24901-29-9

Basic information

• Product Name: 3-methyl-1-phenylphospholane
• CAS NO: 24901-29-9
• Molecular Formula: C₁₁H₁₅P
• Molecular Weight: 178.2106
• Mol File: 24901-29-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 264.3°C at 760 mmHg
• Flash Point: 117.5°C
• Vapor Pressure: 0.016mmHg at 25°C
• CAS DataBase Reference: 3-methyl-1-phenylphospholane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-1-phenylphospholane(24901-29-9)
• EPA Substance Registry System: 3-methyl-1-phenylphospholane(24901-29-9)

Safety Data

• Hazardous Substances Data: 24901-29-9(Hazardous Substances Data)

Upstream product

• 34868-22-9 3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-phosphole-1-oxide 
• 7564-51-4 2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide 
• 29587-76-6 (+)-3r-methyl-1-phenyl-phospholane 1t-oxide 

Downstream Products

• 538-75-0 dicyclohexyl-carbodiimide 
• 34868-24-1 1-iodomethyl-3-methyl-1-phenyl-phospholanium; iodide 
• 1192586-20-1 1-(2-methoxy-2-oxoethyl)-3-methyl-1-phenylphospholanium bromide 
• 313478-78-3 3-methyl-1-phenylphospholane-borane complex 
• 19713-73-6 methyl (2Z)-3-phenylprop-2-enoate 
• 103-26-4 Methyl cinnamate 

Relevant articles and documents

Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination

A novel bridged [2.2.1] bicyclic phosphine oxide, devised to circumvent the waste generation and burdens of purification that are typical of reactions driven by the generation of phosphine oxides, has been prepared in three steps from commercially availab

Part I: The development of the catalytic wittig reaction

We have developed the first catalytic (in phosphane) Wittig reaction (CWR). The utilization of an organosilane was pivotal for success as it allowed for the chemoselective reduction of a phosphane oxide. Protocol optimization evaluated the phosphane oxide precatalyst structure, loading, organosilane, temperature, solvent, and base. These studies demonstrated that to maintain viable catalytic performance it was necessary to employ cyclic phosphane oxide precatalysts of type 1. Initial substrate studies utilized sodium carbonate as a base, and further experimentation identified N,N-diisopropylethylamine (DIPEA) as a soluble alternative. The use of DIPEA improved the ease of use, broadened the substrate scope, and decreased the precatalyst loading. The optimized protocols were compatible with alkyl, aryl, and heterocyclic (furyl, indolyl, pyridyl, pyrrolyl, and thienyl) aldehydes to produce both di- and trisubstituted olefins in moderate-to-high yields (60-96 %) by using a precatalyst loading of 4-10 mol %. Kinetic E/Z selectivity was generally 66:34; complete E selectivity for disubstituted α,β-unsaturated products was achieved through a phosphane-mediated isomerization event. The CWR was applied to the synthesis of 54, a known precursor to the anti-Alzheimer drug donepezil hydrochloride, on a multigram scale (12.2 g, 74 % yield). In addition, to our knowledge, the described CWR is the only transition-/heavy-metal-free catalytic olefination process, excluding proton-catalyzed elimination reactions. A point of difference: By utilizing an organosilane to chemoselectively reduce a phosphane oxide precatalyst to a phosphane (see scheme), the first catalytic (in phosphane) Wittig reaction has been developed. The methodology has been applied to the synthesis of 22 disubstituted and 24 trisubstituted olefins, including a multigram synthesis of a precursor to the anti-Alzheimer drug donepezil hydrochloride.

A new family of platinum(ii) complexes incorporating five-and six-membered cyclic phosphine ligands

New platinum complexes of the type cis-Pt(L)2Cl2 have been synthesized from five-and six-membered cyclic phosphines, which were prepared after deoxygenating a series of phosphine oxides (3-phospholene oxides, phospholane oxides, a 1,