5954-28-9

Basic information

• Product Name: Phosphoric acid 1-methylvinyldiethyl ester
• Synonyms: Phosphoric acid 1-methylvinyldiethyl ester;Phosphoric acid diethylisopropenyl ester;Phosphoric acid diethyl ester isopropenyl ester
• CAS NO: 5954-28-9
• Molecular Formula: C₇H₁₅O₄P
• Molecular Weight: 194.1654
• Mol File: 5954-28-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 200.3°Cat760mmHg
• Flash Point: 89.2°C
• Appearance: /
• Density: 1.065g/cm³
• Vapor Pressure: 0.463mmHg at 25°C
• Refractive Index: 1.42
• CAS DataBase Reference: Phosphoric acid 1-methylvinyldiethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid 1-methylvinyldiethyl ester(5954-28-9)
• EPA Substance Registry System: Phosphoric acid 1-methylvinyldiethyl ester(5954-28-9)

Safety Data

• Hazardous Substances Data: 5954-28-9(Hazardous Substances Data)

Usage

Uses

Diethyl Isopropenyl Phosphate can be used for fireproofing porous wallboards.

Synthesis Reference(s)

Tetrahedron Letters, 6, p. 3995, 1965 DOI: 10.1016/S0040-4039(01)99603-0

InChI:InChI=1/C7H15O4P/c1-5-9-12(8,10-6-2)11-7(3)4/h3,5-6H2,1-2,4H3

Upstream product

• 78-95-5 chloroacetone 
• 122-52-1 triethyl phosphite 
• 60-29-7 diethyl ether 
• 598-31-2 1-bromoacetone 
• 3019-04-3 iodoacetone 
• 73519-29-6 diethyl 1-hydroxy-1-methyl-2-chloroethylphosphonate 
• 2724-79-0 tributyltin tert-butoxide 

Downstream Products

• 3309-79-3 phosphoric acid diethyl ester-(1-methyl-2-methylsulfanyl-vinyl ester) 
• 598-02-7 Diethyl phosphate 
• 814-22-2 diethyl n-propyl phosphate 

Relevant articles and documents

Asymmetric hydrogenation of α- Or β-acyloxy α,β- unsaturated phosphonates catalyzed by a Rh(i) complex of monodentate phosphoramidite

The Rh(i) complex of a monodentate phosphoramidite bearing a primary amine moiety (DpenPhos) has been disclosed to be highly efficient for the asymmetric hydrogenation of a variety of α- or β-acyloxy α,β- unsaturated phosphonates, providing the corresponding biologically important chiral α- or β-hydroxy phosphonic acid derivatives with excellent enantioselectivities (90->99% ee).

An efficient separation method for enol phosphate and corresponding β-ketophosphonate from their mixtures under aqueous conditions

Separation of a mixture β-ketophosphonate 3 and their corresponding enol phosphate 4 is efficiently carried out in aqueous alkaline solutions. Enol phosphate 4 is first extracted with hexanes:dichloromethane (19:1). Acidification of the aqueous layer followed by extraction of the β-ketophosphonate 3 with dichloromethane completes the separation. Thus, when 1-bromo-2,4-pentadione la reacted with triethyl phosphite to give diethyl (2,4-dioxopentyl)phosphonate 3a (Arbuzov-product) and the corresponding enol phosphate 4a (Perkow-product), separation of the two compounds was carried out using this method.

Silyl Phosphites. 15. Reactions of Silyl Phosphites with α-Halo Carbonyl Compounds. Elucidation of the Mechanism of the Perkow Reaction and Related Reactions with Confirmed Experiments

The reactions of silyl phosphites, i.e., tris(trimethylsilyl)phosphite (1), diethyl trimethylsilyl phosphite (11), and bis(trimethylsilyl) ethyl phosphite (12), with a variety of α-halo carbonyl compounds gave the 1:1 carbonyl addition products (6, 13, and 14), enol phosphates (5 and 26), and/or 2-oxophosphonates (4 and 25).Substituents on the phosphites and the α-halo carbonyl compounds have influenced the product ratios.The results of these reactions strongly suggest that the Perkow reaction proceeds via an initial attack of phosphite on the carbonyl carbon of the α-halo carbonyl compound.Treatment of bis(trimethylsilyl) 1--2-halo phosphonates (6) with sodium methoxide in methanol followed by retrimethylsilylation gave bis(trimethylsilyl) 1,2-epoxy phosphonates (17), bis(trimethylsilyl) 2-oxo phosphonates (4), and bis(trimethylsilyl) methyl phosphate (21).On the other hand, diethyl 1-hydroxy-2-halo phosphonates (22) were converted by treatment with different bases to 1,2-epoxy phosphonates (23) predominantly in good yields.When some of tri-n-butyltin alkoxides were used as bases, enol phosphates (26) were obtained selectively.Several bis(trimethylsilyl) esters obtained in the above reactions were successfully converted to the corresponding monoanilinium salts in high yields by treatment with aniline-containing alcohols.