14633-95-5

Basic information

• Product Name: CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE
• Synonyms: CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE
• CAS NO: 14633-95-5
• Molecular Formula: C₂₁H₁₉P
• Molecular Weight: 302.349321
• Mol File: 14633-95-5.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 465.7±28.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• CAS DataBase Reference: CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE(14633-95-5)
• EPA Substance Registry System: CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE(14633-95-5)

Safety Data

• Hazardous Substances Data: 14633-95-5(Hazardous Substances Data)

Usage

Description

CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE is a phosphorane derivative with the molecular formula C21H19P, featuring a cyclopropylidene group and three phenyl rings attached to a phosphorus atom. It is a high reactivity and stability chemical compound, commonly used as a reagent in organic synthesis.

Uses

Used in Organic Synthesis:
CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE is used as a reagent for the Wittig reaction, a method for the formation of carbon-carbon double bonds. It is utilized for the creation of complex organic molecules.
Used in Pharmaceutical Industry:
CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE is used as an important intermediate in the pharmaceutical field, aiding in the synthesis of various pharmaceutical compounds.
Used in Agrochemical Industry:
In the agrochemical industry, CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE is used as a key intermediate for the synthesis of agrochemical products.
Used in Materials Science:
CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE is also used in materials science, contributing to the development of new materials through its role in organic synthesis.

Upstream product

• 603-35-0 triphenylphosphine 
• 109-64-8 1,3-dibromo-propane 
• 873332-53-7 6-(4-nitro-phenyl)-4,4,4-triphenyl-5-oxa-4λ⁵-phospha-spiro[2.3]hexane-6-carboxylic acid methyl ester 
• 76757-83-0 Cyclopropyltriphenylphosphonium-tetrafluoroborat 
• 14114-05-7 cyclopropyltriphenylphosphonium bromide 
• 3607-17-8 3-bromopropyltriphenylphosphonium bromide 

Downstream Products

• 7632-57-7 diphenylmethylenecyclopropene 
• 23154-08-7 (Methylcyclopropylmethylene)cyclopropane 
• 76757-63-6 C₂₂H₂₂PS⁽¹⁺⁾*BF₄^(1-) 
• 76757-67-0 C₂₃H₂₆PS₂⁽¹⁺⁾*BF₄^(1-) 
• 76757-65-8 C₂₄H₂₆PS⁽¹⁺⁾*BF₄^(1-) 
• 73673-90-2 1-(cyclopropylidenemethyl)-4-nitrobenzene 
• 7555-67-1 1-phenylmethylenecyclopropane 
• 155397-53-8 1-(2-Cyclopropylidene-propylsulfanyl)-4-methyl-benzene 
• 162377-97-1 5-(cyclopropylidene)pentan-1-ol 
• 1125406-88-3 C₁₈H₁₇BrO₂ 

Relevant articles and documents

Activation and Functionalization of C-C σ Bonds of Alkylidene Cyclopropanes at Main Group Centers

Aluminum(I) and magnesium(I) compounds are reported for the C-C σ-bond activation of strained alkylidene cyclopropanes. These reactions result in the formal addition of the C-C σ bond to the main group center either at a single site (Al) or across a metal-metal bond (Mg-Mg). Mechanistic studies suggest that rather than occurring by a concerted oxidative addition, these reactions involve stepwise processes in which substrate binding to the main group metal acts as a precursor to α- or β-alkyl migration steps that break the C-C σ bond. This mechanistic understanding is used to develop the magnesium-catalyzed hydrosilylation of the C-C σ bonds of alkylidene cyclopropanes.

Organoselenium-Catalyzed Oxidative Ring Expansion of Methylenecyclopropanes with Hydrogen Peroxide

Catalyst screening and optimization of reaction conditions allowed control of the organoselenium-catalyzed oxidative ring expansion of highly active methylenecyclopropanes to give substituted cyclobutanones selectively. This protocol employs H2O2 as a clean oxidant and generates no waste and, therefore, provides green access to useful, but not readily available, substituted cyclobutanones under mild conditions.

First isolation and characterization of 1,2-oxaphosphetanes with three phenyl groups at the phosphorus atom in typical Wittig reaction using cyclopropylidenetriphenylphosphorane

1,2-Oxaphosphetanes bearing three phenyl groups directly bound to the phosphorus atom were successfully isolated for the first time as stable crystals in the typical Wittig reaction of cyclopropylidenetriphenylphosphorane with activated carbonyl compounds. X-ray analysis of the oxaphosphetane showed that the phosphorus atom is at the center of a slightly distorted trigonal bipyramidal structure. Thermal decomposition of these oxaphosphetanes was carried out to give the starting carbonyl compounds and Wittig reaction products, olefins.