3-Fluoro-5-bromoaniline

3-Fluoro-5-bromoaniline Property

Boiling point:

246℃

Density 

1.694

Flash point:

102℃

storage temp. 

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

pka

2.51±0.10(Predicted)

form 

Liquid

color 

Brown

InChI

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

InChIKey

NGZAVSDIXFIWHJ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

134168-97-1

Safety

RIDADR 

UN2811

HazardClass 

6.1

HS Code 

2921420090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

3-Fluoro-5-bromoaniline Chemical Properties,Usage,Production

Synthesis

N-(3-bromo-5-fluorophenyl)acetamide (Intermediate 181, 8.7 g, 37.4 mmol) was used as a raw material, which was dissolved in ethanol (30 mL) and then concentrated hydrochloric acid (80 mL) was slowly added. The reaction mixture was heated to 100 °C and kept for 1 h for the reaction. After completion of the reaction, the mixture was cooled to room temperature and neutralized with 5 N sodium hydroxide solution. The crude product was extracted with ethyl acetate (2 x 100 mL) and the combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by concentration under reduced pressure. Purification by silica gel column chromatography using a gradient elution with 5-10% ethyl acetate in hexane solution gave 5.3 g (75% yield) of the yellow oily target product 3-bromo-5-fluoroaniline (Intermediate 180). Mass spectrum (ES+): m/z 190, 192 ([M+H]+), molecular formula C6H5BrFN. 1H NMR (DMSO-d6) δ: 5.46-6.00 (m, 2H), 6.24-6.37 (m, 1H), 6.44-6.53 (m, 1H), 6.54-6.61 (m, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5477 - 5480
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 22, p. 5061 - 5064
[3] Patent: WO2006/134378, 2006, A1. Location in patent: Page/Page column 149