Diethyl (2-oxopropyl)phosphonate

Base Information

• Chemical Name: Diethyl (2-oxopropyl)phosphonate
• CAS No.: 1067-71-6
• Molecular Formula: C7H15O4P
• Molecular Weight: 194.167
• Hs Code.: 29319090
• European Community (EC) Number: 682-094-9
• NSC Number: 408852
• DSSTox Substance ID: DTXSID90147731
• Nikkaji Number: J584.455J
• Wikidata: Q72462074
• Mol file: 1067-71-6.mol

Synonyms:Diethyl (2-oxopropyl)phosphonate;1067-71-6;1-diethoxyphosphorylpropan-2-one;Diethyl(2-oxopropyl)phosphonate;DIETHYL ACETONYLPHOSPHONATE;diethyl 2-oxopropylphosphonate;(2-Oxopropyl)phosphonic Acid Diethyl Ester;Phosphonic acid, (2-oxopropyl)-, diethyl ester;Acetonylphosphonic Acid Diethyl Ester;MFCD00044728;(2-oxo-propyl)-phosphonic acid diethyl ester;NSC408852;Diethyl acetylmethylphosphonate;SCHEMBL246813;1-Diethoxyphosphinyl-2-propanone;DTXSID90147731;1-diethoxyphosphoryl-propan-2-one;RSAFKRSMGOSHRK-UHFFFAOYSA-N;AMY19196;STR04005;BBL100721;STL554515;AKOS005255526;CS-W008714;NSC 408852;NSC-408852;PB48769;2-Oxopropylphosphonic acid diethyl ester;Diethyl (2-oxopropyl)phosphonate, 96%;SY015737;BB 0263080;D3174;FT-0633273;EN300-86234;J-001645

Chemical Property of Diethyl (2-oxopropyl)phosphonate

Chemical Property:

• Appearance/Colour: CLEAR COLORLESS TO LIGHT YELLOW LIQUID
• Vapor Pressure: 0.0105mmHg at 25°C
• Refractive Index: n20/D 1.433(lit.)
• Boiling Point: 263.1 °C at 760 mmHg
• Flash Point: 126.9 °C
• PSA: 62.41000
• Density: 1.09 g/cm³
• LogP: 1.84150
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Miscible with tetrahydrofuran, ether, dichloromethane and chloro
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 194.07079595
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

99% ^*data from raw suppliers

Diethyl (2-oxopropyl)phosphonate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CC(=O)C)OCC
• Uses: Diethyl (2-Oxopropyl)phosphonate, is used in the preparation of enantipure acetoxyalkanephosphonates thru dynamic enzymic kinetic resolution alpha- and beta-hydroxalkanephosphonates.

Technology Process of Diethyl (2-oxopropyl)phosphonate

There total 89 articles about Diethyl (2-oxopropyl)phosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

phosphonic acid diethyl ester (762-04-9) + 1-bromoacetone (598-31-2) → Diethyl (2-oxopropyl)phosphonate (1067-71-6)

Guidance literature:

With C₃₀H₃₆B₁₀CuO₄P₂; potassium carbonate; at 20 ℃; for 7h; Time; Reagent/catalyst;

Reference yield: 91.0%

diethyl (2-hydroxy-4-oxopent-2-en-3-yl)phosphonate → Diethyl (2-oxopropyl)phosphonate (1067-71-6)

Guidance literature:

With dipotassium peroxodisulfate; silver(I) acetate; In water; N,N-dimethyl-formamide; at 85 ℃; for 24h; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201704910

Reference yield: 88.0%

diethyl (2-methylallyl)phosphonate (51533-70-1) → Diethyl (2-oxopropyl)phosphonate (1067-71-6)

Guidance literature:

With dimethylsulfide; ozone; In dichloromethane;

DOI:10.1080/00397919808004906

upstream raw materials:

sodium diethyl phosphite

chloroacetone

diethyl ether

phosphonic acid diethyl ester

Downstream raw materials:

(2-amino-4-methyl-thiazol-5-yl)-phosphonic acid diethyl ester

(3E,5E)-6-(2-Nitro-phenyl)-hexa-3,5-dien-2-one

1-(2-phenylcyclopropyl)ethanone

Diethyl-1-(3-methyl-2-butenyl)-2-oxopropanphosphonat

Refernces

• 1、 Tomicka et al.. "-". . p. 5739. Retrieved 1968.
• 2、 Lengkeek, Nigel A.,Greenwood, Paul F.,Nguyen, Blake,Koutsantonis, George A.,Piggott, Matthew J.. "Making mixtures to solve structures: structural elucidation via combinatorial synthesis". . p. 141 - 150. Retrieved 2010.
• 3、 Kosobokov, Mikhail D.,Titanyuk, Igor D.,Beletskaya, Irina P.. "An expedient synthesis of diethyl diazomethylphosphonate". . p. 142 - 143. Retrieved 2011.
• 4、 Sasaki. "". . p. 2703. Retrieved 1966.
• 5、 Kitamura,Tokunaga,Noyori. "Asymmetric hydrogenation of β-keto phosphonates: A practical way to fosfomycin". . p. 2931 - 2932. Retrieved 1995.
• 6、 Gil, Jun Mo,Park, Kwang Young,Hah, Jung Hwan,Oh, Dong Young. "A new and facile synthetic route to 1-alkyl-2-oxopropylphosphonates: 1 alkylation with subsequent ozonolysis of 2-methyl allylic phosphonates". . p. 3601 - 3607. Retrieved 1998.
• 7、 Chanthamath, Soda,Ozaki, Seiya,Shibatomi, Kazutaka,Iwasa, Seiji. "Highly stereoselective synthesis of cyclopropylphosphonates catalyzed by chiral Ru(II)-pheox complex". . p. 3012 - 3015. Retrieved 2014.
• 8、 Liu,Murakami,Seki,He,Yeung,Kuzuyama,Seto,Liu. "Protein purification and function assignment of the epoxidase catalyzing the formation of fosfomycin [10]". . p. 4619 - 4620. Retrieved 2001.
• 9、 Balczewski, Piotr. "Novel 1-phosphonyl radicals derived from 1-mono and 1,1-di-heterosubstituted 2-oxoalkylphosphonates as useful phosphotoorganic intermediates in organic synthesis". . p. 2199 - 2212. Retrieved 1997.
• 10、 Amarnath, Venkataraman,Amarnath, Kalyani,Masterson, Tina,Davies, Sean,Roberts II, Jackson. "A simplified synthesis of the diastereomers of Levuglandin E2". . p. 397 - 408. Retrieved 2005.