7150-12-1

Basic information

• Product Name: 2,2-DIPHENYL-CYCLOPROPANECARBOXYLIC ACID
• Synonyms: 2,2-DIPHENYL-CYCLOPROPANECARBOXYLIC ACID;AKOS AU36-M81;Einecs 230-484-0;2,2-diphenylcyclopropane-1-carboxylic acid
• CAS NO: 7150-12-1
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.28
• EINECS: 230-484-0
• Mol File: 7150-12-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 166-169 °C
• Boiling Point: 403 °C at 760 mmHg
• Flash Point: 185.8 °C
• Appearance: /
• Density: 1.239 g/cm³
• Vapor Pressure: 3.23E-07mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.40±0.11(Predicted)
• CAS DataBase Reference: 2,2-DIPHENYL-CYCLOPROPANECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIPHENYL-CYCLOPROPANECARBOXYLIC ACID(7150-12-1)
• EPA Substance Registry System: 2,2-DIPHENYL-CYCLOPROPANECARBOXYLIC ACID(7150-12-1)

Safety Data

• Hazardous Substances Data: 7150-12-1(Hazardous Substances Data)

Usage

Uses

2,2-Diphenylcyclopropanecarboxylic Acid is an intermediate in the synthesis of Cibenzoline, an antiarrhythmic drug that relieves the outflow tract obstruction of hypertrophic obstructive cardiomyopathy (HOCM).

InChI:InChI=1/C16H14O2/c17-15(18)14-11-16(14,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11H2,(H,17,18)

Upstream product

• 201230-82-2 carbon monoxide 
• 17343-74-7 1,1-dibromo-2,2-diphenylcyclopropane 
• 19481-83-5 1-bromo-2,2-diphenylcyclopropanecarboxylic acid 
• 292638-85-8 acrylic acid methyl ester 
• 908093-98-1 diazodiphenylmethane 
• 67428-04-0 ethyl 2,2-diphenylcyclopropane-1-carboxylate 
• 1033827-76-7 methyl (E)-3-(2,2-diphenylcyclopropyl)prop-2-enoate 
• 1033827-77-8 (Z)-3-(2,2-diphenylcyclopropyl)prop-2-enenitrile 
• 1033827-75-6 2-(2-methoxyethenyl)-1,1-diphenylcyclopropane 
• 1033827-74-5 1-[(E)-2-phenylethenyl]-2,2-diphenylcyclopropane 
• 124-38-9 carbon dioxide 
• 22825-21-4 3,3-diphenylcyclopropene 
• 32812-52-5 1-bromo-2,2-diphenyl cyclopropane 
• 5350-57-2 benzophenone hydrazone 

Downstream Products

• 53692-74-3 (R)-2,2-diphenylcyclopropanecarboxylic acid 
• 53692-73-2 (1S)-2,2-diphenylcyclopropane carboxylic acid 
• 88082-48-8 2,2-Diphenyl-1-trimethylsilanyl-cyclopropanecarboxylic acid 
• 37555-47-8 2-Amino-1,1-diphenyl-cyclopropan 
• 1333015-64-7 1-[(Z)-2-phenylethenyl]-2,2-diphenylcyclopropane 
• 1333015-65-8 1-[(Z)-2-p-tolylethenyl]-2,2-diphenylcyclopropane 
• 1333015-80-7 1-[(E)-2-p-tolylethenyl]-2,2-diphenylcyclopropane 
• 1333015-66-9 1-[(Z)-2-(3-chlorophenyl)ethenyl]-2,2-diphenylcyclopropane 
• 1333015-81-8 1-[(E)-2-(3-chlorophenyl)ethenyl]-2,2-diphenylcyclopropane 
• 1333015-67-0 1-[(Z)-2-(4-methoxyphenyl)ethenyl]-2,2-diphenylcyclopropane 
• 1333015-82-9 1-[(E)-2-(4-methoxyphenyl)ethenyl]-2,2-diphenylcyclopropane 
• 1333015-68-1 1-[(Z)-2-(4-nitrophenyl)ethenyl]-2,2-diphenylcyclopropane 
• 1333015-83-0 1-[(E)-2-(4-nitrophenyl)ethenyl]-2,2-diphenylcyclopropane 
• 1333015-69-2 2,2-diphenyl-1-{(Z)-2-[(E)-4-styrylphenyl]ethenyl}cyclopropane 

Relevant articles and documents

Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide

A nickel-catalyzed reductive carboxylation technique for the synthesis of cyclopropanecarboxylic acids has been developed. This user-friendly and mild transformation operates at atmospheric pressure of carbon dioxide and utilizes either organic halides or alkene precursors, thus representing the first example of catalytic reductive carboxylation of secondary counterparts lacking adjacent π-components.

The cyclopropyl group as a hypersensitive probe in the singlet oxygen ene reaction mechanism

(Chemical Equation Presented) Cyclopropyl-substituted olefins are employed as mechanistic probes in the singlet oxygen-alkene ene reaction. In MeOH and aprotic solvents [CHCl3, (CH3)2CO, CH 3CN], only the allylic hydroperoxides bearing an intact cyclopropyl group are detected. The reaction mechanism is independent of solvent polarity. Our findings, to a certain experimental limit, exclude a biradical or dipolar intermediate.

Diazodiphenylmethane and monosubstituted butadienes: Kinetics and a new chapter of vinylcyclopropane chemistry

Diazodiphenylmethane (DDM) undergoes cycloadditions to 1-substituted buta-1,3-dienes exclusively at the C(3)=C(4) bond. At room temperature, the N2 loss from the initially formed 4,5-dihydro-3H-pyrazoles 2 is faster than the cycloaddition and furnishes the vinylcyclopropane derivatives 7 and 9 with structural retention at the C(1)=C(2) bond. 2-Substituted butadienes react with DDM at the C(3)=C(4) bond to give 12; isoprene, however, affords 3,4/1,2 products in the ratio of 86:14. DDM is a nucleophilic 1,3-dipole: 1-Cyanobutadiene reacts 400 times faster than 1-methoxybuta-1,3-diene (DMF, 40°). The log k2 for the additions to six 1-substituted butadienes show a linear correlation with σp (Hammett) and ρ = +2.9; the log k2 of five 2-substituted butadienes are linearly related to Taft's σI (ρ = +1.7). The structures of the vinylcyclopropanes 7, 9, and 12 are established by NMR spectra and oxidation. A cyclopropyl carbinyl cation is made responsible for the isomerization of 12, R = Ph, Me, by acetic acid to 4-substituted 1,1-diphenylpenta-1,3-dienes 25 and 29; TsOH at 200° converts 25 further to 9,10-dihydro-9-methyl-10-phenyl-9,10-ethanoanthracene (27). Thermal rearrangement of 7, 9, and 12 at 200-300° produces the 3- or 1-substituted 4,4-diphenylcyclopentenes 30 and 31. These give the same mass spectra as the vinylcyclopropanes, and an open-chain distonic radical cation is suggested as common intermediate. Besides spectroscopic evidence for the cyclopentene structures, hydrogenation and epoxidation are described; NMR data support the trans-attack by perbenzoic acid.