Diethyl methylphosphonate, 97%, Thermo Scientific Chemicals

Name: Diethyl methylphosphonate, 97%, Thermo Scientific Chemicals
SKU: A14772.14

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Catalog number A14772.14

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25 g

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Chemical Identifiers

CAS683-08-9

IUPAC Namediethyl methylphosphonate

Molecular FormulaC5H13O3P

InChI KeyNYYLZXREFNYPKB-UHFFFAOYSA-N

SMILESCCOP(C)(=O)OCC

Specifications

Specification Sheet

Appearance (Color)Clear colorless

FormLiquid

Assay (GC)≥96.0%

Refractive Index1.4115-1.4165 @ 20?C

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
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.

Solubility
Miscible with water.

Notes
Incompatible with strong oxidizing agents and strong bases.

RUO – Research Use Only

General References:

For synthetic applications of the lithio-derivatives of esters of methanephosphonic acid, see Dimethyl methyl phosphonate, A14268.
Dialkylation has been used in the synthesis of cyclobutanephosphonates which are intermediates in the synthesis of 3-phosphonocyclobutyl amino acids: J. Chem. Soc., Perkin 1, 493 (1997).
Reaction of the lithio-derivative with dialkyl cyanamides gives, instead of the expected 2-phosphorylacetamide, a rearranged N-phosphorylated amidine: Chem. Commun., 609 (1998):
Mattea, F.; Peters, C. J.; Kroon, M. C. Experimental Determination of the Solubilities of CO₂ and CH₄ in Diethyl Methylphosphonate. J. Chem. Eng. Data 2011, 56 (6), 2960-2963.
JeongaJang, Y.; Murale, D. P.; Churchill, D. G. Novel reversible and selective nerve agent simulant detection in conjunction with superoxide turn-on probing. Analyst 2014, 139 (7), 1614-1617.