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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.)

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

269050-VAR:
269050-BULK:
269050-10KG:
269050-5G:
269050-25G:
269050-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
S47299
09913BH
02102BH
02931TP
01323LM

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Sigma-Aldrich

108871

4-Chloro-o-phenylenediamine

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
Traceless solid-phase synthesis of 5-benzoylbenzimidazoles.
Canadian Journal of Chemistry, 79(11), 1556-1561 (2001)

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