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269050

Sigma-Aldrich

5-Chloro-2-nitroaniline

97%

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Synonym(s):
2-Amino-4-chloro-nitrobenzene
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.)

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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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