2,5-dibromo-4-nitro-1H-imidazole
- Product Name
- 2,5-dibromo-4-nitro-1H-imidazole
- CAS No.
- 6154-30-9
- Chemical Name
- 2,5-dibromo-4-nitro-1H-imidazole
- Synonyms
- Nsc 222400;2,5-dibromo-4-nitro;2,4-Dibromo-5-nitroimidazole;2,5-Dibromo-4-nitroimidazole;Imidazole, 2,4-dibromo-5-nitro-;2,4-Dibromo-5-nitro-1H-imidazole;2,5-dibromo-4-nitro-1H-imidazole;2,4(5)-dibromo-5(4)-nitroimidazole;1H-IMidazole, 2,4-dibroMo-5-nitro-;1H-Imidazole, 2,5-dibromo-4-nitro-
- CBNumber
- CB01527904
- Molecular Formula
- C3HBr2N3O2
- Formula Weight
- 270.87
- MOL File
- 6154-30-9.mol
2,5-dibromo-4-nitro-1H-imidazole Property
- Melting point:
- >270 °C
- Boiling point:
- 396℃
- Density
- 2.575
- Flash point:
- 193℃
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- pka
- 2.93±0.10(Predicted)
- Appearance
- White to off-white Solid
- CAS DataBase Reference
- 6154-30-9
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
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
- CS-0060033
- Product name
- 2,5-Dibromo-4-nitro-1H-imidazole
- Purity
- 99.03%
- Packaging
- 1g
- Price
- $52
- Updated
- 2021/12/16
- Product number
- CS-0060033
- Product name
- 2,5-Dibromo-4-nitro-1H-imidazole
- Purity
- 99.03%
- Packaging
- 250mg
- Price
- $53
- Updated
- 2021/12/16
- Product number
- CS-0060033
- Product name
- 2,5-Dibromo-4-nitro-1H-imidazole
- Purity
- 99.03%
- Packaging
- 5g
- Price
- $146
- Updated
- 2021/12/16
- Product number
- CS-0060033
- Product name
- 2,5-Dibromo-4-nitro-1H-imidazole
- Purity
- 99.03%
- Packaging
- 10g
- Price
- $248
- Updated
- 2021/12/16
- Product number
- CS-0060033
- Product name
- 2,5-Dibromo-4-nitro-1H-imidazole
- Purity
- 99.03%
- Packaging
- 25g
- Price
- $447
- Updated
- 2021/12/16
2,5-dibromo-4-nitro-1H-imidazole Chemical Properties,Usage,Production
Description
2,5-dibromo-4-nitro-1H-imidazole is an important intermediate in the synthesis of bactericidal drug Delamanid, and 2-bromo-4-nitroimidazole (II) is also used to synthesize other nitroimidazoles under development.
Uses
2,4-Dibromo-5-nitro-1H-imidazole is an intermediate in organic synthesis and pharmaceutical intermediate, which can be used in laboratory research and development process and chemical production process.
Preparation
After reacting 4-nitroimidazole with sodium bicarbonate, bromine was added to finally obtain 2,5-dibromo-4-nitro-1H-imidazole.
Synthesis
3034-38-6
6154-30-9
The general procedure for the synthesis of 2,5-dibromo-4-nitro-1H-imidazole from 4-nitroimidazole was as follows: 4-nitroimidazole (100 g, 884 mmol), sodium bicarbonate (164 g, 1.94 mol), and water (500 ml) were mixed with vigorous stirring. Subsequently, bromine (106 ml, 2.07 mol) was added slowly and dropwise. The reaction mixture was stirred at room temperature (23°C to 25°C) for 6 h. Vigorous foaming was observed during the dropwise addition. Next, the reaction mixture was heated to 50°C to 55°C and stirring was continued for 4 hours. Upon completion of the reaction, water (400 ml) and concentrated hydrochloric acid (80 ml) were sequentially added to the mixture under ice bath cooling (temperature controlled at 10°C or lower) and stirring was continued for 1 hour. The resulting crystals were collected by filtration. The resulting crystals were first washed with 400 ml of water on filter paper, followed by two dispersion washes with 800 ml of water. Finally, the crystals were air dried at 50°C for 16 hours. A light yellow crystalline product of 213 g was obtained with a yield of 88.9%. The characteristic absorption peaks of the infrared spectrum (KBr press method) of the product were 3074, 1548, 1468, 1392, 1361, 1345, 1310, 1259, 1172, 1066, 975, 830, 667 cm-1.
References
[1] Patent: WO2005/77913, 2005, A1. Location in patent: Page/Page column 72-73
[2] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1149 - 1155
[3] Patent: EP1553088, 2005, A1. Location in patent: Page/Page column 46
[4] Patent: KR101650716, 2016, B1. Location in patent: Paragraph 0082; 0083
2,5-dibromo-4-nitro-1H-imidazole Preparation Products And Raw materials
Raw materials
Preparation Products
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