CAS 1660-94-2 Tetraethyl methylenediphosphonate (HCID 15455)

Substructure search Find similar structures

Basic information

CAS: 1660-94-2
Standard SMILES: CCOP(=O)(CP(=O)(OCC)OCC)OCC
InChIKey: STJWVOQLJPNAQL-UHFFFAOYSA-N
Molecular formula: C9H22O6P2
Average molar mass: 288.21 g/mol
Monoisotopic mass: 288.08916168

Names & identifiers

Preferred name: Tetraethyl methylenediphosphonate
IUPAC: 1-[diethoxyphosphorylmethyl(ethoxy)phosphoryl]oxyethane
English name: Tetraethyl methylenediphosphonate
Molecular formula: C9H22O6P2
Molecular weight: 288.21

Names & synonyms

Tetraethyl methylenediphosphonate1660-94-2Tetraethyl methylenebisphosphonateEINECS 216-764-5BRN 1813241Phosphonic acid, P,P'-methylenebis-, P,P,P',P'-tetraethyl esterMethylenediphosphonic acid, tetraethyl ester4-01-00-03071 (Beilstein Handbook Reference)RefChem:188555Phosphonic acid, methylenedi, tetraethyl esterPhosphonic acid, methylenebis, tetraethyl esterPhosphonic acid, P,P'methylenebis, P,P,P',P'tetraethyl ester

Show more names

1-5kgNSC 133889AURORA KA-1506enediphosphonateTenofovir Impurity 183BIS(DIETHOXYPHOSPHINYL)METHANEtetraethyl methylenediphosphateTetraethylemethylenediphosphonate

216-764-5STJWVOQLJPNAQL-UHFFFAOYSA-Ntetraethyl methylenebis(phosphonate)1-[diethoxyphosphorylmethyl(ethoxy)phosphoryl]oxyethaneTetraethyl methanediphosphonateMethylenebis(diethylphosphonate)Phosphonic acid, methylenebis-, tetraethyl esterTetraethyl diphosphonomethane

Properties

Computed structural properties

XLogP: 0.3
Topological polar surface area: 71.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 6
Rotatable bonds: 10
Heavy atoms: 17
Formal charge: 0
Complexity: 245

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organophosphates, Other

SpringerMaterials PropertiesViscosity

Physical DescriptionClear colorless liquid; [Sigma-Aldrich MSDS]

Physicochemical properties

Boiling point: 171 · 171-174 °C11 mm Hg(lit.)
Density: 1.16 g/mL · 1.16 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.442(lit.)
Flash point: 230 °F · >230 °F
storage temp.: Inert atmosphere,Room Temperature
solubility: Chloroform (Sparingly), Methanol (Slightly)
form: Liquid
Specific Gravity: 1.16 · 1.160
color: Clear yellow to yellow-brown
Water Solubility

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryIntravenous LD50 (mouse) = 180 mg/kg; [RTECS] A skin and strong eye irritant; [Sigma-Aldrich MSDS] See Dimethyl methylphosphonate, Dibutyl butylphosphonate, and Diethyl ethylphosphonate.

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
rtecs: SZ9150000
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,
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,C
hazard_note: Corrosive
safety_code: 26-36
Storage Class: 10 - Combustible liquids

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationPhosphonic acid, P,P'-methylenebis-, P,P,P',P'-tetraethyl ester: INACTIVE

Applications · 2 items

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 synthaseUnnatural alpha-amino acid derivatives containing gem-biphosphonatesBiphenyl sulfonylamino Me bisphosphonic acids as inhibitors of matrix metalloproteinases and bone resorptionLycopene via Wittig-Horner reactionAlkylaminoethylbisphosphinic acids to target farnesyl diphosphate synthaseAromatic bisphosphonates for use as inhibitors of geranylgeranyl diphosphate synthasePrecursor for synthesis of dendritic polyglycerol anions used toward L-selectin inhibition