2,2-Diphenylcyclopropanecarbonitrile

Base Information

• Chemical Name: 2,2-Diphenylcyclopropanecarbonitrile
• CAS No.: 30932-41-3
• Molecular Formula: C₁₆H₁₃N
• Molecular Weight: 219.286
• Hs Code.: 29269090
• European Community (EC) Number: 250-397-1
• NSC Number: 120433
• DSSTox Substance ID: DTXSID801292080
• Nikkaji Number: J287.413J
• Mol file: 30932-41-3.mol

Synonyms:2,2-Diphenylcyclopropanecarbonitrile;30932-41-3;2,2-diphenylcyclopropane-1-carbonitrile;Cyclopropanecarbonitrile, 2,2-diphenyl-;EINECS 250-397-1;2,2-Diphenylcyclopropane carbonitrile;NSC120433;SCHEMBL9543115;DTXSID801292080;AMY40699;MFCD00182382;TD8144;AKOS015998965;CS-W013152;NSC 120433;NSC-120433;DS-18486;FT-0689998;A853851

Chemical Property of 2,2-Diphenylcyclopropanecarbonitrile

Chemical Property:

• Vapor Pressure: 8.11E-06mmHg at 25°C
• Melting Point: 108-110℃
• Refractive Index: 1.624
• Boiling Point: 374.9 °C at 760 mmHg
• Flash Point: 141.3 °C
• PSA: 23.79000
• Density: 1.14 g/cm³
• LogP: 3.51618
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 219.104799419
• Heavy Atom Count: 17
• Complexity: 294

Purity/Quality:

99.9% ^*data from raw suppliers

2,2-Diphenylcyclopropanecarbonitrile ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C1(C2=CC=CC=C2)C3=CC=CC=C3)C#N
• Uses: 2,2-Diphenylcyclopropanecarbonitrile is used in the synthetic preparation of cyclopropanation or metathesis products by reactions of diazo compds. with alkenes catalyzed by [RuCl(cod)(Cp)].

Technology Process of 2,2-Diphenylcyclopropanecarbonitrile

There total 25 articles about 2,2-Diphenylcyclopropanecarbonitrile 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: 73.6%

benzophenone hydrazone (5350-57-2) + acrylonitrile (107-13-1,25014-41-9) → 1-cyano-2,2-diphenylcyclopropane (28098-84-2,51154-93-9,151436-92-9,30932-41-3)

Guidance literature:

benzophenone hydrazone; With tetrabutylammomium bromide; dihydrogen peroxide; In Petroleum ether; at 25 ℃; for 3h;

acrylonitrile; In diethyl ether; for 0.5h; Temperature; Reagent/catalyst; Reflux;

Reference yield: 71.0%

3,3-diphenylcyclobutan-1-one O-(4-(trifluoromethyl)benzoyl)oxime → 1-cyano-2,2-diphenylcyclopropane (28098-84-2,51154-93-9,151436-92-9,30932-41-3)

Guidance literature:

3,3-diphenylcyclobutan-1-one O-(4-(trifluoromethyl)benzoyl)oxime; With (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Glovebox;

With lithium hexamethyldisilazane; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1055/s-0039-1690872

Reference yield: 55.0%

3,3-diphenylacrylonitrile (3531-24-6) + trimethylsulfoxonium iodide (1774-47-6) → 1-cyano-2,2-diphenylcyclopropane (28098-84-2,51154-93-9,151436-92-9,30932-41-3)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; at 0 - 20 ℃;

DOI:10.1080/00397910802006388

upstream raw materials:

acrylonitrile

diazodiphenylmethane

benzaldehyde p-toluenesulfonylhydrazone

Dichlorodiphenylmethane

Downstream raw materials:

2,2-diphenylcyclopropyl 2-pyridyl ketimine

3,3-diphenylpropionitrile

5-Diethylamino-4,4-diphenyl-hexanenitrile

1-Aminomethyl-2,2-diphenyl cyclopropane hydrochloride

Refernces

• 1、 Hock, Katharina J.,Spitzner, Robin,Koenigs, Rene M.. "Towards nitrile-substituted cyclopropanes-a slow-release protocol for safe and scalable applications of diazo acetonitrile". supporting information. p. 2118 - 2122. Retrieved 2017/07/24.
• 2、 Saitoh, Hideki,Watanabe, Tatsuya,Kimura, Tsutomu,Kato, Yuichi,Satoh, Tsuyoshi. "New synthesis of multisubstituted cyanocyclopropanes by the intramolecular SN2 alkylation and 1,3-CC insertion reaction of magnesium carbenoids as the key reactions". scheme or table. p. 2481 - 2495. Retrieved 2012/05/05.