2-Cyanoethylene oxide

Base Information

• Chemical Name: 2-Cyanoethylene oxide
• CAS No.: 4538-51-6
• Molecular Formula: C3H3NO
• Molecular Weight: 69.0629
• Hs Code.: 2926909090
• European Community (EC) Number: 224-887-0
• UNII: 0C17IZ13QV
• DSSTox Substance ID: DTXSID10963379
• Nikkaji Number: J122.449B
• Wikidata: Q27236592
• Mol file: 4538-51-6.mol

Synonyms:2-cyanoethylene oxide;acrylonitrile epoxide;cyanoethylene-epoxide;glycidonitrile

Chemical Property of 2-Cyanoethylene oxide

Chemical Property:

• Vapor Pressure: 0.608mmHg at 25°C
• Boiling Point: 188.1°C at 760 mmHg
• Flash Point: 75.1°C
• PSA: 36.32000
• Density: 1.16g/cm³
• LogP: -0.09122
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 69.021463719
• Heavy Atom Count: 5
• Complexity: 80.1

Purity/Quality:

98%Min ^*data from raw suppliers

2-Cyanoethylene oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)C#N
• Uses: A putative toxic and carcinogenic metabolite of Acrylonitrile (A191370) that forms phosphodiester adducts by reacting with nucelotides.

Technology Process of 2-Cyanoethylene oxide

There total 3 articles about 2-Cyanoethylene oxide 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: 60.0%

acrylonitrile (107-13-1,25014-41-9) → rac-oxiranecarbonitrile (4538-51-6)

Guidance literature:

With tert.-butylhydroperoxide; chromium silicalite-2; In methanol; at 65 ℃; for 5h;

DOI:10.1039/c39950001341

Reference yield:

2,3-epoxy-propionaldehyd-(O-acetyl oxime ) (116974-89-1) → rac-oxiranecarbonitrile (4538-51-6)

Guidance literature:

at 140 ℃; under 50 Torr;

DOI:10.1021/ja01527a035

Reference yield:

→ rac-oxiranecarbonitrile (4538-51-6)

Guidance literature:

Glycidaldehyd (O-acetyloxim); <140-145grad>;

upstream raw materials:

2,3-epoxy-propionaldehyd-(O-acetyl oxime )

acrylonitrile

Downstream raw materials:

N-acetyl-S-(2-cyano-2-hydroxyethyl)cysteine

N-acetyl-S-(1-cyano-2-hydroxyethyl)cysteine

glycolonitrile

sodium glyceraldehyde-2-phosphate

Refernces

• 1、 Kamata, Keigo,Sugahara, Kosei,Yonehara, Kazuhiro,Ishimoto, Ryo,Mizuno, Noritaka. "Efficient epoxidation of electron-deficient alkenes with hydrogen peroxide catalyzed by [γ-PW10O38V2(μ-OH) 2]3-". scheme or table. p. 7549 - 7559. Retrieved 2011/08/03.
• 2、 Pitsch, Stefan,Pombo-Villar, Esteban,Eschenmoser, Albert. "Chemistry of α-Aminonitriles. Formation of 2-Oxoethyl Phosphates ('Glycolaldehyde Phosphates') from rac-Oxiranecarbonitrile and on (Formal) Constitutional Relationships between 2-Oxoethyl Phosphates and Oligo(hexo- and pentopyranosyl)nucleotide Backbones". . p. 2251 - 2285. Retrieved 2007/10/02.