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478695

4-Bromo-1H-imidazole

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About This Item

Empirical Formula (Hill Notation):
C3H3BrN2
CAS Number:
2302-25-2
Molecular Weight:
146.97
NACRES:
NA.22
PubChem Substance ID:
24871567
UNSPSC Code:
12352100
MDL number:
MFCD00047021
Assay:
97%
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assay

97%

mp

131-135 °C (lit.)

functional group

bromo

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:
  • 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

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR1814V
MKBD7183V
MKBD7183
09907DJ
01528KH

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Palladium-catalyzed amination of unprotected five-membered heterocyclic bromides.
Su M, et al.
Organic Letters, 16(3), 832-835 (2014)
Crystal structure of 4-bromo-1H-imidazole, at 200 K, C3H3BrN2.
Hosten EC and Betz R.
Zeitschrift fur Kristallographie, 230(1), 27-28 (2015)
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)
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Global Trade Item Number

SKUGTIN
478695-1G04061825754321