4455-77-0

Usage

Uses

Used in Chemical Synthesis:
(METHOXYMETHYL)DIPHENYLPHOSPHINE OXIDE is used as a catalyst for Molybdenum hexacarbonyl-mediated Pauson-Khand reactions, which are important for the synthesis of complex organic molecules, particularly in the pharmaceutical and agrochemical industries. Its application reason is to facilitate the formation of cyclopentenones from alkynes and an alkylidyne carbene complex.
(METHOXYMETHYL)DIPHENYLPHOSPHINE OXIDE is also used as a catalyst in Rhodium-catalyzed hydroformylation reactions, which involve the conversion of alkenes to aldehydes in the presence of carbon monoxide and hydrogen. This process is crucial in the production of various chemicals, including those used in the manufacturing of plastics, solvents, and detergents. The application reason for its use in this context is to enhance the selectivity and efficiency of the hydroformylation process, leading to the desired aldehyde products with minimal byproducts.

InChI:InChI=1/C14H15O2P/c1-16-12-17(15,13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-11H,12H2,1H3

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 65567-06-8 lithium diphenylphosphide 
• 603-35-0 triphenylphosphine 
• 33670-32-5 methoxymethyltriphenylphosphonium bromide 
• 791-28-6 Triphenylphosphine oxide 
• 1079-66-9 chloro-diphenylphosphine 
• 625-45-6 2-methoxyacetic acid 
• 4559-70-0 Diphenylphosphine oxide 
• 109-87-5 Dimethoxymethane 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 50443-21-5 methoxymethyl-triphenyl-phosphonium cation 

Downstream Products

• 64304-79-6 1-Diphenylphosphinoylmethoxymethyl-cyclohexan-1-ol 
• 43139-94-2 methoxymethylenediphenylphosphine 
• 19096-89-0 methoxymethylenecyclohexane 
• 112419-99-5 (Z)-(2R,3R,4S)-1,3,4-tribenzyloxy-6-methoxyhex-5-en-2-ol 
• 112420-00-5 (E)-(2R,3R,4S)-1,3,4-tribenzyloxy-6-methoxyhex-5-en-2-ol 
• 129143-85-7 3-(2-methoxymethylenecyclohexyl)prop-1-ene 
• 166877-98-1 2-diphenylphosphinoyl-2-methoxy-1-(1-phenylcyclopropyl)ethanol 
• 1028282-19-0 2-(Diphenyl-phosphinoyl)-2-methoxy-1-(1-phenyl-cyclohexyl)-ethanol 
• 135942-77-7 {5-tert-Butyl-2-[1-methoxy-meth-(Z)-ylidene]-cyclohexylsulfanyl}-benzene 
• 1026951-05-2 2-(Diphenyl-phosphinoyl)-2-methoxy-1-(1-phenyl-cyclobutyl)-ethanol 

Relevant academic research and scientific papers

Dearylation of arylphosphine oxides using a sodium hydride-iodide composite

A new protocol for the dearylation of arylphosphine oxides was developed using sodium hydride (NaH) in the presence of lithium iodide (LiI). The transient sodium phosphinite could be functionalized with a range of electrophiles in a one-pot fashion.

METHOD FOR THE MANUFACTURE OF COMPOUNDS CONTAINING AN ALPHA-OXY PHOSPHORUS GROUP BY USING P-X COMPONENTS

A method for the manufacture of compounds containing an α- oxy phosphorus group is disclosed. A P-X component having at least one P-X bond, whereby the phosphorus of the P-X bond has the +3 oxidation state with X being C1 or Br, is reacted in a specific equivalent ratio with a compound containing an α-oxy carboxylic acid group, followed by conducting the reaction and optionally adding a quenching agent at the end of the reaction. The compounds containing an α-oxy phosphorus group formed are then recovered.

METHOD FOR THE MANUFACTURE OF COMPOUNDS CONTAINING AN α-OXY PHOSPHORUS GROUP

A method for the manufacture of compounds containing an α-oxy phosphorus group is disclosed. A P-O component having at least one P-O-P moiety, whereby at least one phosphorus has the +3 oxidation state, is added in specific proportions to a compound containing an α-oxy carboxylic acid group, followed by conducting the reaction and adding water subsequently. The compounds containing an α-oxy phosphorus group formed can then be recovered.

Effect of base on alkyltriphenylphosphonium salts in polar aprotic solvents

When arylmethyl phosphonium salts are treated with a base (e.g., t-BuOK or NaH) they homocouple to form symmetric 1,2-diarylethenes. In some cases, dilution and (or) use of excess base lead to very high yields of the product. This reaction is solvent sensitive: the reaction occurs only when polar aprotic solvents such as acetonitrile or DMSO are used. Other alkyl phosphonium salts (e.g., ethoxycarbonylmethyltriphenylphosphonium bromide and n- butyltriphenylphosphonium bromide) form a ylid (when an α-carbonyl group is present) or lose a phenyl group to form alkyldiphenylphosphine oxides when treated with the base. Mechanistic investigation of the homocoupling reaction indicates that the reaction proceeds through a ylid that acts as a nucleophile on an unreacted phosphonium salt. The resulting adduct undergoes elimination to form the observed product. The EIZ ratio seems to depend on the amount of the base used and the phosphonium salt involved.

Thermolyses of α-phosphorylmethyl tetrazolyl sulfoxides in the presence of 2,3-dimethyl-1,3-butadiene and their reactions with several amines

We have synthesized α-(phosphoryl)methyl tetrazolyl sulfoxides and examined the reactivities in the thermolyses and in the presence of several amines, such as aniline, benzylamine, piperidine, pyrrolidine, and morpholine. Thermolyses of the derivatives in the presence of 2,3-dimethyl-1,3-butadiene afforded 2-phosphoryl substituted 4,5-dimethyl-3,6-dihydro-2H-thiopyran S-oxide. In addition, novel phosphinecarbothioamides were obtained in the reaction of the derivatives with amines.

PREPARATION OF α-OXYGENATED PHOSPHINE OXIDES FROM CHLORODIPHENYLPHOSPHINE

A range of α-alkoxyphosphine oxides, including novel α-methoxyallyl oxides, are readily prepared from chlorodiphenylphosphine and acetals.