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Merck
CN

64256

Tetraethyl methylenediphosphonate

purum, ≥97.0% (GC)

Synonym(s):

Bis(diethoxyphosphinyl)methane, Methylenediphosphonic acid tetraethylester, NSC 133889

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About This Item

Linear Formula:
CH2[P(O)(OCH2CH3)2]2
CAS Number:
1660-94-2
Molecular Weight:
288.21
EC Number:
216-764-5
UNSPSC Code:
12352108
PubChem Substance ID:
329759942
Beilstein/REAXYS Number:
1813241
MDL number:
MFCD00039887

Key Documents

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InChI key

STJWVOQLJPNAQL-UHFFFAOYSA-N

InChI

1S/C9H22O6P2/c1-5-12-16(10,13-6-2)9-17(11,14-7-3)15-8-4/h5-9H2,1-4H3

SMILES string

CCOP(=O)(CP(=O)(OCC)OCC)OCC

grade

purum

assay

≥97.0% (GC)

reaction suitability

reaction type: C-C Bond Formation

bp

171-174 °C/11 mmHg (lit.)

density

1.16 g/mL at 25 °C (lit.)

Application

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

Other Notes

Horner-Wittig reagent for the synthesis of vinylic phosphonates ; Preparation of isosters of phosphates by Horner- Wittig reaction followed by hydrogenation

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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N. Lalinde et al.
Tetrahedron, 39, 2369-2369 (1983)
H.P. Albrecht et al.
Tetrahedron, 40, 79-79 (1984)
W.S. Wadsworth
Org. React., 25, 73-73 (1977)

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