1-BROMO-2-CHLORO-3-NITROBENZENE Chemical Properties

Melting point:

57-60°C

Boiling point:

290.4±20.0 °C(Predicted)

Density 

1.827±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

Pale Yellow

InChI

InChI=1S/C6H3BrClNO2/c7-4-2-1-3-5(6(4)8)9(10)11/h1-3H

InChIKey

JNIDAGAFFKAPRV-UHFFFAOYSA-N

SMILES

C1(Br)=CC=CC([N+]([O-])=O)=C1Cl

Safety Information

HS Code 

2902900000

1-BROMO-2-CHLORO-3-NITROBENZENE Usage And Synthesis

Uses

1-Bromo-2-chloro-3-nitrobenzene is a reagent used in pharmaceutical synthesis. Used in the synthesis of benzodiazepinone bromodomain inhibitor CPI-?637 which may be applicable to cancer therapies.

Synthesis

General procedure for the synthesis of 1-bromo-2-chloro-3-nitrobenzene from 2-chloro-3-nitrobenzoic acid: 2-chloro-3-nitrobenzoic acid (15 g, 74.4 mmol) was dissolved in 350 mL of carbon tetrachloride under nitrogen protection and red mercuric oxide (24.3 g, 111.62 mmol) was added. The mixture was heated to 87°C under light conditions to reflux and bromine (5.75 mL, 111.6 mmol) was added slowly and dropwise. After the dropwise addition was completed, the reaction was continued at reflux for 3 h, followed by cooling to room temperature. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution, stirred for 10 min and filtered through a diatomaceous earth pad. The filter cake was further washed with dichloromethane. The organic layer was separated, washed sequentially with water and brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 11.55 g of 1-bromo-2-chloro-3-nitrobenzene in 67% yield. The product was detected by 400 MHz 1H NMR (CDCl3) with chemical shifts of δ 7.84 (d, 1H), 7.71 (d, 1H), 7.27 (dd, 1H); and mass spectra (M + 1) of 235, 237, 239.

References

[1] Journal of Medicinal Chemistry, 1996, vol. 39, # 23, p. 4654 - 4666
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 20, p. 5392 - 5397
[3] Patent: WO2004/69832, 2004, A2. Location in patent: Page 126-127
[4] Patent: US2009/197932, 2009, A1. Location in patent: Page/Page column 5
[5] Patent: WO2008/12623, 2008, A1. Location in patent: Page/Page column 61

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