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Sigma-Aldrich

4-Bromo-1,2-diaminobenzene

97%

Synonym(s):

4-Bromo-2-aminoaniline, 4-Bromo-o-phenylenediamine

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About This Item

Empirical Formula (Hill Notation):
C6H7BrN2
CAS Number:
1575-37-7
Molecular Weight:
187.04
MDL number:
MFCD02660622
UNSPSC Code:
12352100
PubChem Substance ID:
24883092
NACRES:
NA.22

assay

97%

form

solid

mp

65-69 °C (dec.) (lit.)

SMILES string

Nc1ccc(Br)cc1N

InChI

1S/C6H7BrN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2

InChI key

WIHHVKUARKTSBU-UHFFFAOYSA-N

General description

4-Bromo-1,2-diaminobenzene can be obtained from 1,2-diaminobenzene via acetylation followed by bromination and alkaline hydrolysis.

4-Bromo-1,2-diaminobenzene is used as a precursor in the production of tetra-dentate unsymmetrical Schiff base.

Application

4-Bromo-1,2-diaminobenzene can be used as a precursor for preparing fluorescent dipolar quinoxaline derivatives, which can find applications as potential emissive and electron-transport materials. It can also be used in the synthesis of 6-bromo-2-methylbenzimidazole.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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"Guanidine chemistry"
Ishikawa T, et al.
Chemical & Pharmaceutical Bulletin, 58(12), 1555-1564 (2010)
"The synthesis and characterization of novel dipolar fluorescent materials based on a quinoxaline core"
Wang H, et al.
Dyes and Pigments, 83(03), 269-275 (2009)
"A PdII Complex Bearing a Benzimidazole-Derived Ligand with Potentially ?Mesoionic and Remote? Character and Its Catalytic Activity"
Huynh VH, et al.
European Journal of Organic Chemistry, 2013(26), 4654-4661 (2013)
Erin Wachter et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 22(2), 550-559 (2015-11-13)
Recognition and regulation of G-quadruplex nucleic acid structures is an important goal for the development of chemical tools and medicinal agents. The addition of a bromo-substituent to the dipyridylphenazine (dppz) ligands in the photophysical "light switch", [Ru(bpy)2 dppz](2+) , and
Jacek E Nycz et al.
Molecules (Basel, Switzerland), 24(22) (2019-11-27)
New approaches to the synthesis of 4,7-dichloro-1,10-phenanthrolines and their corresponding 9H-carbazol-9-yl-, 10H-phenothiazin-10-yl- and pyrrolidin-1-yl derivatives were developed. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, electronic absorption spectroscopy and multinuclear NMR in both solution

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