ChemicalBook > CAS DataBase List > 2,5-dibromo-4-nitro-1H-imidazole

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
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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
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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.

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N-Bromosuccinimide Price

ChemScene
Product number
CS-0060033
Product name
2,5-Dibromo-4-nitro-1H-imidazole
Purity
99.03%
Packaging
1g
Price
$52
Updated
2021/12/16
ChemScene
Product number
CS-0060033
Product name
2,5-Dibromo-4-nitro-1H-imidazole
Purity
99.03%
Packaging
250mg
Price
$53
Updated
2021/12/16
ChemScene
Product number
CS-0060033
Product name
2,5-Dibromo-4-nitro-1H-imidazole
Purity
99.03%
Packaging
10g
Price
$248
Updated
2021/12/16
ChemScene
Product number
CS-0060033
Product name
2,5-Dibromo-4-nitro-1H-imidazole
Purity
99.03%
Packaging
5g
Price
$146
Updated
2021/12/16
ChemScene
Product number
CS-0060033
Product name
2,5-Dibromo-4-nitro-1H-imidazole
Purity
99.03%
Packaging
25g
Price
$447
Updated
2021/12/16
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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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2,5-dibromo-4-nitro-1H-imidazole Suppliers

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6154-30-9, 2,5-dibromo-4-nitro-1H-imidazoleRelated Search:


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