99364-92-8

Basic information

• Product Name: Phosphine, (phenylmethylene)[2,4,6-tris(1,1-dimethylethyl)phenyl]-, (1E)-
• CAS NO: 99364-92-8
• Molecular Formula: C25H35P
• Molecular Weight: 366.527
• Mol File: 99364-92-8.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Phosphine, (phenylmethylene)[2,4,6-tris(1,1-dimethylethyl)phenyl]-, (1E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphine, (phenylmethylene)[2,4,6-tris(1,1-dimethylethyl)phenyl]-, (1E)-(99364-92-8)
• EPA Substance Registry System: Phosphine, (phenylmethylene)[2,4,6-tris(1,1-dimethylethyl)phenyl]-, (1E)-(99364-92-8)

Safety Data

• Hazardous Substances Data: 99364-92-8(Hazardous Substances Data)

Upstream product

• 86120-24-3 (2,4,6-tri-tert-butyl)phenylmonochlorophosphane 
• 83115-12-2 (2,4,6-tri-tert-butylphenyl)phosphine 
• 100-52-7 benzaldehyde 
• 91425-17-1 (2,4,6-tri-tert-butylphenyl)(trimethylsilyl)phosphane 
• 68357-98-2 mesitylphosphine 
• 79074-00-3 2,4,6-tri-t-butylphenylphosphonous dichloride 
• 212079-68-0 [(2,4,6-tri-tert-butylphenyl)PPMe₃] 
• 100281-31-0 (E/Z)-(Bromomethylene)(2,4,6-tri-tert-butylphenyl)phosphane 
• 100-58-3 phenylmagnesium bromide 
• 100-59-4 phenylmagnesium chloride 
• 92957-42-1 E-2-chloro-1-(2,4,6-tri-t-butylphenyl)-1-phospha-ethylene 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 88721-97-5 lithium (t-butyldimethylsilyl)(2,4,6-tri-t-butylphenyl)phosphide 
• 88721-96-4 t-butyldimethylsilyl(2,4,6-tri-t-butylphenyl)phosphine 

Downstream Products

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 107394-70-7 2,4,6-tri-tert-butylphenylphosphinic acid 
• 156754-78-8 Cu₂Cl₂(CH₃CN)2(P(C₆H₂(C(CH₃)3)3)CHC₆H₅)2 
• 102150-16-3 (Phenylethenyliden)(2,4,6-tri-tert-butylphenyl)phosphan 
• 129715-34-0 (1S,3S)-2,2-Dichloro-3-phenyl-1-(2,4,6-tri-tert-butyl-phenyl)-phosphirane 
• 100281-24-1 2,2-dichloro-1-(2,4,6-tri-tert-butylphenyl)-1-phosphaethene 

Relevant articles and documents

The Phospha-Bora-Wittig Reaction

We report the phospha-bora-Wittig reaction for the direct preparation of phosphaalkenes from aldehydes, ketones, esters, or amides. The transient phosphaborene Mes*P═B-NR2 reacts with carbonyl compounds to form 1,2,3-phosphaboraoxetanes, analogues of oxap

Unsymmetrical E-Alkenes from the Stereoselective Reductive Coupling of Two Aldehydes

The unprecedented formation of unsymmetrical alkenes from the intermolecular reductive coupling of two different aldehydes is described. In contrast to the McMurry reaction which affords statistical product mixtures, selectivity in the reported procedure is achieved by a sequential ionic mechanism in which a first aldehyde is reacted with a phosphanylphosphonate to afford a phosphaalkene intermediate which, upon activation by hydroxide, reacts with a second aldehyde to the unsymmetrical E-alkenes. The described reaction is free of transition metals and proceeds under ambient temperature within minutes in good to excellent overall yields. It is a new methodology to use feedstock aldehydes for the direct production of C C double bond-containing products and may impact how chemists think of multistep synthetic sequences in the future.

The synthetic potential of C-halophosphaalkenes

Methodologies for the functionalization of phosphaalkenes Mes*P=CHal2 were developed. Lithiation with n-butyllithium yielded carbenoids Mes*P=CLiHal which were reacted with various electrophiles such as acid chlorides, carbonyl compounds, and metal halides. The dihalophosphaalkenes were also converted to monohalophosphaalkenes; the latter proved to be suitable for Stille-type cross coupling reaction with Grignard reagents. New phosphaalkenes of the type (E)-Mes*P=C(H)Ar with a variety of functionalities were obtained in high yield and isomeric purity.