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141208

Sigma-Aldrich

2-Chloro-3-nitrobenzoic acid

99%

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About This Item

Linear Formula:
ClC6H3(NO2)CO2H
CAS Number:
3970-35-2
Molecular Weight:
201.56
Beilstein/REAXYS Number:
645427
EC Number:
223-590-3
MDL number:
MFCD00007069
UNSPSC Code:
12352100
PubChem Substance ID:
24848494

assay

99%

mp

183-187 °C (lit.)

SMILES string

OC(=O)c1cccc(c1Cl)[N+]([O-])=O

InChI

1S/C7H4ClNO4/c8-6-4(7(10)11)2-1-3-5(6)9(12)13/h1-3H,(H,10,11)

InChI key

JRQDVRIQJJPHEQ-UHFFFAOYSA-N

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General description

2-Chloro-3-nitrobenzoic acid undergoes condensation with aminoquinolines to yield phenylquinolylamines.

Application

2-Chloro-3-nitrobenzoic acid was used as reagent during the synthesis of new biprivileged molecular scaffolds of tetracyclic indolo-benzodiazepines and indolo-quinoxalines. It was used in a microwave-promoted Ulmann condensation with 2-aminopyridines.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317,H319

Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

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

Certificates of Analysis (COA)

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Synthetic Communications, 36, 1715-1715 (2006)
Indrajeet J Barve et al.
Chemistry, an Asian journal, 7(7), 1684-1690 (2012-04-19)
The present article describes the design and synthesis of new biprivileged molecular scaffolds with diverse structural features. Commercially available, simple heterocyclic building blocks such as 4-fluoro-3-nitrobenzoic acid, 2-chloro-3-nitrobenzoic acid, and indoline were utilized for the synthesis of the novel heterocycles.
J B Bongui et al.
Chemical & pharmaceutical bulletin, 49(9), 1077-1080 (2001-09-18)
Condensation of either 2-bromobenzoic acid (4) or 2-chloro-3-nitrobenzoic acid (5) with suitable aminoquinolines 6-8 afforded phenylquinolylamines 9-13. Acid mediated cyclization gave the corresponding 12H-benzo[b][1,7]phenanthrolin-7-ones 14 and 15, and 12H-benzo[b][1,10]phenanthrolin-7-ones 16-18. Compounds 14, 16, and 17 were subsequently N-methylated to 6-demethoxyacronycine

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