5-Chloro-2-fluorobenzyl bromide

5-Chloro-2-fluorobenzyl bromide Property

Melting point:

45°/0.5mm

Boiling point:

44-45°C 0,5mm

Density 

1.65

refractive index 

1.565

Flash point:

44-45°C/0.5mm

storage temp. 

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

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Sensitive 

Lachrymatory

BRN 

637765

CAS DataBase Reference

71916-91-1(CAS DataBase Reference)

Safety

Hazard Codes 

C,Xn

Risk Statements 

34-36/37/38-22

Safety Statements 

26-36/37/39-45

RIDADR 

3265

Hazard Note 

Corrosive/Lachrymatory

HazardClass 

8

PackingGroup 

III

HS Code 

29039990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H227Combustible liquid

H290May be corrosive to metals

H314Causes severe skin burns and eye damage

H318Causes serious eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P234Keep only in original container.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P309IF exposed or if you feel unwell:

P310Immediately call a POISON CENTER or doctor/physician.

P390Absorb spillage to prevent material damage.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P406Store in corrosive resistant/… container with a resistant inner liner.

P501Dispose of contents/container to..…

5-Chloro-2-fluorobenzyl bromide Chemical Properties,Usage,Production

Uses

2-(bromomethyl)-4-chloro-1-fluoro-Benzene is a useful reactant which has been used in the synthesis of potential cell cycle inhibitors in HepG2 cells.

Synthesis

General procedure for the synthesis of 5-chloro-2-fluorobenzyl bromide from 5-chloro-2-fluorotoluene: A: 5-Chloro-2-fluorotoluene (100 g, 692 mmol) was dissolved in ethyl acetate (300 ml) at 20 °C. To this solution N-bromosuccinimide (147.7 g, 830 mmol) and dibenzoyl peroxide (2 g, 8.25 mmol) were added sequentially. The reaction mixture was heated to 80 °C and stirred for 3 hours. Upon completion of the reaction, heptane (300 ml) was added and the mixture was cooled to 0 °C, at which time the succinimide precipitated. After filtration and washing with heptane, the residue was washed with water (1500 ml). The filtrate was concentrated to dryness under vacuum to give 162 g of the crude product 5-chloro-2-fluorobenzyl bromide. The crude product (141 g) was purified by vacuum distillation at 99 °C and 33 mbar to give the final 5-chloro-2-fluorobenzyl bromide (99 g, 75% yield). The purity of the product was analyzed by GC to be 87.1% (% area).1H-NMR (CDCl3) data: δ 4.44 (2H, d, CH2), 7.01 (1H, t, H3), 7.26 (1H, m, H4), 7.38 (1H, m, H6).

References

[1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 1, p. 27 - 32
[2] Patent: WO2008/3460, 2008, A1. Location in patent: Page/Page column 23-24
[3] Patent: US2008/9619, 2008, A1. Location in patent: Page/Page column 11-12
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 10, p. 3098 - 3105
[5] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 19, p. 2903 - 2909