35752-46-6

Basic information

• Product Name: Acetic acid, phosphono-, 1-ethyl ester
• Synonyms: Acetic acid,phosphono-,1-ethyl ester;Phosphonoessigsaeure-C-aethylester;ethoxycarbonylmethyl-phosphonic acid;phosphonoacetic acid-triethyl ester;Aethoxycarbonylmethyl-phosphonsaeure;Essigsaeureaethylester-phosphonsaeure;ethyl phosphonoacetate;PHOSPHONOACETIC ACID ETHYL ESTER
• CAS NO: 35752-46-6
• Molecular Formula: C4H9O5P
• Molecular Weight: 168.086
• Mol File: 35752-46-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 334.8±44.0 °C(Predicted)
• Density: 1.434±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Acetic acid, phosphono-, 1-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, phosphono-, 1-ethyl ester(35752-46-6)
• EPA Substance Registry System: Acetic acid, phosphono-, 1-ethyl ester(35752-46-6)

Safety Data

• Hazardous Substances Data: 35752-46-6(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 4408-78-0 phosphonoacetic acid 
• 311-46-6 ethyl 2-(dimethoxyphosphoryl)acetate 
• 67-56-1 methanol 
• 65868-40-8 ethyl P,P-bis(trimethylsilyl) phosphonoacetate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 51656-91-8 ethyl 1,4-dioxaspiro[4,5]dec-8-ylideneacetate 
• 20583-78-2 ethyl (E)-3,4-dimethoxycinnamate 
• 24398-80-9 ethyl 3-bromo-cinnamate 
• 117626-87-6 Sodium; {[(2R,3S,4S,5R)-5-(5-acetyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetate 
• 4408-78-0 phosphonoacetic acid 

Relevant articles and documents

The mckenna reaction – avoiding side reactions in phosphonate deprotection

The McKenna reaction is a well-known and popular method for the efficient and mild synthesis of organophosphorus acids. Bromotrimethylsilane (BTMS) is the main reagent in this reaction, which transforms dialkyl phosphonate esters into bis(trimethylsilyl)esters, which are then easily converted into the target acids. However, the versatile character of the McKenna reaction is not always used to its full extent, due to formation of side products. Herein, demonstrated by using model examples we have not only analyzed the typical side processes accompanying the McKenna reaction, but also uncovered new ones. Further, we discovered that some commonly recommended precautions did not always circumvent the side reactions. The proposed results and recommendations may facilitate the synthesis of phosphonic acids.

Dealkylation of dialkyl phosphonates with boron tribromide

Boron tribromide cleanly and quantitatively converts dimethyl-, diethyl-, diisopropyl-, and ditertiobutyl phosphonates RP(O)(OR')2 into the corresponding phosphonic acids RP(O)(OH)2 via methanolysis. The use of boron tribromide is compatible with a variety of functionalities in the R group.

ORGANOPHOSPHORUS COMPOUNDS AS ANTIVIRAL AGENTS

The 5'-triphosphates of 2'-5' linked oligoadenylic acids are formed in cells which have been exposed to interferon and may be involved in the antiviral activity of the latter.The lead(II) ion-catalysed oligomerisation of adenosin 5'-phosphorimidazolidate is a convenient route for the preparation of the 5'-phosphates of 2'-5' linked oligoadenylic acids.The latter can readily be converted to the triphosphates or coupled to the 5'-phosphate of nicotinamide nucleoside to give naturally occurring pyrophosphates which may act as reservoirs for the oligoadenylic acids in cells.Pyrophosphate analoques, eg. phophonoacetic and phosphonoformic acids or carbon-substituted methylenebisphosphonic acids are antiviral agents of potential commercial interest as they inhibit the replication of a number of viruses including herpes and influenza.These pyrophosphate analogues do not appear to inhibit virus replication by being incorporated into nucleoside triphosphates which block nucleic acid synthesis.Rather analogues appear to act by forming stable complexes with an essential metal ion (probably zinc) at the active sites of nucleic acid polymerases of viruses.