2-Methyleneglutaronitrile

Base Information

• Chemical Name: 2-Methyleneglutaronitrile
• CAS No.: 1572-52-7
• Molecular Formula: C6H6N2
• Molecular Weight: 106.127
• Hs Code.: 2926909090
• European Community (EC) Number: 216-391-8
• UNII: 0Y85F7Y2B8
• DSSTox Substance ID: DTXSID2027418
• Nikkaji Number: J27.805J
• Wikipedia: 2-Methyleneglutaronitrile
• Wikidata: Q27888909
• ChEMBL ID: CHEMBL3182918
• Mol file: 1572-52-7.mol

Synonyms:Glutaronitrile,2-methylene- (7CI,8CI);2,4-Dicyano-1-butene;2-Methyleneglutarodinitrile;2-Methylenepentanedinitrile;a-Methyleneglutarodinitrile;a-Methyleneglutaronitrile;

Chemical Property of 2-Methyleneglutaronitrile

Chemical Property:

• Vapor Pressure: 0.00439mmHg at 25°C
• Melting Point: -9.6 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)
• Boiling Point: 277.9 °C at 760 mmHg
• Flash Point: 137.9 °C
• PSA: 47.58000
• Density: 0.971 g/cm³
• LogP: 1.36996
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 106.053098200
• Heavy Atom Count: 8
• Complexity: 173

Purity/Quality:

≥99% ^*data from raw suppliers

2-Methylenepentanedinitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C(CCC#N)C#N
• Uses: Vinyl monomer for polymerization and copoly-merization, intermediate in making fibers and phar-maceuticals.

Technology Process of 2-Methyleneglutaronitrile

There total 9 articles about 2-Methyleneglutaronitrile 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: 90.7%

acrylonitrile (107-13-1,25014-41-9) → 2,4-dicyano-1-butene (1572-52-7)

Guidance literature:

With 1-ethyl-3-methylimidazolium tetrafluoroborate; hydroquinone; triphenylphosphine; at 50 ℃; for 24h; Time; Temperature; Inert atmosphere;

Reference yield: 65.0%

acrylonitrile (107-13-1,25014-41-9) → 4-cyano-2-methyleneheptane-1,7-dinitrile (1572-51-6) + 2,4-dicyano-1-butene (1572-52-7)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; at 36 ℃; for 23h; under 3000240 Torr;

Reference yield: 10.0%

acrylonitrile (107-13-1,25014-41-9) + 3,3-Dimethylcyclopropen (3907-06-0) → 2,4-dicyano-1-butene (1572-52-7) + 3,3,6,6-Tetramethyl-trans-tricyclo<3.1.0.02,4>hexan (58987-01-2) + (1R,2R,4S,5S,7R)-3,3,8,8-Tetramethyl-tricyclo[5.1.0.02,4]octane-5-carbonitrile (103667-10-3) + (1R,2R,4S,5R,7R)-3,3,8,8-Tetramethyl-tricyclo[5.1.0.02,4]octane-5-carbonitrile (103620-08-2) + (Z)-3-((1S,2R)-3,3,2',2'-Tetramethyl-bicyclopropyl-2-yl)-acrylonitrile (103620-06-0) + (E)-3-((1S,2R)-3,3,2',2'-Tetramethyl-bicyclopropyl-2-yl)-acrylonitrile (103620-07-1)

Guidance literature:

bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tert-Butyldiisopropylphosphan; In toluene; at 50 ℃; for 10h; Product distribution; var. of cocatalyst;

upstream raw materials:

4-Hydroxyiminomithyl-pent-4-ennitril

acrylonitrile

1,2-Dibromo-2,4-dicyanobutane

3,3-Dimethylcyclopropen

Downstream raw materials:

1-(5-Nitro-2-trifluoromethylphenyl)-2-chloro-2,4-dicyanobutane

1-(3-Trifluoromethylphenyl)-2-chloro-2,4-dicyanobutane

1-(3,4-Dichlorophenyl)-2-chloro-2,4-dicyanobutane

γ-Cyanopimelonitrile

Refernces

• 1、 Saegusa et al.. "". . p. 877. Retrieved 1970.
• 2、 Yu, Lei,Wang, Jun,Zhang, Xu,Cao, Hongen,Wang, Genlin,Ding, Kehong,Xu, Qing,Lautens, Mark. "Practical and scalable preparation of 2-methyleneglutaronitrile via an efficient and highly selective head-to-tail dimerization of acrylonitrile catalysed by low-loading of tricyclohexylphosphine". . p. 19122 - 19126. Retrieved 2014.
• 3、 -. "Acrylonitrile dimerization preparation 2-methylene-glutaronitrile (MGN) method (by machine translation)". Paragraph 0012; 0013. . Retrieved 2017/06/03.