phenyl(2-phenylcyclopropyl)methanone

Base Information

• Chemical Name: phenyl(2-phenylcyclopropyl)methanone
• CAS No.: 1145-91-1
• Molecular Formula: C16H14 O
• Molecular Weight: 222.287
• Mol file: 1145-91-1.mol

Synonyms:Ketone,phenyl 2-phenylcyclopropyl, cis- (8CI); Methanone,phenyl(2-phenylcyclopropyl)-, cis-; NSC 172578; cis-1-Benzoyl-2-phenylcyclopropane

Chemical Property of phenyl(2-phenylcyclopropyl)methanone

Chemical Property:

• Vapor Pressure: 2.73E-05mmHg at 25°C
• Boiling Point: 357.4°C at 760 mmHg
• Flash Point: 155.1°C
• Density: 1.143g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of phenyl(2-phenylcyclopropyl)methanone

There total 22 articles about phenyl(2-phenylcyclopropyl)methanone 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: 83.0%

E-1-bromo-1-benzoyl-2-phenylcyclopropane (108401-93-0,112252-76-3,113446-15-4) → cis-(2-phenylcyclopropyl)(phenyl)methanone (1145-91-1)

Guidance literature:

With sodium isopropylate; In diethyl ether; for 2h; Heating;

Reference yield: 72.0%

cis-1-bromo-2-phenylcyclopropane (32523-76-5) + benzoyl chloride (98-88-4) → cis-(2-phenylcyclopropyl)(phenyl)methanone (1145-91-1)

Guidance literature:

cis-1-bromo-2-phenylcyclopropane; With TurboGrignard; In tetrahydrofuran; 1,4-dioxane; at 25 ℃; for 8h; Inert atmosphere;

benzoyl chloride; With copper(I) cyanide*2 lithium chloride; In tetrahydrofuran; 1,4-dioxane; at 0 - 25 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0028-1087487

Reference yield: 70.5%

phenyl[(1S,2S)-2-phenylcyclopropyl]methanone (21019-54-5) → (1SR,2SR)-phenyl(2-phenylcyclopropyl)ketone (1145-92-2) + cis-(2-phenylcyclopropyl)(phenyl)methanone (1145-91-1)

Guidance literature:

With di-tert-butyl diperoxyoxalate; 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole; In acetonitrile; at 22 ℃; for 22h; Product distribution; Mechanism; other radical initiator (AIBN), var. temp. and times; relative rate constants for cyclization of the radical intermediate;

DOI:10.1021/ja00028a045

upstream raw materials:

benzoic acid methyl ester

1,1-dibromo-2-phenylcyclopropane

phenyl[(1S,2S)-2-phenylcyclopropyl]methanone

(1SR,2SR)-phenyl(2-phenylcyclopropyl)ketone

Refernces

• 1、 Paternoga, Jan,Kühlborn, Jonas,Rossdam, Nils Ole,Opatz, Till. "Hantzsch Ester-Mediated Photochemical Transformations in the Ketone Series: Remote C(sp3)-H Arylation and Cyclopentene Synthesis through Strain Release". supporting information. p. 3232 - 3248. Retrieved 2021/02/27.
• 2、 Rauhut, Christian B.,Cervino, Christian,Krasovskiy, Arkady,Knochel, Paul. "Stereoselective preparation of cyclopropylmagnesium reagents via a Br-Mg exchange using i-PrMgCl·LiCl in the presence of dioxane". experimental part. p. 67 - 70. Retrieved 2009/05/28.