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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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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
Comparative chemical mutagenesis; well designed and well assessed. Comparative genetic toxicology: the second UK EMS Collaborative Study.
F H Sobels
Mutation research, 157(2-3), 107-110 (1985-08-01)
Rômulo A Ando et al.
Physical chemistry chemical physics : PCCP, 19(36), 25151-25157 (2017-09-09)
In this work we demonstrate the use of the push-pull model system 4-(dimethylamino)benzonitrile (DMABN) as a convenient molecular probe to investigate the local solvation structure and dynamics by means of time-resolved infrared spectroscopy (TRIR). The photochemical features associated with this
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
The formation of a novel mercapturic acid during the metabolism of an N-methyl aromatic amine, 4-cyano-N,N-dimethylaniline.
C J Logan et al.
Biochemical pharmacology, 33(14), 2345-2346 (1984-07-15)
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