Diethyl methylphosphonate

Base Information

• Chemical Name: Diethyl methylphosphonate
• CAS No.: 683-08-9
• Molecular Formula: C5H13O3P
• Molecular Weight: 152.13
• Hs Code.: 29310095
• European Community (EC) Number: 211-667-4
• UNII: JRX9AX7374
• DSSTox Substance ID: DTXSID80218449
• Nikkaji Number: J43.477I
• Wikidata: Q26840949
• Mol file: 683-08-9.mol

Synonyms:DEMP;diethyl methanephosphonate;diethyl methylphosphonate

Chemical Property of Diethyl methylphosphonate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.00119mmHg at 25°C
• Refractive Index: n20/D 1.414(lit.)
• Boiling Point: 194 °C at 760 mmHg
• Flash Point: 75.6 °C
• PSA: 45.34000
• Density: 1.028 g/cm³
• LogP: 1.88230
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Miscible with water.
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 152.06023127
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

98% ^*data from raw suppliers

Diethyl methylphosphonate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOP(=O)(C)OCC
• Uses: Diethyl methylphosphonate is used as a precursor for the synthesis of gem-difluroalkenyphosphonate via reaction with alpha-trifluromethylstyrene. It is also used in the synthesis of phosphonylated peptides, fluoroalkyl alpha- and beta-aminophosphonates, pyridone alkaloids with neuritogenic activity and lipophilic meropenem-derived prodrugs. It is readily mineralized by photoexcited titanium dioxide (TiO2).

Technology Process of Diethyl methylphosphonate

There total 98 articles about Diethyl methylphosphonate 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: 100.0%

diethyl-1-magnesium chloride methanephosphonate (110625-05-3) → Diethyl methylphosphonate (683-08-9)

Guidance literature:

With water; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/0022-328X(86)82070-8

Reference yield: 99.0%

triethyl phosphite (122-52-1) + methyl iodide (74-88-4) → Diethyl methylphosphonate (683-08-9)

Guidance literature:

for 0.05h; Irradiation;

DOI:10.1080/10426509808032465

Reference yield: 97.0%

triethyl phosphite (122-52-1) + methyl iodide (74-88-4) → Diethyl methylphosphonate (683-08-9) + ethyl iodide (75-03-6)

Guidance literature:

at 130 ℃; for 0.0833333h; microwave irradiation;

DOI:10.1002/chem.200600168

upstream raw materials:

sodium diethyl phosphite

dimethyl sulfate

methanol

triethyl phosphite

Downstream raw materials:

(2-Hydroxy-2,2-diphenyl-ethyl)-phosphonic acid diethyl ester

diethyl (2-oxobutyl)phosphonate

diethyl (3,3-dimethyl-2-oxobutyl)phosphonate

oxo-2 phenyl-4 butenyl-3,4 phosphonate de diethyle

Refernces

Highly stereoselective total synthesis of methynolide, the aglycon of the 12-membered macrolide antitiotic methymycin. II. Kinetic acetalization and synthesis of the seco-acid

10.1248/cpb.35.2196

Yuji Oikawa, Tatsuyoshi Tanaka, Tatsuo Hamada, and Osamu Yonemitsu detail a highly stereoselective synthesis of the seco-acid (3) of the aglycone methoxylactone (1) of the 12-membered macrolide antibiotic methicillin. The synthesis started from D-glucose and involved the Wittig-Horner coupling of two fragments (i and ii). Fragment i (4) was synthesized by kinetic acetalization with p-methoxybenzylide (MP) acetal protection, while fragment ii (5) was obtained from the Prelog-Djerassi lactone-type intermediate (2) through a series of reactions including protection, hydrolysis, reduction, and oxidation. Diethyl methylphosphonate, a widely used organic synthesis reagent, was used to synthesize fragment ii (5) to introduce the phosphonate group. The coupling of these fragments formed the ring-opened acid (3), which was confirmed by nuclear magnetic resonance (NMR) and mass spectrometry. This work represents a major advance in the synthesis of complex macrolide antibiotics, demonstrating the utility of noncyclic stereocontrolled approaches and the importance of careful choice of protecting groups to achieve high stereoselectivity.

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