3,4,5-TRIFLUOROBENZYL BROMIDE Chemical Properties

Boiling point:

44-46°C 1mm

Density 

1.689 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5050(lit.)

Flash point:

150 °F

storage temp. 

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

form 

clear liquid

color 

Light yellow to Brown

Sensitive 

Lachrymatory

BRN 

8680985

InChI

InChI=1S/C7H4BrF3/c8-3-4-1-5(9)7(11)6(10)2-4/h1-2H,3H2

InChIKey

MPEKZIYOLQCWLL-UHFFFAOYSA-N

SMILES

C1(F)=CC(CBr)=CC(F)=C1F

CAS DataBase Reference

220141-72-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 1760 8/PG 3

WGK Germany 

3

Hazard Note 

Corrosive/Lachrymatory

TSCA 

T

HazardClass 

8

PackingGroup 

II

HS Code 

29039990

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Eye Dam. 1
Skin Corr. 1B

MSDS

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

3,4,5-TRIFLUOROBENZYL BROMIDE Usage And Synthesis

Uses

3,4,5-Trifluorobenzyl bromide is an organic intermediate.

Chemical Properties

Colorless liquid

Synthesis

The 3,4,5-trifluorobenzyl bromide can be obtained from 3,4,5-trifluorobenzaldehyde by first preparing (3,4,5-trifluorophenyl)methanol as raw material and then brominating to obtain 3,4,5-trifluorobenzyl bromide.

Step A: (3,4,5-Trifluorophenyl)methanol:

To a cooled (-5??C) solution of 3,4,5-trifluorobenzaldehyde (7.0 g, 43.75 mmol) in a mixture of THF and water (50 ml, 9:1) was added slowly in batches over a period of 30 min, NaBH4 (1.662 g, 43.75 mmol). This reaction mixture was brought to room temperature over a period of 2h and carefully poured into ice-cold dilute HCl (200 ml, 1N). The oil layer was extracted into CH2Cl2 (250 ml) and the organic layer was washed with water (200 ml), dried (MgSO4) and evaporated. The resulting crude product (7.08 g, quantitatively) was continued without further purification.

Step B: 3,4,5-Trifluorobenzyl bromide:

To a solution of (3,4,5-trifluorophenyl)methanol (40 mmol) in CH2Cl2 (150 ml) was slowly added a solution of thionyl bromide (6.16 ml, 80 mmol) in CH2Cl2 (50 ml). This reaction mixture was stirred for 16h at room temperature and poured into ice water (200ml). The organic layer was separated, washed with saturated NaHCO3 (2 x 200 ml), water (200 ml), dried (MgSO4) and evaporated to give the corresponding light yellow oily bromo compound in quantitative yield.

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