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405280

Sigma-Aldrich

2-Amino-4-chlorobenzonitrile

99%

Synonym(s):

4-Chloroanthranilonitrile, 5-Chloro-2-cyanoaniline

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About This Item

Linear Formula:
H2NC6H3(Cl)CN
CAS Number:
38487-86-4
Molecular Weight:
152.58
Beilstein:
2085559
EC Number:
253-967-8
MDL number:
MFCD00035927
UNSPSC Code:
12352100
PubChem Substance ID:
24865306
NACRES:
NA.22

Quality Level

100

Assay

99%

form

powder

mp

157-162 °C (lit.)

functional group

chloro
nitrile

SMILES string

Nc1cc(Cl)ccc1C#N

InChI

1S/C7H5ClN2/c8-6-2-1-5(4-9)7(10)3-6/h1-3H,10H2

InChI key

UZHALXIAWJOLLR-UHFFFAOYSA-N

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General description

2-Amino-4-chlorobenzonitrile (2A4CBN) is a benzonitrile derivative. A study of the molecular structure, vibrational spectra and NBO analysis of 2A4CBN has been undertaken. Transformation of 2A4CBN into quinazoline-2,4(1H,3H)-diones at atmospheric pressure of CO2 in the presence of monomeric tungstate, TBA2[WO4] (TBA = tetra-n-butylammonium) has been reported.

Application

2-Amino-4-chlorobenzonitrile may be used in the preparation of the following:
  • 6-chloro-4-(1-diethylamino-4-pentylamino)-2-(p-methoxyphenyl)-quinazoline dihydrochloride
  • 7-chloro-4-(1-diethylamino-4-pentylamino)-2-(p-methoxyphenyl)-quinazoline dihydrochloride
  • 4,7-dichloro-2-(2-methylprop-1-enyl)-6-nitroquinazoline
  • 6-chlorotacrine
  • N-(2-chloro-5-cyanophenyl)-4,4,4-trifluorobutanamide

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBN3026V
MKBL2213V
MKBC6108V
MKBC1978V
MKBC6108

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6-(and 7-)-Chloro-4-(1-diethylamino-4-pentylamino)-2-(p-methoxyphenyl)-quinazoline Dihydrochlorides.
McKee RL, et al.
Journal of the American Chemical Society, 69(4), 940-942 (1947)
Regioselective Suzuki-Miyaura reaction: application to the microwave-promoted synthesis of 4,7-diarylquinazolines
Kabri, Y.; et al.
Molecules (Basel), 15(5), 2949-2961 (2010)
N-(2-Chloro-5-cyanophenyl)-4,4,4-trifluorobutanamide.
Manojkumar KE, et al.
Molbank, 2013(3), M803-M803 (2013)
FT-IR and FT-Raman spectra, vibrational assignments, NBO analysis and DFT calculations of 2-amino-4-chlorobenzonitrile.
Sudha S, et al.
Journal of Molecular Structure, 958(2), 148-156 (2011)
A novel hybrid of 6-chlorotacrine and metal-amyloid-β modulator for inhibition of acetylcholinesterase and metal-induced amyloid-β aggregation.
Kochi A, et al.
Chemical Science, 4(11), 4137-4145 (2013)
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