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1660-94-2 - Tetraethyl methylenediphosphonate, 98+% - Methylenediphosphonic acid tetraethyl ester - A14532 - Alfa Aesar

A14532 Tetraethyl methylenediphosphonate, 98+%

CAS Number
1660-94-2
Synonyms
Methylenediphosphonic acid tetraethyl ester

Size Price ($) Quantity Availability
5g 63.76
25g 255.44
100g 672.00
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Tetraethyl methylenediphosphonate, 98+%

MDL
MFCD00039887
EINECS
216-764-5

Chemical Properties

Formula
C9H22O6P2
Formula Weight
288.22
Boiling Point
151-153°/1.2mm
Flash Point
>110°(230°F)
Density
1.162
Refractive Index
1.4400
Solubility
Slightly miscible with water.

Applications

Tetraethyl methylidenediphosphonate is used in the synthesis of tetrazoloquinoline-based mono- and bisphosphonate esters. It acts as an intermediate for the synthesis of bisphosphonate and bisphosphonic acid derivatives with anticancer and antischistosomal activity. It is also used as a reactant for synthesis of dual substrate-site inhibitors of 3-deoxy-D-arabino-heputosonate 7-phosphate synthase and alpha-amino acid derivatives containing gem-biophosphonates, Lycopene through Wittig-Horner reaction. It is also used as a precursor for the preparation of dendritic polyglycerol anions.

Notes

Incompatible with strong oxidizing agents.

Literature References

Reacts with aromatic aldehydes to give styrylphosphonates in a two-phase system, no added phase-transfer catalyst being necessary: Synthesis, 396 (1976). For cleavage of the resulting vinyl phosphonates to ɑ-hydroxyaldehydes, see Osmium(VIII)­ oxide, 12103.

Pachl, P.; Simak, O.; Rezacova, P.; Fabry, M.; Budesínsky, M.; Rosenberg, I.; Brynda, J. Structure-based design of a bisphosphonate 5'(3')-deoxyribonucleotidase inhibitor. Med. Chem. Commun. 2015, 6 (9), 1635-1638.

Faísca Phillips, A. M.; Barros, M. T. Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction. Eur. J. Org. Chem. 2014, 2014 (1), 152-163.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319

Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P280g-P305+P351+P338

Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Other References

Beilstein
1813241
Harmonized Tariff Code
2931.90
TSCA
Yes
RTECS
SZ9150000

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