2-Bromo-3-fluoroaniline Chemical Properties

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 Information

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

2-Bromo-3-fluoroaniline Usage And Synthesis

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

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