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Safety Information

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

248.0 °F - closed cup

Flash Point(C)

120.0 °C - closed cup

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.

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

C22415-500G:4548173947990
C22415-BULK:
C22415-VAR:
C22415-10KG:
C22415-5G:4548173948003
C22415-100G:4548173947983
C22415-1KG:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0315
BCCL1975
BCCH0605
BCCJ3217
WXBC4601V

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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)
Guanidinium nitrate: a novel reagent for aryl nitrations
Ramana MMV, et al.
Tetrahedron Letters, 45(47), 8681-8683 (2004)
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)
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)
D Mortenson et al.
International endodontic journal, 45(9), 878-882 (2012-04-11)
To determine if the formation of para-chloroaniline (PCA) can be avoided by using an alternative irrigant following sodium hypochlorite but before chlorhexidine. Fifty-five single-rooted teeth were decoronated, instrumented to size 40, .06 taper whilst being irrigated with 14% ethylene-diamine-tetra-acetic acid
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