20435-05-6

Basic information

• Product Name: Phosphoric acid, cyanophenylmethyl diethyl ester
• CAS NO: 20435-05-6
• Molecular Formula: C12H16NO4P
• Molecular Weight: 269.237
• Mol File: 20435-05-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Phosphoric acid, cyanophenylmethyl diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid, cyanophenylmethyl diethyl ester(20435-05-6)
• EPA Substance Registry System: Phosphoric acid, cyanophenylmethyl diethyl ester(20435-05-6)

Safety Data

• Hazardous Substances Data: 20435-05-6(Hazardous Substances Data)

Upstream product

• 3277-27-8 diethyl benzoylphosphonate 
• 151-50-8 potassium cyanide 
• 2408-36-8 lithium cyanide 
• 100-52-7 benzaldehyde 
• 814-49-3 diethyl chlorophosphate 
• 2942-58-7 diethyl cyanophosphonate 

Downstream Products

• 5087-17-2 4'-chlorobenzoin 
• 123346-56-5 Phosphoric acid 1-(4-chloro-phenyl)-2-cyano-2-hydroxy-2-phenyl-ethyl ester diethyl ester 
• 20907-27-1 2-hydroxy-2-methyl-1-phenyl-3-buten-1-one 
• 123346-73-6 2-diethylphosphonooxy-2-methyl-1-phenyl-3-buten-1-one 
• 123346-74-7 5-cyano-5-diethylphosphonooxy-5-phenylpentan-2-one 
• 88151-72-8 1-(Diethylphosphonooxy)-2-phenylpropanenitrile 
• 88151-73-9 2-diethylphosphonooxy-2-phenylbutanenitrile 
• 123346-59-8 Phosphoric acid 2-cyano-2-hydroxy-1-(4-methoxy-phenyl)-2-phenyl-ethyl ester diethyl ester 
• 34904-93-3 2-Hydroxy-2-(3-methoxyphenyl)-1-phenylethanone 
• 123346-75-8 (Z)-ethyl-2-cyano-1-methyl-2-phenylcyclopropanecarboxylate 
• 123360-87-2 2-diethylphosphonooxy-2,3-diphenylpropanenitrile 
• 123360-88-3 Phosphoric acid 2-cyano-2-hydroxy-2-phenyl-1-p-tolyl-ethyl ester diethyl ester 
• 123346-67-8 α-diethylphosphonooxycyclohexyl phenyl ketone 
• 140-29-4 phenylacetonitrile 

Relevant articles and documents

A convenient and improved preparation of Cyano phosphates

Cyano phosphates derived from aldehydes or ketones are prepared in good yields using lithium cyanide in DMF and diethyl chlorophosphate as phosphorylating agent.

Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates

Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.

Cyano-phosphorylation of aldehydes catalyzed by a nucleophilic N-heterocyclic carbene

The first method for cyano-phosphorylation of aldehydes with diethyl cyanophosphonate in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and KOt-Bu, as a nucleophilic catalyst, is described.