2-Chloro-4-fluorobenzyl bromide Chemical Properties

Melting point:

33-35°C

Boiling point:

226.8±25.0 °C(Predicted)

Density 

1.3879 (rough estimate)

refractive index 

1.5550 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

soluble in Methanol

form 

Crystalline Low Melting Mass

color 

White to yellow

Sensitive 

Lachrymatory

BRN 

3539265

InChI

InChI=1S/C7H5BrClF/c8-4-5-1-2-6(10)3-7(5)9/h1-3H,4H2

InChIKey

GAUUDQVOPUKGJD-UHFFFAOYSA-N

SMILES

C1(CBr)=CC=C(F)C=C1Cl

CAS DataBase Reference

45767-66-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

34-22

Safety Statements 

45-36/37/39-26

RIDADR 

3265

Hazard Note 

Corrosive/Lachrymatory

HazardClass 

8

PackingGroup 

III

HS Code 

29039990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloro-4-fluorobenzyl bromide Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-Chloro-4-fluorobenzyl bromide is used as a reagent in the synthesis of a variety of compounds, such as pharmaceuticals, agrochemicals, and industrial chemicals.

Synthesis

General procedure for the synthesis of 2-chloro-4-fluorobenzyl bromide from 2-chloro-4-fluorotoluene: A mixture of 77.6 g (0.54 mol) of 2-chloro-4-fluorotoluene, 95.6 g (0.54 mol) of N-bromosuccinimide, 1 g of benzoyl peroxide, and 1,000 mL of carbon tetrachloride was heated and refluxed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a G3 glass sand core funnel. The precipitate was washed with 3 x 100 mL of carbon tetrachloride. The filtrates were combined and concentrated to dryness under reduced pressure. The residue was purified by fractional distillation and the fractions with boiling points of 97-99 °C/10 mmHg were collected to give pure 2-chloro-4-fluorobenzyl bromide in a yield of 106 g (88% yield). Elemental analysis (C7H5BrClF) Calculated values: C, 37.62; H, 2.26; measured values: C, 37.79; H, 2.34. 1H NMR (CDCl3) δ: 7.41 (dt, J = 8.4 Hz, 6.0 Hz, 1H, 6-H), 7.13 (dt, J = 8.4 Hz, 2.6 Hz, 1H, 3-H), and 6.97 (dt, J = 8.4 Hz, 2.6 Hz, 1H, 5-H), 4.55 (s, 2H, CH2).

References

[1] Patent: WO2007/70041, 2007, A1. Location in patent: Page/Page column 115
[2] Journal of Organic Chemistry, 1983, vol. 48, # 4, p. 526 - 532
[3] Patent: US2007/135595, 2007, A1

2-Chloro-4-fluorobenzyl bromide(45767-66-6)Related Product Information

• 2-(Trifluoromethyl)benzyl chloride
• 2-Chlorobenzyl chloride
• Chlorobromoisocyanurate
• Allyl bromide
• BCDMH
• Benzyl bromide
• Sodium bromate
• alpha-Chloro-o-fluorotoluene
• Rocuronium bromide
• Benzyl chloroformate
• Ethidium bromide
• 4-Nitrobenzyl bromide
• Methyl bromide
• Difluorochloromethane
• 2-Chlorobenzyl bromide
• 2-Chloro-4-fluorotoluene
• 2-CHLORO-4,5-DIFLUOROBENZYL BROMIDE
• 3-Fluorobenzyl bromide