53359-85-6

Basic information

• Product Name: tetraethyl 2-(4-nitrophenyl)ethene-1,1-diyldiphosphonate
• Synonyms: tetraethyl 2-(4-nitrophenyl)ethene-1,1-diyldiphosphonate
• CAS NO: 53359-85-6
• Molecular Weight: 421.324
• Mol File: 53359-85-6.mol

Chemical Properties

• CAS DataBase Reference: tetraethyl 2-(4-nitrophenyl)ethene-1,1-diyldiphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: tetraethyl 2-(4-nitrophenyl)ethene-1,1-diyldiphosphonate(53359-85-6)
• EPA Substance Registry System: tetraethyl 2-(4-nitrophenyl)ethene-1,1-diyldiphosphonate(53359-85-6)

Safety Data

• Hazardous Substances Data: 53359-85-6(Hazardous Substances Data)

Upstream product

• 1660-94-2 Tetraethyl methylenediphosphonate 
• 555-16-8 4-nitrobenzaldehdye 
• 4231-16-7 1-(p-nitrophenyl)-2-nitro-1-propene 

Downstream Products

• 1315613-65-0 (2S,3R)-methyl 2-amino-4,4-bis(diethoxyphosphoryl)-3-(4-nitrophenyl)butanoate 

Relevant articles and documents

Challenging synthesis of bisphosphonate derivatives with reduced steric hindrance

An alternative approach is reported for the synthesis of methyl ester protected bisphosphonate building blocks, such as methylene bisphosphonate, vinylidenebisphosphonate and aryl substituted prochiral vinylidenebisphosphonates, that cannot be obtained directly from dimethyl phosphite and dichloromethane.

A Facile Cu(I)/TF-BiphamPhos-catalyzed asymmetric approach to unnatural α-amino acid derivatives containing gem-bisphosphonates

A novel catalytic asymmetric Michael addition of azomethine ylide with β-substituted alkylidene bisphosphates was realized in the presence of a chiral copper(I)/TF-BiphamPhos complex. The present system provides a unique and facile access to enantioenriched unnatural α-amino acid derivatives containing gem-bisphosphonates (gem-BPs) in high yields with excellent diastereoselectivities and enantioselectivities. Subsequent transformations lead to the expedient preparation of biologically active unnatural α-amino acid derivatives containing BPs and bisphosphonic acids without loss of diastereo- and enantiomeric excess.

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS 62. REACTIONS OF METHYLENEBISPHOSPHONATE WITH α-NITROALKENES. A NOVEL SYNTHESIS OF ETHENYLIDENEBISPHOSPHONATES AND 2-ISOXAZOLINE-5,5-DIYLBISPHOSPHONATES

Reaction of methylenebisphosphonate with α-nitroalkenes followed by addition of trimethylchlorosilane leads to the formation of ethenylidenebisphosphonates and trimethylsilyl nitronate in almost quantitative yield.These two products, upon prolonged reaction at ambient temperature, provide 2-isoxazoline-5,5-diylbisphosphonates via regioselective 1,3-dipolar cycloaddition in high yield.Key words: Methylenebisphosphonate; α-nitroalkenes; ethenylidenebisphosphonate; 2-isoxazoline-5,5-diylbisphosphonate; 1,3-dipolar cycloaddition.