TETRAETHYL METHYLENEDIPHOSPHONATE Chemical Properties

Boiling point:

171-174 °C11 mm Hg(lit.)

Density 

1.16 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.442(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Liquid

Specific Gravity

1.160

color 

Clear yellow to yellow-brown

Water Solubility 

Slightly miscible with water.

BRN 

1813241

InChIKey

STJWVOQLJPNAQL-UHFFFAOYSA-N

CAS DataBase Reference

1660-94-2(CAS DataBase Reference)

EPA Substance Registry System

Phosphonic acid, methylenebis-, tetraethyl ester (1660-94-2)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

SZ9150000

Hazard Note 

Corrosive

TSCA 

Yes

HS Code 

29319090

Toxicity

mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03139,

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

TETRAETHYL METHYLENEDIPHOSPHONATE Usage And Synthesis

Chemical Properties

clear yellow to yellow-brown liquid

Uses

Tetraethyl methylidenebisphosphonate, can be used in the synthesis of tetrazoloquinoline-based mono- and bisphosphonate esters as potent anti-inflammatory agents. It is also an intermediate for the synthesis of new bisphosphonate and bisphosphonic acid derivatives with anticancer and antischistosomal activity.

Uses

Reactant for synthesis of:

• Dual substrate-site inhibitors of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase
• Unnatural alpha-amino acid derivatives containing gem-biphosphonates
• Biphenyl sulfonylamino Me bisphosphonic acids as inhibitors of matrix metalloproteinases and bone resorption
• Lycopene via Wittig-Horner reaction
• Alkylaminoethylbisphosphinic acids to target farnesyl diphosphate synthase
• Aromatic bisphosphonates for use as inhibitors of geranylgeranyl diphosphate synthase

Precursor for synthesis of dendritic polyglycerol anions used toward L-selectin inhibition

Synthesis Reference(s)

Synthetic Communications, 20, p. 1865, 1990 DOI: 10.1080/00397919008053112
Tetrahedron Letters, 34, p. 1515, 1993 DOI: 10.1016/S0040-4039(00)60333-7

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