Cyclobutylideneacetonitrile

Base Information

• Chemical Name: Cyclobutylideneacetonitrile
• CAS No.: 27784-69-6
• Molecular Formula: C6H7N
• Molecular Weight: 93.1283
• Hs Code.: 2926909090
• European Community (EC) Number: 817-996-5
• DSSTox Substance ID: DTXSID20543020
• Mol file: 27784-69-6.mol

Synonyms:Cyclobutylideneacetonitrile;2-Cyclobutylideneacetonitrile;27784-69-6;Cyclobutylidene-acetonitrile;cyanomethylenecyclobutane;DTXSID20543020;BRZXIZFUVMXDAQ-UHFFFAOYSA-N;MFCD12963766;AKOS017515305;SB12938;CS-0183324;EN300-216219;P11568;A1-01107

Chemical Property of Cyclobutylideneacetonitrile

Chemical Property:

• PSA: 23.79000
• LogP: 1.62028
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 93.057849228
• Heavy Atom Count: 7
• Complexity: 130

Purity/Quality:

98.5% ^*data from raw suppliers

Cyclobutylideneacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=CC#N)C1

Technology Process of Cyclobutylideneacetonitrile

There total 2 articles about Cyclobutylideneacetonitrile 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: 90.3%

cyclobutanone (1191-95-3) + cyanomethylene triphenylphosphorane (16640-68-9) → 2-cyclobutylideneacetonitrile (27784-69-6)

Guidance literature:

In dichloromethane; at 20 ℃; for 3h;

Reference yield: 57.0%

cyclobutanone (1191-95-3) + diethyl 1-cyanomethylphosphonate (2537-48-6) → 2-cyclobutylideneacetonitrile (27784-69-6)

Guidance literature:

diethyl 1-cyanomethylphosphonate; With triethylamine; lithium bromide; In tetrahydrofuran; at 25 ℃; for 2h; Inert atmosphere;

cyclobutanone; In tetrahydrofuran; at 25 ℃; for 16h;

Reference yield: 74.0%

2-cyclobutylideneacetonitrile (27784-69-6) + N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) → 6-benzyl-6-azaspiro[3.4]octane-8-carbonitrile

Guidance literature:

In acetonitrile; at 60 ℃;

DOI:10.1002/ejoc.201700536

upstream raw materials:

cyclobutanone

diethyl 1-cyanomethylphosphonate

cyanomethylene triphenylphosphorane

Refernces

• 1、 Zhou, Bingnan,Wu, Qiuyue,Dong, Ziyang,Xu, Jiaxi,Yang, Zhanhui. "Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization". supporting information. p. 3594 - 3599. Retrieved 2019/05/24.
• 2、 Chalyk, Bohdan A.,Isakov, Andrei A.,Butko, Maryna V.,Hrebeniuk, Kateryna V.,Savych, Olena V.,Kucher, Olexandr V.,Gavrilenko, Konstantin S.,Druzhenko, Tetiana V.,Yarmolchuk, Vladimir S.,Zozulya, Sergey,Mykhailiuk, Pavel K.. "Synthesis of 6-Azaspiro[4.3]alkanes: Innovative Scaffolds for Drug Discovery". . p. 4530 - 4542. Retrieved 2017/08/30.