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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:
1741955
EC Number:
224-923-5
MDL number:
MFCD00001875
UNSPSC Code:
12352100
PubChem Substance ID:
24866765
NACRES:
NA.22
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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.)

functional group

nitrile

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.[1] It is formed as a byproduct during the synthesis of adiponitrile.[2] 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.[3] Its core electron binding energy (CEBE) has been calculated via density functional theory (DFT).[4] It has been reported to undergo hydrolysis catalyzed by nitrilase to form 4-cyanopentanoic acid.[5][6]

Application

2-Methylglutaronitrile (MGN) may be used in the synthesis of 1,5-dimethyl-2-piperidone (1,5-DMPD) by chemoenzymatic process.[7]

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311,H330

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)
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)
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
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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