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523364

Sigma-Aldrich

2-Bromo-3-nitropyridine

98%

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About This Item

Empirical Formula (Hill Notation):
C5H3BrN2O2
CAS Number:
19755-53-4
Molecular Weight:
202.99
MDL number:
MFCD00955613
UNSPSC Code:
12352100
PubChem Substance ID:
24874331
NACRES:
NA.22

assay

98%

form

solid

mp

122-125 °C (lit.)

functional group

bromo
nitro

SMILES string

[O-][N+](=O)c1cccnc1Br

InChI

1S/C5H3BrN2O2/c6-5-4(8(9)10)2-1-3-7-5/h1-3H

InChI key

ZCCUFLITCDHRMG-UHFFFAOYSA-N

General description

2-Bromo-3-nitropyridine is a pyridine derivative. It can be synthesized from 3-nitropyridine-2-amine.[1]

application

2-Bromo-3-nitropyridine may be used in the synthesis of the following:
  • 3-nitropyridine-2-carbonitrile[1]
  • pyrrolo[3,2-b]pyridine[2]
  • 3-(hetero)arylated phenothiazines[3]
  • 7-anilino-6-azaindole-1-benznesulfonamides[4]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
12928CE
10820JD
17012PO
03325BC
09312MO

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Condensed heteroaromatic ring systems. XII. Synthesis of indole derivatives from ethyl 2-bromocarbanilates.
Sakamoto T, et al.
Chemical & Pharmaceutical Bulletin, 35(5), 1823-1828 (1987)
Hsueh-Yun Lee et al.
Journal of medicinal chemistry, 56(20), 8008-8018 (2013-10-11)
Preliminary biological data on 7-anilino-6-azaindoles (8-11) suggested that hydrophobic substituents at C7 contribute to enhancement of antiproliferative activity. A novel series of 7-aryl-6-azaindole-1-benzenesulfonamides (12-22) were developed and showed improved cytotoxicity compared to ABT751 (5). The conversion of C7 phenyl rings
Yvonnick Loidreau et al.
European journal of medicinal chemistry, 58, 171-183 (2012-11-06)
A useful and rapid access to libraries of N-arylbenzo[b]thieno[3,2-d]pyrimidin-4-amines and their pyrido and pyrazino analogues was designed and optimized for the first time via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with N'-(2-cyanoaryl)-N,N-dimethylformimidamides obtained by reaction of thiophene
Synthesis and Electronic Properties of 3-Acceptor-Substituted and 3, 7-Bisacceptor-Substituted Phenothiazines.
Sailer M, et al.
European Journal of Organic Chemistry, 2006(2), 423-435 (2006)

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