71893-27-1

Basic information

• Product Name: 2-Butanone, 3-(diphenylphosphinyl)-
• CAS NO: 71893-27-1
• Molecular Formula: C16H17O2P
• Molecular Weight: 272.284
• Mol File: 71893-27-1.mol

Chemical Properties

• CAS DataBase Reference: 2-Butanone, 3-(diphenylphosphinyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butanone, 3-(diphenylphosphinyl)-(71893-27-1)
• EPA Substance Registry System: 2-Butanone, 3-(diphenylphosphinyl)-(71893-27-1)

Safety Data

• Hazardous Substances Data: 71893-27-1(Hazardous Substances Data)

Upstream product

• 24630-80-6 diphenylphosphine oxide 
• 141-78-6 ethyl acetate 
• 1733-57-9 ethydiphenylphosphine oxide 
• 1733-52-4 1-(diphenylphosphinoyl)propan-2-one 
• 74-88-4 methyl iodide 

Downstream Products

• 87710-55-2 ethyl 3-diphenylphosphinoyl-3-methyl-4-oxopentanoate 
• 50356-83-7 (1-methyl-4-oxopent-2-yl)diphenylphosphine oxide 
• 821770-43-8 (E)-2-diphenylphosphinoyl-7-phenyl-hept-6-en-3-one 
• 1219594-33-8 2-[1-(diphenylphosphoryl)ethyl]-1,6-naphthyridine 
• 103785-70-2 (R*,S*)-3-Diphenylphosphinoylbutan-2-ol 
• 103785-70-2 (R*,R*)-3-Diphenylphosphinoylbutan-2-ol 

Relevant articles and documents

Friedl?nder reaction in the synthesis of 2-(phosphoryl)alkyl-substituted 1,6-naphthyridines

First 2-(phosphoryl)alkyl-substituted 1,6-naphthyridines have been synthesized by the Friedl?nder reaction between 4-amino-3-formylpyridine and phosphorus-containing ketones; their structures have been confirmed by 1H, 13C and 31P NMR spectroscopy and X-r

Diphenylphosphinoyl-mediated synthesis of ketones

α-Diphenylphosphinoyl ketones are selectively and sequentially alkylated at the α-position. Double lithiation and selective alkylation occurs at the less stabilised γ-position. Dephosphinoylation of the alkylation products gives ketones. Mono-alkylation is selective, highly crystalline intermediates are formed and a one-pot strategy is possible. The method is ideally suited for the preparation of acid-sensitive ketones. The Royal Society of Chemistry 2006.

Opposite stereochemical effects exerted by CeCl3 and TiCl4 on the Lewis acid mediated reduction of α-alkyl-β-ketophosphine oxides with metallic hydrides: A highly stereoselective protocol for the synthesis of syn and anti α-alkyl-β-hydroxyphosphine oxides

A general, highly efficient methodology for obtaining both syn and anti α-hydroxyphosphine oxides by reduction of the corresponding α-ketophosphine oxides is described. The nature of the Lewis acid was found to be pivotal in determining the outcome of these reactions. Strongly chelating TiCl4 led to the anti isomer in high diastereoisomeric excess in noncoordinating solvents (CH2Cl2) at -78°C with BH3/py as reducing agent, while nonchelating CeCl3 gave a high excess of the syn isomer in coordinating solvents (THF) at the same temperature with LiBH4 as reducing agent. In the latter case, CeCl3 is essential in achieving high yields and stereoselectivity, since it allows the reaction to be performed at low temperatures. Otherwise, higher temperatures (0 °C) are required, which lower both yields and selectivities. Moreover, each step of the protocol for the synthesis of stereodefined disubstituted olefins from alkylphosphine oxides (Warren's modification of the Homer procedure) has been optimized, and the optimized procedure has been applied to the synthesis of muscalure, the pheromone of the domestic fly.

Reactions of Anions from α-Diphenylphosphinoyl Ketones with Electrophiles

Anions from α-Ph2P(O)-ketones do not give Horner-Wittig reactions but do react with alkyl halides, including α-halogenocarbonyl compounds, and Michael acceptors.The products may be stereoselectively reduced.