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426431

Sigma-Aldrich

Tetraisopropyl methylenediphosphonate

97%

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About This Item

Linear Formula:
CH2[P(O)[OCH(CH3)2]2]2
CAS Number:
1660-95-3
Molecular Weight:
344.32
Beilstein:
1080180
EC Number:
216-765-0
MDL number:
MFCD00015021
UNSPSC Code:
12352100
PubChem Substance ID:
24866704
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.431 (lit.)

bp

155 °C/0.5 mmHg (lit.)

density

1.08 g/mL at 25 °C (lit.)

SMILES string

CC(C)OP(=O)(CP(=O)(OC(C)C)OC(C)C)OC(C)C

InChI

1S/C13H30O6P2/c1-10(2)16-20(14,17-11(3)4)9-21(15,18-12(5)6)19-13(7)8/h10-13H,9H2,1-8H3

InChI key

ODTQUKVFOLFLIQ-UHFFFAOYSA-N

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General description

Tetraisopropyl methylenediphosphonate (IPCP) is a tetraisopropyl ester of methylenediphosphonic acid. It is an electroneutral ligand, reported to be synthesized from triisopropyl phosphate. Powder electron paramagnetic resonance (EPR) studies of tris complexes of Cu(II) complexes with IPCP has been analyzed.

Application

Tetraisopropyl methylenediphosphonate [T(iPr)MDP] forms a synergistic mixture with hydrogen dicarbollylcobaltate in nitrobenzene which was used in the extraction of europium and americium.
It may be used in the synthesis of the following:
  • tetraisopropyl ethenylidenebisphosphonate.
  • tetraisopropyl 4-acetylthiobutane-1,1-diphosphonate
  • tetraisopropyl 2-(3,5-bis(bromomethyl)phenyl)ethane-1,1-diphosphonate

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

320.0 °F - closed cup

Flash Point(C)

160 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Extraction of europium and americium into nitrobenzene by using synergistic mixture of hydrogen dicarbollylcobaltate and tetraisopropyl methylene diphosphonate.
Makrlik E, et al.
J. Radioanal. Nucl. Chem., 283(3), 727-733 (2010)
Synthesis of novel bisphosphonate polyamine conjugates and their affinity to hydroxyapatite.
Sankala E, et al.
ARKIVOC (Gainesville, FL, United States), 4, 233-241 (2012)
Synthesis of Tetraisopropyl Methyenediphosphonate.
Jian-ming XU.
Jing Xi Hua Gong Zhong Jian Ti / Fine Chemical Intermediates, 4, 007-007 (2002)
Electron paramagnetic resonance studies of some copper (II) complexes with organophosphorus chelates.
Joesten MD, et al.
Journal of the American Chemical Society, 93(5), 1138-1140 (1971)
L Gil et al.
Bioorganic & medicinal chemistry, 7(5), 901-919 (1999-07-10)
Conjugates of bisphosphonates (potential bone resorption inhibitors) and prostaglandin E2 (a bone formation enhancer) were prepared and evaluated for their ability to bind to bone and to liberate, enzymatically, free PGE2. The conjugate 3, an amide at C-1 of PGE2

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