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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

Signal Word

Danger

Hazard Statements

H301,H315,H317,H319

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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"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
2, 2?-[5-Bromo-o-phenylenebis (nitrilomethylidyne)] diphenol
Gao J and Cheng Y
Acta Crystallographica Section E, Structure Reports Online, 65(5), o979-o979 (2009)
"Guanidine chemistry"
Ishikawa T, et al.
Chemical & Pharmaceutical Bulletin, 58(12), 1555-1564 (2010)

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