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About This Item
Empirical Formula (Hill Notation):
C3H3BrN2
CAS Number:
Molecular Weight:
146.97
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay
97%
mp
131-135 °C (lit.)
SMILES string
Brc1c[nH]cn1
InChI
1S/C3H3BrN2/c4-3-1-5-2-6-3/h1-2H,(H,5,6)
InChI key
FHZALEJIENDROK-UHFFFAOYSA-N
General description
4-Bromo-1H-imidazole (4-Br-1H-Im) is a heterocyclic building block containing an imidazole ring. It crystallizes in the monoclinic space group P21/c.
Application
4-Bromo-1H-imidazole may be used as a starting material to prepare 5(4)-bromo-4(5)-nitroimidazole.
It may be used in the synthesis of the following aminoimidazoles via palladium catalyzed amination:
It may be used in the synthesis of the following aminoimidazoles via palladium catalyzed amination:
- N-(4-ethoxyphenyl)-1H-imidazol-4-amine
- N-(2,5-dimethoxyphenyl)-1H-imidazol-4-amine
- N-(3-phenoxyphenyl)-1H-imidazol-4-amine
- N-(4-cyanophenyl)-1H-imidazol-4-amine
- N-(pyridin-3-yl)-1H-imidazol-4-amine
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Crystal structure of 4-bromo-1H-imidazole, at 200 K, C3H3BrN2.
Hosten EC and Betz R.
Zeitschrift fur Kristallographie, 230(1), 27-28 (2015)
Palladium-catalyzed amination of unprotected five-membered heterocyclic bromides.
Su M, et al.
Organic Letters, 16(3), 832-835 (2014)
Efficient synthesis of DNA containing the guanine oxidation-nitration product 5-guanidino-4-nitroimidazole: Generation by a postsynthetic substitution reaction.
Neeley WL, et al.
Organic Letters, 6(2), 245-248 (2004)
Guokai Cui et al.
Chemistry, an Asian journal, 12(21), 2863-2872 (2017-08-26)
A new strategy involving the computer-assisted design of substituted imidazolate-based ionic liquids (ILs) through tuning the absorption enthalpy as well as the basicity of the ILs to improve SO
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