3-Oxocyclobutanecarbonitrile

Base Information

• Chemical Name: 3-Oxocyclobutanecarbonitrile
• CAS No.: 20249-16-5
• Molecular Formula: C5H5NO
• Molecular Weight: 95.1008
• Hs Code.: 2926909090
• European Community (EC) Number: 867-362-7
• DSSTox Substance ID: DTXSID10517634
• Nikkaji Number: J1.486.404K
• Wikidata: Q72498596
• Mol file: 20249-16-5.mol

Synonyms:3-Oxocyclobutanecarbonitrile;20249-16-5;3-oxocyclobutane-1-carbonitrile;3-OXO-CYCLOBUTANECARBONITRILE;Cyclobutanecarbonitrile, 3-oxo-;MFCD01087798;LCZC2533;DTXSID10517634;MSAGLWTVMUDVDT-UHFFFAOYSA-N;AKOS006272020;CS-W004195;GS-3710;PB12223;SY024404;AM20070603;FT-0648472;EN300-179155;A879758;J-013150

Chemical Property of 3-Oxocyclobutanecarbonitrile

Chemical Property:

• Vapor Pressure: 0.023mmHg at 25°C
• Boiling Point: 249℃
• Flash Point: 105℃
• PSA: 40.86000
• Density: 1.13
• LogP: 0.48908
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 95.037113783
• Heavy Atom Count: 7
• Complexity: 133

Purity/Quality:

98% ^*data from raw suppliers

3-Oxocyclobutanecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(CC1=O)C#N

Technology Process of 3-Oxocyclobutanecarbonitrile

There total 5 articles about 3-Oxocyclobutanecarbonitrile 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: 100.0%

3-methylenecyclobutanecarbonitrile (15760-35-7) → 3-oxo-cyclobutanecarbonitrile (20249-16-5)

Guidance literature:

With sodium periodate; ruthenium(III) trichloride hydrate; In dichloromethane; water; acetonitrile; at 5 - 20 ℃;

Reference yield: 80.0%

3-oxo-2-trimethylsilyl-cyclobutane-carbonitrile (339529-30-5) → 3-oxo-cyclobutanecarbonitrile (20249-16-5)

Guidance literature:

With ammonium fluoride; In methanol; at 10 ℃; for 3h;

DOI:10.1016/S0040-4020(01)00055-2

Reference yield:

5-nitro-2-pentanone (22020-87-7) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) → 3-oxo-cyclobutanecarbonitrile (20249-16-5) + (Z)-4-oxo-pent-2-enenitrile

Guidance literature:

5-nitro-2-pentanone; trimethylsilyl trifluoromethanesulfonate; With triethylamine; In dichloromethane; at 20 ℃; for 50h;

With ammonium fluoride; In methanol; at 10 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(01)00055-2

upstream raw materials:

3-methylenecyclobutanecarbonitrile

5-nitro-2-pentanone

trimethylsilyl trifluoromethanesulfonate

3-oxo-2-trimethylsilyl-cyclobutane-carbonitrile

Downstream raw materials:

3-(cyanomethylene)cyclobutane-1-carbonitrile

(3,3-difluorocyclobutyl)methanol

ethyl 3,3-difluorocyclobutane-1-carboxylate

3,3-difluorocyclobutane-1-carbaldehyde

Refernces

• 1、 -. "2 Tyrosine kinase mediated signal transduction inhibitors". Paragraph 0513; 0514; 0515. . Retrieved 2019/09/17.
• 2、 -. "IMIDAZO[1,2-A]PYRIDINES AS SOLUBLE GUANYLATE CYCLASE STIMULATORS FOR THE TREATMENT OF CARDIOVASCULAR DISEASES". Paragraph 1061; 1062; 1063; 1064. . Retrieved 2017/03/21.