4-Bromo-2-fluorobenzyl bromide Chemical Properties

Melting point:

33-36 °C (lit.)

Boiling point:

126 °C (19 mmHg)

Density 

1.9094 (rough estimate)

refractive index 

1.5770 (estimate)

Flash point:

126°C/9mm

storage temp. 

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

solubility 

soluble in Methanol

form 

Low Melting Solid

color 

White to off-white

Sensitive 

Lachrymatory

BRN 

4307676

InChI

InChI=1S/C7H5Br2F/c8-4-5-1-2-6(9)3-7(5)10/h1-3H,4H2

InChIKey

XMHNLZXYPAULDF-UHFFFAOYSA-N

SMILES

C1(CBr)=CC=C(Br)C=C1F

CAS DataBase Reference

76283-09-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

22-34-52/53-20/21/22

Safety Statements 

26-36/37/39-45-61

RIDADR 

UN 2923 8/PG 3

WGK Germany 

2

Hazard Note 

Corrosive/Lachrymatory

HazardClass 

8

PackingGroup 

III

HS Code 

29039990

MSDS

• Language:English Provider:4-Bromo-1-(bromomethyl)-2-fluoro-benzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromo-2-fluorobenzyl bromide Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

4-Bromo-2-fluorobenzyl bromide may be used in the synthesis of 1-(2-fluoro-4-(1-methyl-1H-pyrazol-4-yl)benzyl)indoline-2,3-dione.

General Description

4-Bromo-2-fluorobenzyl bromide is a substituted benzyl bromide. Its density is 1.9094g/ml at 25°C.

Synthesis

General procedure for the synthesis of 2-fluoro-4-bromobenzyl bromide from 2-fluoro-4-bromotoluene: N-bromosuccinimide (NBS, 1.07 g, 6.05 mmol) and azobisisobutyronitrile (AIBN, 83 mg, 0.50 mmol) were dissolved in carbon tetrachloride (CCl4, 10 mL), followed by addition of 2-fluoro-4-bromotoluene (1 g, 5.04 mmol). The reaction mixture was heated to reflux at 100 °C for 13 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the resulting solid was collected by filtration. The filtrate was extracted several times with carbon tetrachloride and water. The organic layers were combined and dried with anhydrous sodium sulfate to remove residual water. Subsequently, the organic layer was concentrated under reduced pressure to afford 4-bromo-1-(bromomethyl)-2-fluorobenzene (1.2 g, 4.47 mmol) in 89% yield. The product was characterized by 1H-NMR (300 MHz, CDCl3): δ 7.51-7.41 (m, 1H), 7.09 (d, J=9.0 Hz, 1H), 6.99 (d, J=8.2 Hz, 1H), 4.34 (s, 2H).

References

[1] Patent: US2015/259350, 2015, A1. Location in patent: Paragraph 0169; 1070
[2] Patent: KR101745741, 2017, B1. Location in patent: Paragraph 0268
[3] Patent: WO2014/76104, 2014, A1. Location in patent: Page/Page column 66
[4] Journal of Medicinal Chemistry, 1995, vol. 38, # 15, p. 2938 - 2945
[5] European Journal of Pharmaceutical Sciences, 2006, vol. 27, # 2-3, p. 188 - 193

4-Bromo-2-fluorobenzyl bromide(76283-09-5)Related Product Information

• Allylbenzene
• Bromotrimethylsilane
• Benzyl bromide
• Sodium bromate
• 4-Bromo-2-fluorobenzoic acid
• 3-Bromoanisole
• Florfenicol
• Clidinium bromide
• Ethyl bromodifluoroacetate
• Ethidium bromide
• Benzyl benzoate
• 4-Bromobenzotrifluoride
• BRETYLIUM TOSYLATE
• Benzyl butyrate
• Benzyl chloride
• Transfluthrin
• Benzyl alcohol
• Benzene