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METHYLENEBIS(PHOSPHONIC DICHLORIDE)

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Products Intro: Product Name:METHYLENEBIS(PHOSPHONIC DICHLORIDE)
CAS:1499-29-2
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Products Intro: Product Name:METHYLENEBIS(PHOSPHONIC DICHLORIDE)
CAS:1499-29-2
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CAS:1499-29-2
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METHYLENEBIS(PHOSPHONIC DICHLORIDE) manufacturers

METHYLENEBIS(PHOSPHONIC DICHLORIDE) Basic information
Product Name:METHYLENEBIS(PHOSPHONIC DICHLORIDE)
Synonyms:METHYLENEDIPHOSPHONIC DICHLORIDE;METHYLENEBIS(PHOSPHONIC DICHLORIDE);BIS(DICHLOROPHOSPHONYL)METHANE;Bis-(dichlorophosphinyl)-methane;Phosphonic dichloride, P,P'-methylenebis-;bis(dichlorophosphoryl)methane;Methylenedisphosphonic Dichloride
CAS:1499-29-2
MF:CH2Cl4O2P2
MW:249.78
EINECS:
Product Categories:Building Blocks;Chemical Synthesis;Organic Building Blocks;Phosphorus Compounds;Phosphorus Halides;Organic Building Blocks;Phosphorus Compounds;Phosphorus Halides
Mol File:1499-29-2.mol
METHYLENEBIS(PHOSPHONIC DICHLORIDE) Structure
METHYLENEBIS(PHOSPHONIC DICHLORIDE) Chemical Properties
Melting point 102-104 °C(lit.)
Boiling point 329.0±25.0 °C(Predicted)
density 1.798±0.06 g/cm3(Predicted)
solubility Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate (Sparingly), Methanol (Slightly)
form crystalline powder
color Faint beige
Stability:Moisture Sensitive
Safety Information
Hazard Codes C
Risk Statements 14-34
Safety Statements 26-27-36/37/39-45
RIDADR UN 3261 8/PG 1
WGK Germany 3
HS Code 2931599090
MSDS Information
ProviderLanguage
SigmaAldrich English
METHYLENEBIS(PHOSPHONIC DICHLORIDE) Usage And Synthesis
DescriptionMethylenebis (phosphonic dichloride) is an organophosphorus compound commonly used in phosphonation reactions. It is more reactive and faster than POCl. This is due to the fact that the phosphorus centre is more electrophilic due to the lack of electron feedback from the CH2 group.
Chemical PropertiesCrystals of the Methylenebis(phosphonic dichloride) are monoclinic, space group C2/c, with a= 15·866(5), b= 5·845(1), c= 9·161 (3)A, β= 106·59(2)°, Z= 4. The molecules, which display a crystallographically imposed C2 symmetry, are linked together through two C–H ? O(P) hydrogen bonds, of length 3·23(1)A, into infinite chains in the z direction. Rigid-body analysis reveals that pronounced rotational and translational motions are associated with the axis of minimum inertia and least cross-section. Bond lengths (corrected for libration) are: P–Cl 1·994(2) and 1·997 (2), PO 1·463(4), P–C 1·804(4)A; angle P–C–P 116·4(4)°, the structure was solved by direct methods and refined by full-matrix least-squares to R 0·041 for 641 diffractometer-measured unique reflections[1].
UsesMethylenebis(phosphonic Dichloride) is used as a reagent in synthesis of several organic compounds including that of nucleoside 5'-methylenebis(phosphonate)s and bisphosphonated glycopeptide prodrugs for the treatment of osteomyelitis.
ApplicationMethylenebis (phosphonic dichloride) can be used for the following studies:
(1) Synthesis of mycophenolic methylenebis(phosphonate) derivatives.
(2) Phosphonylation of nucleosides.
(3) Preparation of P,P′-partial esters of methylenebisphosphonic acid.
(4) Synthesis of symmetrical di- and tetra- esters of methylenebisphosphonic acid.
References[1] SHELDRICK W. Crystal structure of methylenebis(phosphonic dichloride)[J]. Journal of The Chemical Society-dalton Transactions, 1975. DOI:10.1039/DT9750000943.
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