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C22415

Sigma-Aldrich

4-Chloroaniline

98%

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Synonym(s):
1-Amino-4-chlorobenzene, 4-Chlorophenylamine, p-Chloroaniline
Linear Formula:
ClC6H4NH2
CAS Number:
Molecular Weight:
127.57
Beilstein/REAXYS Number:
471359
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

4.4 (vs air)

Quality Level

vapor pressure

0.15 mmHg ( 25 °C)

assay

98%

form

chips
crystals or chunks

bp

232 °C (lit.)

mp

67-70 °C (lit.)

SMILES string

Nc1ccc(Cl)cc1

InChI

1S/C6H6ClN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2

InChI key

QSNSCYSYFYORTR-UHFFFAOYSA-N

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1 of 4

This Item
PHR12001522778.02613
4-Chloroaniline 98%

C22415

4-Chloroaniline

p-Chloroaniline Pharmaceutical Secondary Standard; Certified Reference Material

PHR1200

p-Chloroaniline

4-Chlorophenyl isocyanate 98%

152277

4-Chlorophenyl isocyanate

4-Chloroaniline for synthesis

8.02613

4-Chloroaniline

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

bp

232 °C (lit.)

bp

232 °C (lit.)

bp

203-204 °C (lit.)

bp

232 °C/1013 hPa

mp

67-70 °C (lit.)

mp

67-70 °C (lit.)

mp

26-29 °C (lit.)

mp

66-69 °C

form

chips, crystals or chunks

form

-

form

solid

form

solid

vapor density

4.4 (vs air)

vapor density

4.4 (vs air)

vapor density

-

vapor density

-

Application

4-Chloroaniline can undergo:
  • Allylation in the presence of ultrasonication to form N-allyl-4-chloroaniline, a precursor for bioactive compounds containing indole and dihydroindole nucleus.
  • Povarov reaction with cyclopentadiene to form C-2 aliphatic substituted tetrahydroquinolines.
  • Mannich reaction with aldehydes and cyclic ketones to form β-amino carbonyl compounds.
  • Nitration to form 4-chloro-3-nitroaniline in the presence of guanidinium nitrate.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Skin Sens. 1

Storage Class

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

wgk_germany

WGK 3

flash_point_f

248.0 °F - closed cup

flash_point_c

120.0 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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4-CHLOROPHENYLUREA AldrichCPR

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Highly efficient one-pot, three-component Mannich reaction catalysed by boric acid and glycerol in water with major `syn?diastereoselectivity
Mukhopadhyay C, et al.
Tetrahedron Letters, 50(29), 4246-4250 (2009)
Guanidinium nitrate: a novel reagent for aryl nitrations
Ramana MMV, et al.
Tetrahedron Letters, 45(47), 8681-8683 (2004)
Factorial study to assess an ultrasonic methodology for the allylation of 4-chloroaniline
Nascimento LFS and Fernandes JPS
Green Processing and Synthesis, 6(2), 203-209 (2017)
Lanthanide (III)-catalyzed multi-component aza-Diels-Alder reaction of aliphatic N-arylaldimines with cyclopentadiene.
Powell DA and Batey RA.
Tetrahedron Letters, 44(41), 7569-7573 (2003)
John E Thomas et al.
Journal of endodontics, 36(2), 315-317 (2010-02-02)
The purpose of this in vitro study was to determine whether para-chloroaniline (PCA) is formed through the reaction of mixing sodium hypochlorite (NaOCl) and chlorhexidine (CHX). Initially, commercially available samples of chlorhexidine acetate (CHXa) and PCA were analyzed with 1H

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