2-Bromo-4-trifluoromethoxyaniline Chemical Properties

Boiling point:

209 °C(lit.)

Density 

1.693 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.504(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Liquid

pka

1.68±0.10(Predicted)

color 

Clear light yellow to orange-yellow

Specific Gravity

1.693

InChI

InChI=1S/C7H5BrF3NO/c8-5-3-4(1-2-6(5)12)13-7(9,10)11/h1-3H,12H2

InChIKey

ROSTYHNIIDIBEG-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(OC(F)(F)F)C=C1Br

CAS DataBase Reference

175278-17-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

IRRITANT

HS Code 

29222990

MSDS

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

2-Bromo-4-trifluoromethoxyaniline Usage And Synthesis

Chemical Properties

clear light yellow to orange-yellow liquid

Synthesis

General procedure for the synthesis of 2-bromo-4-trifluoromethoxyaniline from 4-(trifluoromethoxy)aniline: N-bromosuccinimide (3.62 g, 20.34 mmol) was slowly added to a solution of 4-(trifluoromethoxy)aniline (3.00 g, 16.9 mmol) in acetonitrile (30 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by column chromatography using 10% ethyl acetate/hexane as eluent to give 2-bromo-4-trifluoromethoxyaniline as a brown oil (3.6 g, 83% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 4.11 (broad single peak, 2H), 6.73 (double peak, 1H), 6.99 (double-double-heavy peak, 1H), and 7.31 (double-heavy peak, 1H).The LC-MS analysis showed that the [M-H]- peak was located at m/z 253.1.

References

[1] Patent: WO2015/100232, 2015, A2. Location in patent: Page/Page column 102
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 1, p. 113 - 128
[3] Patent: EP1183229, 2005, B1. Location in patent: Page/Page column 143-144
[4] Organic Letters, 2011, vol. 13, # 20, p. 5636 - 5639
[5] Journal of the American Chemical Society, 2016, vol. 138, # 40, p. 13147 - 13150

2-Bromo-4-trifluoromethoxyaniline(175278-17-8)Related Product Information

• (Trifluoromethoxy)benzene
• 4'-(Trifluoromethoxy)acetophenone
• 2-Bromoaniline
• 2-Aminobenzotrifluoride
• 4-(Trifluoromethoxy)chlorobenzene
• 4-Aminobenzotrifluoride
• Aniline
• p-Anisaldehyde
• Anisole
• 3-Methoxyacetophenone
• 4-Bromoaniline
• p-Anisidine
• 4-Methoxybenzyl alcohol
• 4-Methoxybenzyl cyanide
• 4-Methoxybenzoyl chloride
• p-Trifluoromethoxy phenol
• o-Anisidine
• ANILINE BLACK