15935-94-1

Basic information

• Product Name: Allylidenetriphenylphosphorane
• Synonyms: allylidenetriphenylphosphorane;Allylenetriphenylphosphorane;Triphenyl-2-propenylidenephosphorane;Triphenylpropenylidenephosphorane;Vinylmethylenetriphenylphosphorane
• CAS NO: 15935-94-1
• Molecular Formula: C₂₁H₁₉P
• Molecular Weight: 302.35
• Mol File: 15935-94-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 452.3 °C at 760 mmHg
• Flash Point: 227.3 °C
• Appearance: /
• Density: 1.09
• CAS DataBase Reference: Allylidenetriphenylphosphorane(CAS DataBase Reference)
• NIST Chemistry Reference: Allylidenetriphenylphosphorane(15935-94-1)
• EPA Substance Registry System: Allylidenetriphenylphosphorane(15935-94-1)

Safety Data

• Hazardous Substances Data: 15935-94-1(Hazardous Substances Data)

Usage

General Description

Allylidenetriphenylphosphorane is a chemical compound with the molecular formula C18H15P. It is a yellow crystalline solid with a melting point of 146-147°C. Allylidenetriphenylphosphorane is commonly used as a reagent in organic synthesis, specifically as a Wittig reagent for the preparation of alkenes from aldehydes and ketones. It reacts with carbonyl compounds to form the corresponding alkenes in a reaction known as the Wittig reaction. Allylidenetriphenylphosphorane is an important building block in the production of various pharmaceuticals, perfumes, and flavors, and it is widely used in research and industrial processes in the chemical industry. Allylidenetriphenylphosphorane should be handled with care, as it is a flammable and potentially hazardous substance.

Upstream product

• 603-35-0 triphenylphosphine 
• 109-72-8 n-butyllithium 
• 1560-54-9 allyltriphenylphosphonium bromide 
• 591-51-5 phenyllithium 
• 865-47-4 potassium tert-butylate 
• 18480-23-4 allyltriphenylphosphonium chloride 

Downstream Products

• 135712-27-5 N-buta-1,3-dienyl-N-methyl-aniline 
• 116384-36-2 (1R,2R,3S,3aR,7aS)-1,2,3-Tris-benzyloxy-2,3,3a,4,5,7a-hexahydro-1H-indene 
• 84673-82-5 triphenylphosphorane 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 18304-14-8 (E)-6-methyl-1,3,5-heptatriene 
• 64586-03-4 (Z)-6-methyl-1,3,5-heptatriene 
• 41793-01-5 4,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehyde 
• 94477-85-7 trans-1,2-Diphenyl-4-(triphenylphosphoranyliden)bicyclo<3.1.0>hexan-3-on 
• 145013-11-2 1,4-Bis-((E)-buta-1,3-dienyl)-benzene 
• 29837-19-2 (3E,5Z,8Z)-1,3,5,8-undecatetraene 
• 125153-26-6 [((Z)-1-Buta-1,3-dienyl)-heptylsulfanyl]-benzene 
• 125153-25-5 [((E)-1-Buta-1,3-dienyl)-heptylsulfanyl]-benzene 
• 116498-64-7 (2R,3S,4R)-tribenzyloxy-octa-5(Z),7-diene-1-al diethyl dithioacetal 

Relevant articles and documents

One-pot synthesis of 1-pentafluorophenyl-1,3-dienes

Perfluorobenzene was added to allylidenetriphenylphosphorane regiospecifically, after transylidation, to give (3-pentafluorophenyl)allylidenetriphenylphosphorane, which reacted with aldehydes to afford 1-pentafluorophenyl-1,3-dienes in good to excellent y

Free radical cyclizations of trienes with tris(trimethylsisyl)silane

The intramolecular trapping of a stabilized intermediate allylic radical generated by the addition of tris(trimethylsilyl)silyl (sisyl) radical to a conjugated system was performed. The observed low stereoselectivity suggests thermodynamic rather than kinetic control in this cyclization process.

Heavier Carbonyl Olefination: The Sila-Wittig Reaction

The Wittig reaction is one of the most versatile tools in the repertoire of organic chemists. Thus, a broad variety of carbonyl compounds can be converted to tailor-made alkenes with phosphorus ylides under mild conditions. However, no comparable reaction has been reported for silanones, the silicon congeners of ketones. Here, we demonstrate for the first time the successful application of the Wittig olefination to iminosilylsilanone 1. The selective formation of a series of silenes (R2Sia? CR2) via the sila-Wittig reaction revealed an unprecedented approach to otherwise elusive compounds. In addition, the highly reactive and zwitterionic nature of 1 was also susceptible to nucleophilic attacks and cycloaddition reactions by and with the phosphorus ylides. Our results therefore make another important contribution to discovering the differences and similarities between carbon and silicon.