TETRAETHYL METHYLENEDIPHOSPHONATE

TETRAETHYL METHYLENEDIPHOSPHONATE Basic information
Product Name:TETRAETHYL METHYLENEDIPHOSPHONATE
Synonyms:methylenedi-phosphonicacitetraethylester;METHYLENEDIPHOSPHONIC ACID TETRAETHYL ESTER;AURORA KA-1506;BIS(DIETHOXYPHOSPHINYL)METHANE;TETRAETHYL(METHYLENE)BISPHOSPHONATE;TETRAETHYL METHYLENEDIPHOSPHONATE;Tetraethyl methylenediphosphonate, 98+%;methanediyl-bis-phosphonic acid tetraethyl ester
CAS:1660-94-2
MF:C9H22O6P2
MW:288.21
EINECS:216-764-5
Product Categories:Naphthyridine,Quinoline
Mol File:1660-94-2.mol
TETRAETHYL METHYLENEDIPHOSPHONATE Structure
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.)
Fp >230 °F
storage temp. Inert atmosphere,Room Temperature
solubility Chloroform (Sparingly), Methanol (Slightly)
form Liquid
color Clear yellow to yellow-brown
Specific Gravity1.160
Water Solubility Slightly miscible with water.
BRN 1813241
InChIKeySTJWVOQLJPNAQL-UHFFFAOYSA-N
CAS DataBase Reference1660-94-2(CAS DataBase Reference)
EPA Substance Registry SystemPhosphonic 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
Toxicitymouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03139,
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
TETRAETHYL METHYLENEDIPHOSPHONATE Usage And Synthesis
Chemical Propertiesclear yellow to yellow-brown liquid
UsesTetraethyl 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.
UsesReactant 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
TETRAETHYL METHYLENEDIPHOSPHONATE Preparation Products And Raw materials
Preparation ProductsDIETHYL VINYLPHOSPHONATE-->METHYLENEBIS(PHOSPHONIC DICHLORIDE)-->DIETHYL IODOMETHYLPHOSPHONATE-->METHYLENEDIPHOSPHONIC ACID
Tetraethyl(ethoxycarbonylethylidene)bisphosphonate TETRAISOPROPYL VINYLIDENE DIPHOSPHONATE TETRAISOPROPYL DICHLOROMETHYLENE DIPHOSPHONATE Tetraethyl-(N-benzylideneaminomethylene)bisphosphonate, stabilized, min. 95 % TETRAETHYL(3-AMINOPROPYLIDENE)BISPHOSPHONATE TETRAETHYL(4-AMINOBUTYLIDENE)BISPHOSPHONATE apomine AURORA KA-1507 TETRAETHYL(4-HYDROXYBUTYLIDENE)BISPHOSPHONATE TETRAETHYL(CARBOXYETHYLIDENE)BISPHOSPHONATE BIS[(4-CHLOROPHENYL)THIOMETHYLENE]BIPHOSPHONIC ACID, TETRAISOPROPYL ESTER TETRAETHYL DIMETHYLAMINOMETHYLENEDIPHOSPHONATE Tetraethylfluoromethylene-diphosphonate TETRAETHYL(TROC-AMINOMETHYLENE)BISPHOSPHONATE TETRAETHYL METHYLENEDIPHOSPHONATE SR 12813 TETRAETHYL(AMINOMETHYLENE)BISPHOSPHONATE OXALATE SALT TETRAETHYL(3-HYDROXYPROPYLIDENE)BISPHOSPHONATE

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