4-Bromo-1-chloro-2-nitrobenzene
- Product Name
- 4-Bromo-1-chloro-2-nitrobenzene
- CAS No.
- 16588-24-2
- Chemical Name
- 4-Bromo-1-chloro-2-nitrobenzene
- Synonyms
- 4-BROMO-1-CHLORO-2-NITROBENZENE;5-BROMO-2-CHLORONITROBENZENE;2-chloro-5-bromonitrobenzene;5-Bromo-1-chloro-2-nitrobenzene;1-Bromo-4-chloro-3-nitrobenzene;Benzene, 4-broMo-1-chloro-2-nitro-;4-Bromo-1-chloro-2-nitrobenzene >(dimethylamino)ethyl]-,[s-(r*,s*)]-(9ci)
- CBNumber
- CB0414522
- Molecular Formula
- C6H3BrClNO2
- Formula Weight
- 236.45
- MOL File
- 16588-24-2.mol
4-Bromo-1-chloro-2-nitrobenzene Property
- Melting point:
- 0°C
- Boiling point:
- 0°C
- Density
- 2.035 g/cm3(Temp: 16 °C)
- Flash point:
- 0°C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- soluble in Methanol
- form
- powder to crystal
- color
- White to Light yellow
- λmax
- 313nm(H2O)(lit.)
- CAS DataBase Reference
- 16588-24-2
Safety
- Hazard Codes
- Xi
- HazardClass
- IRRITANT
- HS Code
- 2904990090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B4374
- Product name
- 4-Bromo-1-chloro-2-nitrobenzene
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $40
- Updated
- 2025/07/31
- Product number
- B4374
- Product name
- 4-Bromo-1-chloro-2-nitrobenzene
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $117
- Updated
- 2025/07/31
- Product number
- B684128
- Product name
- 5-Bromo-2-chloronitrobenzene
- Packaging
- 250mg
- Price
- $55
- Updated
- 2021/12/16
- Product number
- OR6626
- Product name
- 5-Bromo-2-chloronitrobenzene
- Packaging
- 25g
- Price
- $61
- Updated
- 2021/12/16
- Product number
- FB142692
- Product name
- 4-Bromo-1-chloro-2-nitrobenzene
- Packaging
- 250g
- Price
- $300
- Updated
- 2021/12/16
4-Bromo-1-chloro-2-nitrobenzene Chemical Properties,Usage,Production
Uses
4-Bromo-1-chloro-2-nitrobenzene (5-Bromo-2-chloronitrobenzene) is a pharmaceutical intermediate compound used in the preparation of vismodegib, a molecular inhibitor of the Hedgehog signalling pathway approved for the treatment of metastatic and locally advanced basal cell carcinoma (BCC).
Synthesis
635-22-3
16588-24-2
General procedure for the synthesis of 5-bromo-2-chloronitrobenzene from 3-nitro-4-chloroaniline: 4-chloro-3-nitroaniline (17.2 g, 0.1 mol) was dissolved in 260 mL of 48% hydrobromic acid (HBr) at 0 °C. Subsequently, an aqueous solution of sodium nitrite (NaNO2, 13.8 g, 0.2 mol) was added slowly and dropwise. The reaction mixture was stirred continuously for 1 h at 0 °C. After that, cuprous bromide (CuBr, 24 g, 0.17 mol) was added in batches and stirring was continued for 1 hour at 0°C. Upon completion of the reaction, water was added and the mixture was gradually warmed to room temperature and extracted with ethyl acetate (EtOAc). The crude product was purified by silica gel column chromatography to give the final 5-bromo-2-chloronitrobenzene (13 g, 55% yield). The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 8.03-8.02 (m, 1H), 7.66-7.63 (m, 1H), 7.45-7.42 (m, 1H).
References
[1] Patent: WO2013/117522, 2013, A1. Location in patent: Page/Page column 40
[2] Patent: US2015/18367, 2015, A1. Location in patent: Paragraph 0177; 0178
[3] Journal of the American Chemical Society, 1962, vol. 84, p. 1026 - 1032
[4] Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1795 - 1799
[5] Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 10, p. 1839 - 1843
4-Bromo-1-chloro-2-nitrobenzene Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 4-Bromo-1-chloro-2-nitrobenzene manufacturers
- Product
- 5-Bromo-2-chloronitrobenzene 16588-24-2
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%+
- Supply Ability
- 400KG
- Release date
- 2022-11-04
- Product
- 5-BROMO-2-CHLORONITROBENZENE 16588-24-2
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2019-07-11