Methyl isocyanide

Base Information

• Chemical Name: Methyl isocyanide
• CAS No.: 593-75-9
• Molecular Formula: C₂H₃N
• Molecular Weight: 41.0525
• European Community (EC) Number: 209-806-9
• UNII: B5B6DXM7GG
• DSSTox Substance ID: DTXSID3075040
• Nikkaji Number: J2.698K
• Wikipedia: Methyl_isocyanide
• Wikidata: Q2435355
• Metabolomics Workbench ID: 52365
• Mol file: 593-75-9.mol

Synonyms:methyl isocyanide;methylisonitrile

Chemical Property of Methyl isocyanide

Chemical Property:

• Melting Point: -45°C
• Refractive Index: 1.3427
• Boiling Point: 81.65°C (estimate)
• PSA: 0.00000
• Density: 0.7424
• LogP: -0.23380
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Soluble), Methanol (Slightly)
• Water Solubility.: 91g/L(15 oC)
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 41.026549100
• Heavy Atom Count: 3
• Complexity: 29.3

Purity/Quality:

99%, ^*data from raw suppliers

METHYL ISOCYANIDE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]#[C-]
• Recent ClinicalTrials: Safety and Immunogenicity Evaluation After One or Two Doses of Novartis Meningococcal ACWY Conjugate Vaccine in Healthy Infants and Toddlers
• Uses: Isocyanomethane can be used as porous embolization microspheres comprising drugs.

Technology Process of Methyl isocyanide

There total 56 articles about Methyl isocyanide 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: 87.0%

2,5-diaza-3,4-dimethyl-2,4-hexadiene (4381-85-5) → N-methyl-acetamide (79-16-3) + methyl isocyanate (593-75-9,685498-28-6)

Guidance literature:

With oxygen; rose bengal; In acetonitrile; at 13 ℃; for 9h; Irradiation;

DOI:10.1021/jo00027a041

Reference yield: 87.0%

Ni2(μ-CNMe)(CNMe)2(dppm)2 + phenyl isocyanate (1197040-29-1,931-54-4) → Ni2(μ-CNC6H5)(CNMe)2(bis(diphenylphosphino)methane)2 + methyl isocyanate (593-75-9,685498-28-6)

Guidance literature:

In benzene; under N2; evapn. under vac., residue redissolved in benzene, addn. of hexane, filtered out, rinsed with acetonitrile and ether, dried under vac., recrystn. (benzene/hexane);

Reference yield: 84.0%

{Ni3(μ3-η1-methylisocyanide)(μ3-I)(methylisocyanide)2(dppm)2}I + bis-diphenylphosphinomethane (2071-20-7) → methyl isocyanate (593-75-9,685498-28-6) + {Ni3(CNCH3)I(P(C6H5)2CH2P(C6H5)2)3}(1+)*I(1-)*CH2Cl2={Ni3(CNCH3)I(P(C6H5)2CH2P(C6H5)2)3}I*CH2Cl2

Guidance literature:

In acetonitrile; addn. of the ligand (dppm) to a stirred soln. of the complex at room temp., refluxing, 36 h, with occasional purging with N2 (to remouve the volatile CNMe); vac. evapn., residue recrystn. (CH2Cl2-pentane), washed (CH3CN and Et2O), vac. dried;

DOI:10.1016/S0277-5387(00)86755-8

upstream raw materials:

diazomethane

hydrogen cyanide

potassium cyanide

potassium methyl sulfate

Downstream raw materials:

N-Chloracetyl-2,5-cyclohexadien-1-alanin-methylamid

N-Trifluoracetyl-2,5-cyclohexadien-1-alanin-methylamid

((isocyanomethyl)sulfonyl)benzene

[(p-methylphenyl)sulfonylmethyl]isonitrile

Refernces

• 1、 Blanco, Susana,Lister, David G.,Legon,Rego, Christopher A.. "Microwave spectrum and geometry of the methyl isocyanide-argon complex". . p. 1287 - 1290. Retrieved 1997.
• 2、 Knight, J. S.,Freeman, C. G.,McEwan, M. J.. "Isomers of C2H4N+ and the Proton Affinities of CH3CN and CH3NC". . p. 1404 - 1408. Retrieved 1986.
• 3、 Zhang, Stephanie J.,Duzdevich, Daniel,Szostak, Jack W.. "Potentially prebiotic activation chemistry compatible with nonenzymatic RNA copying". . p. 14810 - 14813. Retrieved 2020.
• 4、 Ratliff, Kevin S.,Fanwick, Phillip E.,Kubiak, Clifford P.. "". . p. 1487 - 1490. Retrieved 1990.
• 5、 Mariani, Angelica,Russell, David A.,Javelle, Thomas,Sutherland, John D.. "A Light-Releasable Potentially Prebiotic Nucleotide Activating Agent". supporting information. p. 8657 - 8661. Retrieved 2018/07/15.