2-Methylglutaronitrile

Base Information

• Chemical Name: 2-Methylglutaronitrile
• CAS No.: 4553-62-2
• Molecular Formula: C6H8 N2
• Molecular Weight: 108.143
• Hs Code.: 2926909090
• European Community (EC) Number: 224-923-5
• UN Number: 3276
• UNII: EJX3MSL725
• DSSTox Substance ID: DTXSID4025612
• Nikkaji Number: J14.515G
• Wikipedia: 2-Methylglutaronitrile
• Wikidata: Q25385993
• ChEMBL ID: CHEMBL1414319
• Mol file: 4553-62-2.mol

Synonyms:methylglutaronitrile;MGN cpd

Chemical Property of 2-Methylglutaronitrile

Chemical Property:

• Appearance/Colour: Clear liquid
• Vapor Pressure: 0.0122mmHg at 25°C
• Melting Point: -45 C
• Refractive Index: n20/D 1.434(lit.)
• Boiling Point: 274 C
• Flash Point: 126 C
• PSA: 47.58000
• Density: 0.942 g/cm³
• LogP: 1.44986
• Storage Temp.: Store at +2°C to +8°C.
• Solubility.: water: soluble
• Water Solubility.: 52.3g/L at 20℃
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 108.068748264
• Heavy Atom Count: 8
• Complexity: 142
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

2-Methylglutaronitrile >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,T
• Statements: 20/21/22-23/25-21
• Safety Statements: 36/37-45-36/37/39

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC(CCC#N)C#N
• Recent ClinicalTrials: A Phase I Study to Assess Cardiac and General Safety and Pharmacokinetics of 60 mg MGN1703
• Uses: 2-Methylglutaronitrile (MGN) may be used in the synthesis of 1,5-dimethyl-2-piperidone (1,5-DMPD) by chemoenzymatic process.

Technology Process of 2-Methylglutaronitrile

There total 34 articles about 2-Methylglutaronitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

4-bromovalero-nitrile (14470-12-3) + tetra-n-butylammonium cyanide (10442-39-4) → 2-methylglutaronitrile (4553-62-2)

Guidance literature:

With copper(l) iodide; In acetonitrile; at 20 ℃; for 24h; Inert atmosphere; UV-irradiation;

DOI:10.1021/jacs.5b08452

Reference yield:

hydrogen cyanide (74-90-8) + cis-2-pentenenitrile (25899-50-7) + 2-pentenenitrile (26294-98-4) + 3-Pentenenitrile (16529-66-1) + tiglonitrile (30574-97-1) + 4-Pentenenitrile (592-51-8) + (Z)-pent-2-enenitrile (16545-78-1) → pentanonitrile (110-59-8) + hexanedinitrile (111-69-3) + 2-methylglutaronitrile (4553-62-2) + 4-ethenylcyclohexene (100-40-3)

Guidance literature:

C₄₈H₅₂O₄P₂; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite; zinc(II) chloride; Product distribution / selectivity;

Reference yield:

(Z)-2-Butene (590-18-1) + hydrogen cyanide (74-90-8) + hexanedinitrile (111-69-3) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → cis-2-pentenenitrile (25899-50-7) + 2-pentenenitrile (26294-98-4) + 3-Pentenenitrile (16529-66-1) + (Z)-2-methyl-2-butenenitrile (20068-02-4) + tiglonitrile (30574-97-1) + 4-Pentenenitrile (592-51-8) + 2-METHYL-3-BUTENENITRILE (16529-56-9) + 2-methylglutaronitrile (4553-62-2) + 4-ethenylcyclohexene (100-40-3) + (Z)-pent-2-enenitrile (16545-78-1)

Guidance literature:

(Z)-2-Butene; hydrogen cyanide; hexanedinitrile; buta-1,3-diene; C₄₂H₄₀O₆P₂; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite; at 99.84 ℃;

nickel; at 109.84 ℃; Product distribution / selectivity;

upstream raw materials:

hydrogen cyanide

3-pentenenitrile

1,3-dichlorobutane

sodium cyanide

Downstream raw materials:

2-methylcadaverine

2-methylglutaric acid

3-Methylpyridine

3-Methylpiperidine