2-Bromo-3-fluoroaniline

2-Bromo-3-fluoroaniline Property

Melting point:

32-34 °C

Boiling point:

229.8±20.0 °C(Predicted)

Density 

1.670

Flash point:

94°(201°F)

refractive index 

1.5830

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Crystalline

pka

1.52±0.10(Predicted)

color 

Off-white

Water Solubility 

Slightly soluble in water.

InChI

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

InChIKey

XZRSXRUYZXBTGD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

111721-75-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

22-36-36/37/38-20/21/22

Safety Statements 

9-26-36/37-60

RIDADR 

2811

Hazard Note 

Harmful/Irritant

HazardClass 

6.1

HS Code 

29214200

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.

2-Bromo-3-fluoroaniline Chemical Properties,Usage,Production

Chemical Properties

Light yellow liquid

Uses

2-Bromo-3-fluoroaniline is used as pharmaceutical intermediate.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 2151, 1990 DOI: 10.1002/jhet.5570270755

Synthesis

General procedure for the synthesis of 2-bromo-3-fluoroaniline from 2-bromo-3-fluoro nitrobenzene: 2-bromo-1-fluoro-3-nitrobenzene (1.0 g, 5.0 mmol) was dissolved in methanol (50 mL) at 0 °C, and NiCl? (2.2 g, 10 mmol) and NaBH? (0.50 g, 14 mmol) were added sequentially. After the addition was completed, the reaction mixture was stirred at 0 °C for 5 min. Subsequently, the reaction was quenched by the addition of water (20 mL) and extracted with ethyl acetate (20 mL x 3). The organic layers were combined, dried over anhydrous Na?SO? and concentrated under reduced pressure to afford 2-bromo-3-fluoroaniline (600 mg, 70% yield). The product was characterized by 1H NMR (400 MHz, CDCl?): δ 7.07-7.02 (m, 1H), 6.55-6.49 (m, 1H), 4.22 (br s, 2H).

References

[1] Patent: CN108002976, 2018, A. Location in patent: Paragraph 0045; 0047; 0050; 0051; 0060; 0069
[2] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437
[3] Patent: US2007/244159, 2007, A1. Location in patent: Page/Page column 121
[4] Patent: US2011/98311, 2011, A1
[5] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 1674