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234486

Sigma-Aldrich

3-(Dimethylamino)propionitrile

98%

Synonym(s):

DMAPN

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About This Item

Linear Formula:
(CH3)2NCH2CH2CN
CAS Number:
1738-25-6
Molecular Weight:
98.15
Beilstein:
773779
EC Number:
217-090-4
MDL number:
MFCD00001957
UNSPSC Code:
12352100
PubChem Substance ID:
24854044
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.426 (lit.)

bp

171 °C/750 mmHg (lit.)

mp

−43 °C (lit.)

density

0.87 g/mL at 25 °C (lit.)

SMILES string

CN(C)CCC#N

InChI

1S/C5H10N2/c1-7(2)5-3-4-6/h3,5H2,1-2H3

InChI key

MTPJEFOSTIKRSS-UHFFFAOYSA-N

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General description

Hydrogenation of 3-(dimethylamino)propionitrile over palladium catalysts has been investigated.

Application

3-(Dimethylamino)propionitrile has been used:
  • to initiate the organic polymerization during the synthesis of class I hybrid poly(N-isopropylacrylamide)/silica hydrogels
  • in preparation of cysteine modifying agents based on the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide (4-DMN)
Catalyst similar to TEMED used to form oxygen free radicals from ammonium persulfate. Free radicals cause acrylamide and bis-acrylamide to polymerize.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312,H319

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

145.4 °F - closed cup

Flash Point(C)

63 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Hydrogenation of 3-(dimethylamino) propionitrile over palladium catalysts.
Krupka J, et al.
Collection of Czechoslovak Chemical Communications, 65(11), 1805-1819 (2000)
Galen Loving et al.
Bioconjugate chemistry, 20(11), 2133-2141 (2009-10-14)
The solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide (4-DMN) possesses extremely sensitive emission properties due largely to the low intrinsic fluorescence it exhibits in polar protic solvents such as water. This makes it well suited as a probe for the detection of a wide
P Banet et al.
The journal of physical chemistry. B, 113(45), 14914-14919 (2009-11-06)
Class I hybrid poly(N-isopropylacrylamide)/silica hydrogels, PNIPAM/SiO2, were prepared by a new one shot synthesis. In this approach, the free-radical polymerization of vinyl groups of N-isopropylacrylamide (NIPAM) and the hydrolysis-condensation of alkoxy groups of tetramethoxysilane (TMOS) are performed concomitantly using sodium
Inhibition of acetylcholinesterase by neurotoxic aminonitriles.
J R Froines
Biochemical pharmacology, 34(17), 3185-3187 (1985-09-01)
J R Froines et al.
Journal of toxicology and environmental health, 16(3-4), 469-479 (1985-01-01)
The neurotoxic aminonitrile dimethylaminopropionitrile (DMAPN) inhibits the crystalline glycolytic enzymes glyceraldehyde-3-phosphate dehydrogenase (GAPDH) and fructose-6-phosphate kinase (phosphofructokinase, PFK). Preincubation of GAPDH with the aminonitrile enhances the inhibition, indicating that the inhibition is irreversible. The overall bimolecular rate constant ki was
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