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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

Quality Level

200

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL2122
0000267749
BCCH3591
BCCG8742
BCCG8167

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Sigma-Aldrich

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Sigma-Aldrich

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Mohammed H Ahmed et al.
The journal of adhesive dentistry, 21(2), 117-132 (2019-04-06)
Universal adhesives use a combined primer/bonding resin applied either in 2-step etch-and-rinse (2-E&R) or 1-step self-etch (1-SE) mode. This study investigated whether three universal adhesives would benefit from an extra bonding layer (EBL), essentially making them 3-step E&R (3-E&R) and
Victor A Galievsky et al.
The journal of physical chemistry. A, 115(40), 10823-10845 (2011-08-02)
The excited state behavior of the six m,n-dicyano-N,N-dimethylanilines (mnDCDMA) and m,n-dicyano-(N-methyl-N-isopropyl)anilines (mnDCMIA) is discussed as a function of solvent polarity and temperature. The dicyano moiety in these electron donor (D)/acceptor (A) molecules has a considerably larger electron affinity than the
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
D A Ryan et al.
Journal of pharmaceutical and biomedical analysis, 13(6), 735-745 (1995-05-01)
The structure of two biliary metabolites of 4-cyano-N,N-dimethyl aniline (CDA) contained in whole rat bile have been studied in detail by NMR at 400 MHz. A 4-cyano-N-methyl glutathione-N-aniline conjugate was identified as a biliary metabolite of CDA using relatively simple
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
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