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D139505

Sigma-Aldrich

4-(Dimethylamino)benzonitrile

98%

Synonym(s):

4-Cyano-N,N-dimethylaniline, DMABN

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About This Item

Linear Formula:
(CH3)2NC6H4CN
CAS Number:
1197-19-9
Molecular Weight:
146.19
Beilstein:
971606
EC Number:
214-819-8
MDL number:
MFCD00001815
UNSPSC Code:
12352100
PubChem Substance ID:
24893427
NACRES:
NA.22

Assay

98%

form

crystals

bp

318 °C (lit.)

mp

72-75 °C (lit.)

SMILES string

CN(C)c1ccc(cc1)C#N

InChI

1S/C9H10N2/c1-11(2)9-5-3-8(7-10)4-6-9/h3-6H,1-2H3

InChI key

JYMNQRQQBJIMCV-UHFFFAOYSA-N

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General description

4-(Dimethylamino)benzonitrile is extensively used in photophysical studies due to its ability to undergo intramolecular charge transfer (ICT) from the dimethylamino moiety to the cyanophenyl moiety on photo-excitation leading to the appearance of dual fluorescence.

Application

4-(Dimethylamino)benzonitrile can be used in the synthesis of 3,6-diphenyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione derivatives.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H317,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Sigma-Aldrich

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Sigma-Aldrich

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D Hesk et al.
Xenobiotica; the fate of foreign compounds in biological systems, 18(8), 955-966 (1988-08-01)
1. The metabolic fate of 4-cyanoacetanilide (CAA), labelled with 14C and 13C in the N-acetyl group, was studied in rats (oral dose, 22.5 mg/kg) and mice (oral dose 21.7 mg/kg). 2. The metabolic profile in the urine of rats was
Do fluorescence and transient absorption probe the same intramolecular charge transfer state of 4-(dimethylamino) benzonitrile?
Gustavsson T, et al.
J. Chem. Phys. , 131, 031101-031101 (2009)
D H Hutson et al.
Xenobiotica; the fate of foreign compounds in biological systems, 14(12), 925-934 (1984-12-01)
4-Cyano-N,N-dimethylaniline (CDA), when administered to rats as a single oral dose (18.5 mg/kg), was rapidly absorbed and eliminated as a mixture of metabolites in the urine (86% dose after 24 h). Residues in tissues after 48 h, expressed as microgram
Novel, soluble diphenyl-diketo-pyrrolopyrroles: Experimental and theoretical study.
Vala M, et al.
Dyes and Pigments, 84(2), 176-182 (2010)
F K Ennever et al.
Mutagenesis, 1(2), 119-123 (1986-03-01)
The carcinogenicity prediction and battery selection (CPBS) procedure was used to analyze the short-term in vitro and in vivo genotoxicity results obtained during the Second UKEMS Collaborative Study. In accordance with preliminary animal bioassay results, CPBS predicted correctly the carcinogenicity
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