1515-99-7

Basic information

• Product Name: (-)-Methylphenylpropylphosphine oxide
• Synonyms: (-)-Methylphenylpropylphosphine oxide
• CAS NO: 1515-99-7
• Molecular Formula: C₁₀H₁₅OP
• Molecular Weight: 0
• Mol File: 1515-99-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-Methylphenylpropylphosphine oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Methylphenylpropylphosphine oxide(1515-99-7)
• EPA Substance Registry System: (-)-Methylphenylpropylphosphine oxide(1515-99-7)

Safety Data

• Hazardous Substances Data: 1515-99-7(Hazardous Substances Data)

Usage

General Description

(-)-Methylphenylpropylphosphine oxide is a chiral organophosphorus compound with the chemical formula C10H15OP. It is a white crystalline solid that is used as a resolving agent for the separation of chiral acids and bases, as well as in the synthesis of various pharmaceutical and agrochemical products. (-)-Methylphenylpropylphosphine oxide has two enantiomers, with the (-)-enantiomer being the more commonly encountered form. (-)-Methylphenylpropylphosphine oxide is known for its ability to selectively form complexes with specific chiral molecules, making it a valuable tool in the field of asymmetric synthesis and chiral resolution. Additionally, it is used as a ligand in transition metal-catalyzed asymmetric reactions to control the stereochemistry of the products.

Upstream product

• 80677-33-4 (R)-(+)-Methylphenyl-n-propyl-N-(p-toluolsulfonyl)phosphazen 
• 701-03-1 methylpropylphenylphosphine 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 7301-81-7 ethyl (S)-methyl(phenyl)phosphinate 
• 927-77-5 n-propylmagnesium bromide 
• 4653-63-8 methyl-phenyl-propyl-phosphine oxide 
• 114026-76-5 (-)-(2R,3R)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.5]decane 
• 2946-61-4 phenylphosphonous acid dimethyl ester 
• 644-97-3 Dichlorophenylphosphine 
• 6389-79-3 methyl methylphenylphosphinate 

Relevant articles and documents

Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery

Several dialkyl-arylphosphine oxides were prepared, and the enantioseparation of the corresponding racemates was elaborated with host–guest complexation using TADDOL-derivatives. The crystallization conditions were optimized and two separate crystallization methods, one in organic solvent, and the other in water, were found to yield five examples of phosphine oxides with enantiomeric excess values higher than 94 %. A gram scale resolution was performed, and both enantiomers of the methyl-phenyl-propyl-phosphine oxide were separated with (R,R)- or (S,S)-spiro-TADDOL. The intermolecular interactions responsible for the enantiomeric recognition between the chiral host and guest molecules were investigated by single-crystal X-ray diffractional structural determinations. The similarities in the structural patterns of a few diastereomeric crystals were checked by powder X-ray diffraction, as well. Organic solvent nanofiltration (OSN) was used as a scalable technique for the decomposition of the corresponding phosphine oxide–spiro-TADDOL molecular complexes, and for the recovery of the phosphine oxide enantiomers and resolving agents.

Stereoselective catalytic synthesis of P-stereogenic oxides via hydrogenative kinetic resolution

A highly stereoselective catalytic method for the preparation of structurally diverse P-stereogenic oxides has been developed. The approach relies on the ability of rhodium complexes derived from an enantiopure P-OP ligand to kinetically resolve racemic α,β-unsaturated phosphane oxides by hydrogenation of the C= C motif and formation of highly enantioenriched (or even enantiopure) P-stereogenic oxides. The practicality of the methodology has been demonstrated by the preparation of potentially functional P-chiral molecules for catalytic enantioselective synthesis.

OXIDATION REACTIONS BY MEANS OF ORGANIC SELENOXIDES

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