3-Fluoro-4-broMoaniline Chemical Properties

Melting point:

72-73°C

Boiling point:

65-68 °C (lit.)

Density 

0.982 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.471(lit.)

Flash point:

105 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetonitrile, Methanol

form 

Crystalline Powder

pka

2.88±0.10(Predicted)

color 

Yellow to tan

Water Solubility 

Soluble in acetonitrile, methanol. Insoluble in water.

BRN 

3236457

InChI

InChI=1S/C6H5BrFN/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2

InChIKey

YTMVYYAKOPIJCZ-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(Br)C(F)=C1

CAS DataBase Reference

656-65-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

MSDS

• Language:English Provider:4-Bromo-3-fluoroaniline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Fluoro-4-broMoaniline Usage And Synthesis

Chemical Properties

Beige to brown needles and crystalline powder

Uses

4-Bromo-3-fluoroaniline is an intermediate used for the synthetic preparation of Tradizolid and various pharmaceuticals such as the synthesis of several lateral difluoro-substituted 4,4"-dialkyl- and 4,4"-alkoxyalkylterphenyls.

Uses

4-Bromo-3-fluoroaniline is a intermediate used for the synthetic preparation of Tradizolid and various pharmaceuticals such as the synthesis of several lateral difluoro-substituted 4,4"-dialkyl- and 4 ,4"-alkoxyalkylterphenyls.

Synthesis

General procedure for the synthesis of 4-bromo-3-fluoroaniline from 3-fluoro-4-bromoacetanilide: N-(4-bromo-3-fluorophenyl)acetamide (12.9 g, 12.9 mmol) was dissolved in ethanol (30 mL), and stirred until completely dissolved. Subsequently, concentrated hydrochloric acid (15 mL) was added to the solution and the reaction was refluxed at 80 °C for 4 hours. Upon completion of the reaction, the reaction mixture was diluted with ice water and extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and brine solution. Finally, the solvent was removed by vacuum distillation to afford 4-bromo-3-fluoroaniline (2.45 g, 100.0% yield) as an off-white solid.

References

[1] Patent: WO2014/202580, 2014, A1. Location in patent: Page/Page column 97; 98
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64
[3] Journal of the Chemical Society, 1958, p. 2815,2818

3-Fluoro-4-broMoaniline(656-65-5)Related Product Information

• 4-(Trifluoromethoxy)aniline
• 4-Fluoroaniline
• 2-Bromoaniline
• 2,4,5-Trifluoroaniline
• Ethyl bromodifluoroacetate
• 3-Fluoroaniline
• 2-Fluoroaniline
• 4-Bromoaniline
• Torezolid
• bis(((R)-3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl) hydrogen phosphate
• Tedizolid Impurity 36
• (S)-(+)-Glycidyl butyrate
• Tedizolid Impurity 39
• (R)-(3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl) phenyl)-2-oxooxazolidin-5-yl)methyl butyrate
• (R)-Glycidyl butyrate
• (R)-3-(4-(6-(1H-tetrazol-5-yl)pyridin-3-yl)-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one
• Tedizolid phosphate impurity
• 5-Bromo-2-pyridinecarbonitrile