2-BROMO-4-FLUORO-6-NITROANILINE Chemical Properties

Melting point:

70-72°C

Boiling point:

313.9±37.0 °C(Predicted)

Density 

1.896±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Powder

pka

-2.32±0.25(Predicted)

color 

Orange

InChI

InChI=1S/C6H4BrFN2O2/c7-4-1-3(8)2-5(6(4)9)10(11)12/h1-2H,9H2

InChIKey

HCYDUPDSEDHSQB-UHFFFAOYSA-N

SMILES

C1(N)=C([N+]([O-])=O)C=C(F)C=C1Br

Safety Information

Hazard Codes 

T

HazardClass 

6.1

HS Code 

2921420090

2-BROMO-4-FLUORO-6-NITROANILINE Usage And Synthesis

Chemical Properties

off-white powder

Uses

2-Bromo-4-fluoro-6-nitroaniline is used as pharmaceutical intermediate.

Synthesis

The general procedure for the synthesis of 2-bromo-4-fluoro-6-nitroaniline from 4-fluoro-2-nitroaniline is as follows: 1. 4-fluoro-2-nitroaniline (10.0 g, 42.55 mmol) was dissolved in dichloromethane (DCM) to prepare a mixture. 2. a mixture of bromine (Br2, 9.9 ml, 130 mmol) in dichloromethane (110 mL, pre-cooled to 0 °C) and acetic acid (HOAc, 75 mL) was slowly added dropwise at 0 °C, with the rate of dropwise acceleration being controlled to keep the internal reaction temperature below 10 °C. 3. After titration, the reaction mixture was stirred at room temperature overnight. 4. The reaction mixture was poured into water (500 mL) to separate the organic phase. 5. The pH of the aqueous phase was adjusted to about 7 with ammonium hydroxide (NH4OH) and then the aqueous phase was extracted with dichloromethane (DCM, 100 mL x 3). 6. The organic extracts were combined, dried with magnesium sulfate (MgSO4), filtered and concentrated in vacuum to give 2-bromo-4-fluoro-6-nitroaniline as a yellow solid (14 g, 93% yield). Mass spectrum (ESI): m/z = 233 [M-1].

References

[1] Patent: US5606063, 1997, A
[2] Patent: WO2013/26914, 2013, A1. Location in patent: Page/Page column 118
[3] Patent: CN108218887, 2018, A. Location in patent: Paragraph 0094; 0097; 0098; 0099
[4] Journal of Antibiotics, 1994, vol. 47, # 12, p. 1456 - 1465
[5] Patent: US2006/229289, 2006, A1. Location in patent: Page/Page column 25

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