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C22415

Sigma-Aldrich

4-Chloroaniline

98%

Synonym(s):

1-Amino-4-chlorobenzene, 4-Chlorophenylamine, p-Chloroaniline

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About This Item

Linear Formula:
ClC6H4NH2
CAS Number:
106-47-8
Molecular Weight:
127.57
Beilstein:
471359
EC Number:
203-401-0
MDL number:
MFCD00007835
UNSPSC Code:
12352100
PubChem Substance ID:
24892480
NACRES:
NA.22

vapor density

4.4 (vs air)

Quality Level

200

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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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.

Signal Word

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

WGK

WGK 3

Flash Point(F)

248.0 °F

Flash Point(C)

120.0 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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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)
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)
Kun Yang et al.
Environmental science & technology, 42(21), 7931-7936 (2008-11-27)
Aqueous adsorption of a series of phenols and anilines by a multiwalled carbon nanotube material (MWCNT15), which depends strongly on the solution pH and the number and types of solute groups, was investigated in this study. The pH-dependent adsorption coefficients
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