4455-75-8

Basic information

• Product Name: (2-methylprop-2-en-1-yl)(diphenyl)phosphane oxide
• CAS NO: 4455-75-8
• Molecular Formula: C₁₆H₁₇OP
• Molecular Weight: 256.2793
• Mol File: 4455-75-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 351.9°C at 760 mmHg
• Flash Point: 166.6°C
• Density: 1.08g/cm³
• Vapor Pressure: 8.09E-05mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: (2-methylprop-2-en-1-yl)(diphenyl)phosphane oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (2-methylprop-2-en-1-yl)(diphenyl)phosphane oxide(4455-75-8)
• EPA Substance Registry System: (2-methylprop-2-en-1-yl)(diphenyl)phosphane oxide(4455-75-8)

Safety Data

• Hazardous Substances Data: 4455-75-8(Hazardous Substances Data)

Usage

General Description

The chemical (2-methylprop-2-en-1-yl)(diphenyl)phosphane oxide is a phosphorus-based compound with the molecular formula C17H17OP. It is a phosphane oxide that consists of a phosphorus atom bonded to two phenyl groups and a (2-methylprop-2-en-1-yl) group. (2-methylprop-2-en-1-yl)(diphenyl)phosphane oxide is commonly used as a ligand in organometallic chemistry and catalysis. It is known for its ability to coordinate with metal ions and facilitate various chemical reactions. Additionally, it has been studied for its potential applications in organic synthesis and material science. Overall, (2-methylprop-2-en-1-yl)(diphenyl)phosphane oxide plays a significant role in the field of coordination chemistry and has diverse applications in various research and industrial settings.

Upstream product

• 3756-30-7 1-iodo-2-methyl-2-propene 
• 719-80-2 Ethyl diphenylphosphinite 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 1499-21-4 Diphenylphosphinic chloride 
• 603-35-0 triphenylphosphine 
• 1079-66-9 chloro-diphenylphosphine 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 35078-75-2 (2-hydroxy-2-methylpropyl)diphenylphosphine oxide 
• 1026594-12-6 C₁₆H₁₇OP 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 4559-70-0 Diphenylphosphine oxide 
• 117924-17-1 [2-(Diphenyl-phosphinoyl)-1,1-dimethyl-ethoxy]-trimethyl-silane 
• 3017-69-4 2-methyl-1-propenylbromide 
• 13172-76-4 diphenyl(propa-1,2-dien-1-yl)phosphine oxide 

Downstream Products

• 58093-12-2 C₁₉H₂₁OP 
• 194038-43-2 1-bromo-2-(methyldiphenylphosphinoyl)-2-propene 
• 126338-52-1 (2R,3R)-3-(Diphenyl-phosphinoyl)-1-hydroxy-2-methyl-5,5-bis-phenylsulfanyl-heptan-4-one 
• 126338-51-0 (1S,2R,3R)-2-(Diphenyl-phosphinoyl)-3-methyl-1-(1-phenylsulfanyl-cyclohexyl)-butane-1,4-diol 
• 126338-50-9 (2R,3R,4S)-3-(Diphenyl-phosphinoyl)-5-ethyl-2-methyl-5-phenylsulfanyl-heptane-1,4-diol 
• 126338-47-4 (3S,4S)-3-(Diphenyl-phosphinoyl)-4-methyl-2-(2-methyl-[1,3]dithiolan-2-yl)-tetrahydro-furan-2-ol 
• 126338-46-3 2-Methyl-[1,3]dithiolane-2-carboxylic acid 3-(diphenyl-phosphinoyl)-2-methyl-propyl ester 
• 126338-48-5 (1S,2R,3R)-2-(Diphenyl-phosphinoyl)-3-methyl-1-(2-methyl-[1,3]dithiolan-2-yl)-butane-1,4-diol 
• 147701-15-3 3-diphenylphosphinoyl-2-methyl-1-triphenylmethoxypropane 

Relevant articles and documents

Copper-Catalyzed C?P Cross-Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with in situ Halogen Exchange

An efficient protocol for concurrent tandem halogen exchange/C?P cross-coupling of cycloalkenyl bromides and secondary phosphine oxides has been developed. The catalytic system is based on cheap and air-stable copper(I) iodide as the precatalyst, commercially available N,N’-dimethylethylenediamine as the ligand, and Cs2CO3 or K2CO3 as the base. The use of sodium iodide as an additive reduces the excessive use of organic bromides to near-stoichiometric by promoting the in situ transformation to the corresponding iodides. Diarylphosphine oxides undergo cycloalkenylation with 35–99 % yields and dicyclohexylphosphine oxide with 30–53 % yields. In the case of acyclic alkenyl bromides the cross-coupling products undergo conjugate addition of diphenylphosphine oxide and satisfying yields are observed only for internal olefins. In the case of aryl bromides satisfying yields (43–72 %) are observed only for sterically unhindered arenes or arenes possessing an ortho-directing group. Cycloalkenylphosphine oxides prepared in the cross-coupling reaction undergo base-catalyzed and base-promoted conjugate addition to give bis(phosphinoyl)cycloalkanes.

Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes

The stereocontrolled synthesis of trans-disubstituted cyclopropylketones has been achieved from β-alkyl, γ-benzoyl phosphine oxides via a three-step cascade reaction incorporating an acyl transfer, phosphinoyl transfer and cyclisation to form the cyclopropane. Using Evans' chiral oxazolidinone auxiliary and by masking the phosphine oxide moiety as a phosphine borane we have extended the method to the synthesis of enantiomerically-enriched trans-disubstituted cyclopropyl ketones.

Synthesis of a functionalized allylic phosphine oxide

A functionalized allylic phosphine oxide has been prepared by regioselective bromination of 2-(methyldiphenylphosphinoyl)-1-propene followed by nucleophilic substitution with acetate. Hydrolysis and protection yielded the target compound.