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427519

Sigma-Aldrich

2-Methylglutaronitrile

99%

Synonym(s):

α-Methylglutarodinitrile, α-Methylglutaronitrile, 1,3-Dicyanobutane, 2,4-Dicyanobutane, 2-Methylpentanedinitrile, Diacrylonitrile

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About This Item

Linear Formula:
NCCH(CH3)CH2CH2CN
CAS Number:
4553-62-2
Molecular Weight:
108.14
Beilstein/REAXYS Number:
1741955
EC Number:
224-923-5
MDL number:
MFCD00001875
UNSPSC Code:
12352100
PubChem Substance ID:
24866765
NACRES:
NA.22

Quality Level

100

assay

99%

form

liquid

impurities

<0.1% benzene

refractive index

n20/D 1.434 (lit.)

bp

269-271 °C (lit.)

mp

−45 °C (lit.)

solubility

water: soluble

density

0.95 g/mL at 25 °C (lit.)

SMILES string

CC(CCC#N)C#N

InChI

1S/C6H8N2/c1-6(5-8)3-2-4-7/h6H,2-3H2,1H3

InChI key

FPPLREPCQJZDAQ-UHFFFAOYSA-N

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General description

2-Methylglutaronitrile (MGN) is an aliphatic dinitrile. It is a high boiling solvent mainly used in the fiber industry. It is formed as a byproduct during the synthesis of adiponitrile. Synthesis of β-picoline using a mixture of 2-methylglutaronitrile and 2-ethylsuccinonitrile in the presence of silica-supported palladium, rhodium and platinum catalysts by vapour phase hydrogenation has been studied. Its core electron binding energy (CEBE) has been calculated via density functional theory (DFT). It has been reported to undergo hydrolysis catalyzed by nitrilase to form 4-cyanopentanoic acid.

Application

2-Methylglutaronitrile (MGN) may be used in the synthesis of 1,5-dimethyl-2-piperidone (1,5-DMPD) by chemoenzymatic process.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Synthesis of picolines and other aza-aromatics from arylamines by isomerization-rearrangement and from dinitriles by hydrogenation-cyclization reactions.
Prins R.
Catalysis Today, 37(2), 103-120 (1997)
Optimization of an immobilized-cell biocatalyst for production of 4-cyanopentanoic acid.
Hann EC, et al.
Organic Process Research & Development, 6(4), 492-496 (2002)
A nitrilase from a metagenomic library acts regioselectively on aliphatic dinitriles.
Bayer S, et al.
Applied Microbiology and Biotechnology, 89(1), 91-98 (2011)
D P Kelly et al.
Drug and chemical toxicology, 26(2), 99-115 (2003-06-21)
Methylglutaronitrile (MGN) is a high-boiling (263 degrees C) solvent/intermediate used in the fiber industry. Twenty male rats per group were exposed nose-only to condensation aerosol/vapor concentrations of approximately either 5, 25, or 200 mg/m3 of MGN for 6 h/day, 5
Chemoenzymatic production of 1, 5-dimethyl-2-piperidone.
Cooling FB, et al.
Journal of Molecular Catalysis. B, Enzymatic, 11(4), 295-306 (2001)
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