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269050

Sigma-Aldrich

5-Chloro-2-nitroaniline

97%

Synonym(s):

2-Amino-4-chloro-nitrobenzene

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About This Item

Linear Formula:
ClC6H3(NO2)NH2
CAS Number:
1635-61-6
Molecular Weight:
172.57
Beilstein:
2210201
EC Number:
216-661-5
MDL number:
MFCD00007776
UNSPSC Code:
12352100
PubChem Substance ID:
24856308
NACRES:
NA.22

Quality Level

100

Assay

97%

form

chunks

mp

125-129 °C (dec.) (lit.)

functional group

chloro

SMILES string

Nc1cc(Cl)ccc1[N+]([O-])=O

InChI

1S/C6H5ClN2O2/c7-4-1-2-6(9(10)11)5(8)3-4/h1-3H,8H2

InChI key

ZCWXYZBQDNFULS-UHFFFAOYSA-N

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General description

The coupling of divinylbenzene cross-linked polystyrene with 5-chloro-2-nitroaniline followed by oxidative decyanation afforded benzophenone.

Application

5-Chloro-2-nitroaniline was used in the synthesis of 5-(4-substituted piperazin-1-yl)-2-nitroanilines and 5-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Chronic 2 - STOT RE 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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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Sigma-Aldrich

108871

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Traceless solid-phase synthesis of 5-benzoylbenzimidazoles.
Canadian Journal of Chemistry, 79(11), 1556-1561 (2001)
R M Sánchez-Alonso et al.
Die Pharmazie, 44(9), 606-607 (1989-09-01)
A series of 5-(4-substituted piperazin-1-yl)-2-nitroanilines (4) and 5-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates (6) has been synthesized starting from 5-chloro-2-nitroaniline (3) and N-monosubstituted piperazines. Catalytic reduction of 4 with Pd/C followed by treatment with 1,3-dicarbomethoxy-S-methylisothiourea yielded the corresponding methyl-5-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates (6) which were for

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