3-(Trifluoromethoxy)bromobenzene Chemical Properties

Boiling point:

156-158 °C

Density 

1.62 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.462(lit.)

Flash point:

145 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

1.64

BRN 

1945938

InChI

InChI=1S/C7H4BrF3O/c8-5-2-1-3-6(4-5)12-7(9,10)11/h1-4H

InChIKey

WVUDHWBCPSXAFN-UHFFFAOYSA-N

SMILES

C1(Br)=CC=CC(OC(F)(F)F)=C1

CAS DataBase Reference

2252-44-0(CAS DataBase Reference)

NIST Chemistry Reference

3-(Trifluoromethoxy)bromobenzene(2252-44-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29049090

MSDS

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

3-(Trifluoromethoxy)bromobenzene Usage And Synthesis

Chemical Properties

Clear very faintly yellow liquid

Uses

1-Bromo-3-(trifluoromethoxy)benzene may be used in the preparation of 1,2-dehydro-3-(trifluoromethoxy)benzene. It may be used in the synthesis of new electronically deficient atropisomeric diphosphine ligand (S)-CF₃O-BiPhep [2,2′-bis(diphenylphosphino)-6,6′-ditrifluoromethoxy-1,1′-biphenyl].

General Description

1-Bromo-3-(trifluoromethoxy)benzene undergoes Diels-Alder reaction with lithium diisopropylamide (LDA) in THF and furan, to yield the corresponding 1,4-dihydro-1,4-epoxy-5- or 6-(trifluoromethoxy)naphthalenes.

Synthesis

The general procedure for the synthesis of 3-trifluoromethoxybromobenzene from p-trifluoromethoxyaniline is described below: Example 5 (comparative experiment) Preparation of 1-bromo-3-trifluoromethoxybenzene using bromine (Br2) in acetic acid medium. This was done as follows: 60 g of acetic acid was added to a 100 mL round bottom flask, followed by the slow addition of 30 g of 4-trifluoromethoxyaniline. After cooling the reaction mixture to 0-5 °C, 27 g of bromine was slowly added dropwise. Upon completion of the reaction, the reaction mixture was analyzed by gas chromatography, which showed 20% unreacted 4-trifluoromethoxyaniline, 37% monobrominated derivatives and more than 41% dibrominated derivatives.

References

[1] Patent: WO2007/107820, 2007, A2. Location in patent: Page/Page column 9
[2] Patent: WO2007/107820, 2007, A2. Location in patent: Page/Page column 9

3-(Trifluoromethoxy)bromobenzene(2252-44-0)Related Product Information

• 4-Bromofluorobenzene
• 4-Bromobenzotrifluoride
• Xylene
• 4-(Trifluoromethoxy)aniline
• 4-Bromoanisole
• Bromobenzene
• 3-Bromoanisole
• 2-Bromofluorobenzene
• 3-Bromobenzotrifluoride
• 3-Bromofluorobenzene
• (Trifluoromethoxy)benzene
• 2-Bromobenzonitrile
• 3-Bromobenzonitrile
• 1-BROMO-3-TRIMETHYLSILYLBENZENE
• 1,3-Dibromobenzene
• Benzene
• 2-Bromo-4-trifluoromethoxyaniline
• 4-BROMO-2-(TRIFLUOROMETHOXY)BENZENE-1-SULFONYL CHLORIDE