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Merck
CN

427519

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24866765
EC Number:
224-923-5
Beilstein/REAXYS Number:
1741955
MDL number:
MFCD00001875
Assay:
99%
Form:
liquid

Key Documents

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InChI key

FPPLREPCQJZDAQ-UHFFFAOYSA-N

InChI

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

SMILES string

CC(CCC#N)C#N

assay

99%

form

liquid

impurities

<0.1% benzene

Quality Level

100

bp

269-271 °C (lit.)

mp

−45 °C (lit.)

solubility

water: soluble

density

0.95 g/mL at 25 °C (lit.)

functional group

nitrile

Related Categories

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

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

239.0 °F - closed cup

flash_point_c

115 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBH5948V
MKBG2277V
MKBD3702
MKAA3172
07624KG

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Synthesis of ?-picoline from 2-methylglutaronitrile over supported noble metal catalysts II. Influence of operation parameters.
Lanini S and Prins R.
Applied Catalysis A: General, 137(2), 307-326 (1996)
Chemoenzymatic production of 1, 5-dimethyl-2-piperidone.
Cooling FB, et al.
Journal of Molecular Catalysis. B, Enzymatic, 11(4), 295-306 (2001)
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
Accurate density functional calculation of core electron binding energies: Part V: application to nitriles. Model molecules for polyacrylonitrile revisited.
Bureau C, et al.
Journal of Electron Spectroscopy and Related Phenomena, 83(2), 227-234 (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)
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