4-(Trifluoromethoxy)benzyl bromide Chemical Properties

Melting point:

22-24°C

Boiling point:

82-84 °C10 mm Hg(lit.)

Density 

1.594 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.48(lit.)

Flash point:

202 °F

storage temp. 

Refrigerated.

solubility 

soluble in Chloroform, Methanol

form 

Liquid or Low Melting Solid

Specific Gravity

1.594

color 

Clear faintly yellow

Sensitive 

Lachrymatory

BRN 

2521451

InChI

InChI=1S/C8H6BrF3O/c9-5-6-1-3-7(4-2-6)13-8(10,11)12/h1-4H,5H2

InChIKey

JDNPUJCKXLOHOW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

50824-05-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-28-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

Hazard Note 

Corrosive/Lachrymatory

HazardClass 

8

PackingGroup 

III

HS Code 

29093090

MSDS

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

4-(Trifluoromethoxy)benzyl bromide Usage And Synthesis

Uses

4-Trifluoromethoxybenzyl Bromide is a useful synthetic intermediate. It is used to prepare (nitro)[(trifluoromethoxy)benzyloxy]dihydroimidazo[2,1-b][1,3]oxazines with antitubercular activities. It is also used to synthesize tetrahydronaphthalenols with anti-allergic activities.

Chemical Properties

Colorless to light yellow liqui

Uses

4-(Trifluoromethoxy)benzyl bromide may be used in the synthesis of bioreductive drug, (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).

General Description

Polymerizations of 4-(trifluoromethoxy)benzyl bromide, via Friedel-Crafts polymerization using aluminum chloride as a catalyst has been reported.

Synthesis

Synthesis of 1-(bromomethyl)-4-(trifluoromethoxy)benzene: Phosphorus tribromide (6 g, 22.2 mmol) was slowly added dropwise to a solution of (4-(trifluoromethoxy)phenyl)methanol (3.6 g, 18.8 mmol) in dichloromethane (60 mL) at 0-10 °C and stirred for 30 min. The reaction mixture was then continued to stir at room temperature for 3 hours. Upon completion of the reaction, the reaction was terminated by the addition of water (30 mL) and the mixture was washed sequentially with aqueous sodium bicarbonate (2 x 30 mL) and brine (30 mL). The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 4-trifluoromethoxybenzyl bromide (3.5 g, 66% yield) as a yellow oil.

References

[1] Patent: US2007/270434, 2007, A1. Location in patent: Page/Page column 17
[2] J. Gen. Chem. USSR (Engl. Transl.), 1965, vol. 35, p. 1631 - 1637
[3] Zhurnal Obshchei Khimii, 1965, vol. 35, p. 1628 - 1636
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 2, p. 556 - 568
[5] Organometallics, 2014, vol. 33, # 21, p. 5940 - 5943

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