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683-08-9 - Diethyl methylphosphonate, 97% - Diethyl methanephosphonate - Methylphosphonic acid diethyl ester - A14772 - Alfa Aesar

A14772 Diethyl methylphosphonate, 97%

CAS Number
683-08-9
Synonyms
Diethyl methanephosphonate
Methylphosphonic acid diethyl ester

Size Price ($) Quantity Availability
10g 91.05
25g 188.49
50g 339.80
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Diethyl methylphosphonate, 97%

MDL
MFCD00009813
EINECS
211-667-4

Chemical Properties

Formula
C5H13O3P
Formula Weight
152.13
Boiling Point
194°
Flash Point
75°(167°F)
Density
1.040
Refractive Index
1.4140
Solubility
Miscible with water.

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.

Notes

Incompatible with strong oxidizing agents and strong bases.

Literature References

For synthetic applications of the lithio-derivatives of esters of methanephosphonic acid, see Dimethyl­ methyl­phosphonate, 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335-H227

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Combustible liquid.

Precautionary Statements: P210-P261-P280-P305+P351+P338-P304+P340-P362-P312-P405-P403+P233-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1753416
Harmonized Tariff Code
2931.90
TSCA
No
RTECS
SZ9085000

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