The crude product was purified by column chromatography and the eluent was a solvent mixture of petroleum ether and ethyl acetate. The final target product, p-chloromethylbenzonitrile, was obtained as a white solid in 96.2% yield. The NMR data are shown below.

References

[1] Patent: CN107573259, 2018, A. Location in patent: Paragraph 0133-0137
[2] Tetrahedron Letters, 2016, vol. 57, # 24, p. 2620 - 2623

4-(Chloromethyl)tolunitrile(874-86-2)Related Product Information

• 4-Cyanobenzylamine
• 2-Methylbenzyl chloride
• 4-Cyanophenol
• 4-Nitrobenzyl chloroformate
• Benzyl chloroformate
• 4-tert-Butylbenzyl chloride
• 4-Methoxybenzylchloride
• 4-Chlorobenzyl cyanide
• 3-Methoxybenzyl chloride
• 4-Methylbenzyl chloride
• 2-Chlorobenzyl chloride
• Benzonitrile
• 4-Chlorobenzyl chloride
• 4-Fluorobenzyl chloride
• 2-(Chloromethyl)tolunitrile
• 4,4'-(Chloromethylene)-bis-benzonitrile
• 4-Cyanobenzoyl chloride
• Benzeneacetonitrile