1515-99-7

Usage

Uses

Used in Pharmaceutical Industry:
(-)-Methylphenylpropylphosphine oxide is used as a resolving agent for the separation of chiral acids and bases, which is crucial in the synthesis of various pharmaceutical products. Its ability to selectively form complexes with specific chiral molecules aids in obtaining the desired enantiomers, which can have different biological activities and properties.
Used in Agrochemical Industry:
(-)-Methylphenylpropylphosphine oxide is also used in the synthesis of various agrochemical products, where the separation and resolution of chiral compounds are essential for the development of effective and targeted pesticides or herbicides.
Used in Asymmetric Synthesis:
(-)-Methylphenylpropylphosphine oxide is used as a ligand in transition metal-catalyzed asymmetric reactions to control the stereochemistry of the products. This application is vital for the production of enantiomerically pure compounds, which are often required for biological activity and to avoid potential side effects.
Used in Chiral Resolution:
(-)-Methylphenylpropylphosphine oxide is used as a resolving agent in chiral resolution processes, where it helps in separating enantiomers that have different configurations but the same molecular formula. This is important for obtaining pure enantiomers for various applications, including pharmaceuticals and agrochemicals.

Upstream product

• 917-64-6 methyl magnesium iodide 
• 87219-88-3 (R)-Phenyl-propyl-phosphinic acid (S)-3-bromo-1-methyl-propyl ester 
• 13153-91-8 (-)-(S)-methyl-n-propylphenylphosphine sulphide 
• 3400-27-9 2-methyl-3-p-nitrophenyloxaziridine 
• 701-03-1 methylpropylphenylphosphine 
• 13153-92-9 (+)-(R)-methyl-n-propylphenylphosphine sulphide 
• 34641-79-7 (+)R-methyl-n-propylphenylphosphine selenide 
• 701-03-1 (+)-(S)-methyl-n-propyl phenylphosphine 
• 927-77-5 n-propylmagnesium bromide 
• 18944-66-6 (R)-isopropoxy(methyl)phenylphosphine oxide 
• 676-58-4 methylmagnesium chloride 
• 701-03-1 (-)-(R)-methyl-n-propylphenylphosphine 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 7301-81-7 ethyl (S)-methyl(phenyl)phosphinate 

Relevant academic research and scientific papers

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.

A facile and practical preparation ofP-chiral phosphine oxides

A practical and cost-effective synthetic method ofP-chiral diarylalkyl, aryldialkyl, and triaryl phosphine oxides by using readily available chiral diphenyl-2-pyrrolidinemethanol as the auxiliary is developed. The long-standing racemization issue during s

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.

SILYLPEROXIDES AS SELECTIVE OXYGENATION REAGENTS IN PHOSPHORUS CHEMISRTY

Bis(trimethylsilyl)peroxide (BSPO) can be used for chemo- and stereoselective generation of P=O group by oxygenation of P(III) centre and transformation of P=S and P=Se groups.

Optically Active Phosphine Oxides. 2. Novel Approach to Enantiomeric Dialkylphenylphosphine Oxides

New routes to optically active tertiary phosphine oxides of known configuration and of virtually 100percent enantiomeric purity have been developed.Alkylation of (-)-(SP)-ethyl((menthoxycarbonyl)methyl)phenylphosphine oxide (2) by treatment wit

The Mechanisms of the Conversion of Thiophosphoryl Compounds into their Phosphoryl Analogues by Photochemically Excited 3-Methylpyridazine 2-Oxide and by 2-Methyl-3-p-nitrophenyloxaziridine; a Comparison

Reactions of tri-p-substituted triarylphosphine sulphides with 3-methylpyridazine 2-oxide, under photolysis, and with 2-methyl-3-p-nitrophenyloxaziridine both give the corresponding phosphine oxides.A detailed study and comparison of the two reactions shows that they are mechanistically quite distinct and that it is unlikely that the active oxygenating species generated by photolysis of the N-oxide, which attacks the phosphine sulphides, is an oxaziridine.The evidence presented suggests that this species may in fact be 'oxene'.

PREPARATION OF OPTICALLY ACTIVE PHOSPHINE OXIDES BY REGIOSELECTIVE CLEAVAGE OF CYCLIC PHENYLPHOSPHONITE WITH ALKYL HALIDES

The Arbuzov reaction of (2S,4S)-methyl-2-phenyl-1,3,2-dioxaphosphorinane with various alkyl halides gave the diastereomerically pure phosphinates with regioselective cleavage of the primary carbon-oxygen bond.These phosphinates reacted with Grignard reage

Mechanisms in Electrophilic Reactions of Reactive Nitrogen Compounds with Phosphanes

Chiral phosphanes were used as nucleophiles in reactions with reactive nitrogen compounds to investigate the mechanisms by stereochemical means:a) Retention on phosphorus occurs in the amination with O-(mesitylsulfonyl)hydroxylamine consistent with a Ssu