5405-63-0

Basic information

• Product Name: Triphenylphosphine,1,4-benzoquinone adduct
• Synonyms: Triphenylphosphine,1,4-benzoquinone adduct;Triphenylphosphine-1,4-benzoquinone adduct (TPP-BQ);4-Hydroxy-2-(triphenylphosphonium)phenolate;(2,5-Dihydroxyphenyl)-triphenyl-phosphanium
• CAS NO: 5405-63-0
• Molecular Formula: C₂₄H₁₉O₂P
• Molecular Weight: 371.388161
• Mol File: 5405-63-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Triphenylphosphine,1,4-benzoquinone adduct(CAS DataBase Reference)
• NIST Chemistry Reference: Triphenylphosphine,1,4-benzoquinone adduct(5405-63-0)
• EPA Substance Registry System: Triphenylphosphine,1,4-benzoquinone adduct(5405-63-0)

Safety Data

• Hazardous Substances Data: 5405-63-0(Hazardous Substances Data)

Usage

General Description

Triphenylphosphine,1,4-benzoquinone adduct is a chemical compound formed by the addition of triphenylphosphine to 1,4-benzoquinone. The adduct is a yellow to orange crystalline solid that is often used as a reagent in organic synthesis. It is commonly used in the preparation of various classes of organic compounds, including pharmaceuticals, agrochemicals, and materials. The compound is known for its ability to act as a nucleophile and undergo a range of reactions, such as Michael addition, Wittig reaction, and Diels-Alder reaction, making it a versatile tool for organic chemists. Additionally, the adduct has been studied for its potential applications in the development of new materials and catalytic systems due to its unique chemical properties.

InChI:InChI=1/C24H19O2P/c25-19-16-17-23(26)24(18-19)27(20-10-4-1-5-11-20,21-12-6-2-7-13-21)22-14-8-3-9-15-22/h1-18H,(H-,25,26)/p+1

Upstream product

• 603-35-0 triphenylphosphine 
• 106-51-4 p-benzoquinone 
• 71-43-2 benzene 

Downstream Products

• 58359-73-2 (2,5-dihydroxy-phenyl)-triphenyl-phosphonium; chloride 
• 131523-63-2 2-(triphenylbromophosphonio)-5-bromo-1,4-hydroquinone 
• 104574-60-9 Ni(C₆H₅)((C₆H₅)3P)((C₆H₅)2P(C₆H₃OH)O) 

Relevant articles and documents

Interactions of tertiary phosphines with p-benzoquinones; X-ray structures of [HO(CH2)3]3P+C6H 2(O-)(OH)(MeO) and Ph3P+C 6H3(O-)(OH)

Phosphonium zwitterions of a known type were obtained in high yield via a 1:1 reaction of p-benzoquinone or methoxy-p-benzoquinone with the tertiary phosphines R3P [R = (CH2)3OH, Ph, Et, Me] and Ph2MeP, in acetone or benzene at room temperature. In all cases, attack of the P-atom occurs at a C-atom rather than at an O-atom. The products were characterized to various degrees by elemental analysis, 31P{1H}, 1H and 13C NMR spectroscopies, and mass spectrometry, and two of the zwitterions, the new [HO(CH2)3]3P+C6H 2(O-)(OH)(MeO) and the known Ph3P +C6H3(O-)(OH), were structurally characterized by X-ray analysis. The PEt3 reaction also produces small amounts of the 'dimeric', μ-oxo co-product Et3P +C6H2(O-)(OH)-O-C6H 3(O-)P+Et3 that is tentatively characterized by 1D- and 2D-NMR data. 2,5-Di-tert-butyl- and 2,3,5,6-tetramethyl-p-benzoquinone do not react with [HO(CH2) 3]3P under the conditions noted above. Heating D 2O solutions of the water-soluble zwitterions R3P +C6H3(O-)(OH) [R = (CH 2)3OH, Et] at 90 °C for 72 h leads to complete H/D exchange of the H-atom in the position ortho to the phosphonium center.

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