3282-18-6

Basic information

• Product Name: 1,1-Diphenylcyclopropane
• Synonyms: 1,1-Diphenylcyclopropane
• CAS NO: 3282-18-6
• Molecular Formula: C₁₅H₁₄
• Molecular Weight: 194.27166
• Mol File: 3282-18-6.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 140 °C
• Appearance: /
• Density: 1.0330 g/cm3
• CAS DataBase Reference: 1,1-Diphenylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Diphenylcyclopropane(3282-18-6)
• EPA Substance Registry System: 1,1-Diphenylcyclopropane(3282-18-6)

Safety Data

• Hazardous Substances Data: 3282-18-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 2467, 1989 DOI: 10.1021/jo00271a048

Upstream product

• 186581-53-3 diazomethane 
• 530-48-3 1,1-Diphenylethylene 
• 60-29-7 diethyl ether 
• 25201-66-5 5,5-diphenyl-4,5-dihydro-1H-pyrazole 
• 75-77-4 chloro-trimethyl-silane 
• 17343-74-7 1,1-dibromo-2,2-diphenylcyclopropane 
• 50462-56-1 1-diazo-2,2-diphenylpropane 
• 3141-42-2 2,2-diphenyl-1,1-dichlorocyclopropane 
• 74-85-1 ethene 
• 908093-98-1 diazodiphenylmethane 
• 132776-00-2 (+)-(S)-1-fluoro-1-iodo-2,2-diphenylcyclopropane 
• 19255-91-5 (2-chlorocyclopropane-1,1-diyl)dibenzene 
• 5909-90-0 N-(2,2-diphenylcyclopropyl)-N-nitrosourea 
• 14399-53-2 bis(iodomethyl)zinc 

Downstream Products

• 120062-19-3 1-Chloro-1-diisopropylamino-2,2-diphenyl-phosphetanium 
• 778-66-5 1,1-diphenyl-1-propene 
• 26461-03-0 1-phenylindane 
• 1530-03-6 1,1-diphenylpropane 
• 42558-10-1 1,1-bis-(4-nitrophenyl)cyclopropane 
• 38899-54-6 2-methyl-5,5-diphenyl-2-pentanol 

Relevant articles and documents

Oxidative addition of a strained C-C bond onto electron-rich rhodium(I) at room temperature

The C-C bond of cyclobutanones undergoes oxidative addition to a T-shape rhodium(I) complex possessing a PBP pincer ligand at room temperature. The remarkable propensity of the rhodium complex for oxidative addition is attributed to the highly electron-donating nature of the boron ligand as well as the unsaturation on the rhodium center.

Intermolecular Electrophilic Bromoesterification and Bromoetherification of Unactivated Cyclopropanes

1,3-difunctionalization of cyclopropane is an useful organic transformation. The corresponding 1,3-difunctionalized products are synthetic synthons and building blocks in many organic syntheses. Many existing ring-opening difunctionalization methodologies rely primarily on the use of donor?acceptor cyclopropanes, while the difunctionalization of unactivated cyclopropanes is less exploited. In this research, 1,3-bromoesterification and 1,3-bromoetherification of unactivated cyclopropanes were successfully achieved using N-bromosuccinimide as the brominating agent with high yields and regioselectivity. (Figure presented.).

Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes

A highly stereocontrolled syn-addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper-catalyzed C?Si bond formation closes the gap of the direct synthesis of α-chiral cyclopropylsilanes.

A Modular Approach to the Synthesis of gem-Disubstituted Cyclopropanes

A diastereoselective, Pd-catalyzed Suzuki-Miyaura coupling reaction of geminal bis(boryl)cyclopropanes has been developed. The reaction offers a highly modular approach to the synthesis of tertiary cyclopropylboronic esters. The resulting boronic esters may be further functionalized to afford a range of gem-disubstituted cyclopropanes, which represent an important structural motif in the pharmaceutical industry. Sequential Suzuki-Miyaura cross-coupling reactions of gem-bis(boryl)cyclopropanes are also reported. The coupling protocols are compatible with a broad range of functionalized aryl and heteroaryl bromides.