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447714

Sigma-Aldrich

Methylenebis(phosphonic dichloride)

97%

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About This Item

Formule linéaire :
CH2[P(O)Cl2]2
Numéro CAS:
1499-29-2
Poids moléculaire :
249.78
Numéro MDL:
MFCD00013901
Code UNSPSC :
12352100
ID de substance PubChem :
24868355
Nomenclature NACRES :
NA.22

Pureté

97%

Forme

solid

Pf

102-104 °C (lit.)

Chaîne SMILES 

ClP(Cl)(=O)CP(Cl)(Cl)=O

InChI

1S/CH2Cl4O2P2/c2-8(3,6)1-9(4,5)7/h1H2

Clé InChI

VRXYCDTWIOCJBH-UHFFFAOYSA-N

Catégories apparentées

Description générale

Methylenebis(phosphonic dichloride) is an organophosphorus compound that is commonly used in phosphonylation reactions. It is more reactive and the rate of reaction is faster compared to POCl3. This is because the phosphorus center is more electrophilic due to the lack of electron back-donation from the CH2 group.

Application

Methylenebis(phosphonic dichloride) may be used for the following studies:
  • Synthesis of mycophenolic methylenebis(phosphonate) derivatives.
  • Phosphonylation of nucleosides.
  • Preparation of P,P′-partial esters of methylenebisphosphonic acid.
  • Synthesis of symmetrical di- and tetra- esters of methylenebisphosphonic acid.

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H314

Classification des risques

Eye Dam. 1 - Skin Corr. 1B

Risques supp

EUH014

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Consulter la Bibliothèque de documents

Krzysztof W Pankiewicz et al.
Journal of medicinal chemistry, 45(3), 703-712 (2002-01-25)
Novel mycophenolic adenine dinucleotide (MAD) analogues have been prepared as potential inhibitors of inosine monophosphate dehydrogenase (IMPDH). MAD analogues resemble nicotinamide adenine dinucleotide binding at the cofactor binding domain of IMPDH; however, they cannot participate in hydride transfer and therefore
Gantla Vidyasagar Reddy et al.
Synthetic communications, 34(2), 331-344 (2004-01-01)
The preparation of partial esters of methylenebisphosphonic acids has been of recent interest due to their potential therapeutic applications. This paper describes a convenient method to prepare symmetrical methylenebis(alkyl hydrogen phosphonates) by the selective cleavage of the corresponding methylenebis(dialkyl phosphonate)
Aviran Amir et al.
The Journal of organic chemistry, 78(2), 270-277 (2012-12-05)
A new transformation of methylene-bis(phosphonic dichloride) into tetrathiobisphosphonate derivatives is reported. The reaction of methylene-bis(phosphonic dichloride) with 1,2-ethanedithiol in bromoform in the presence of AlCl(3) formed methylene-bis(1,3,2-dithiaphospholane-2-sulfide), which gave rise to O,O'-diester-methylenediphosphonotetrathioate analogues 1a-k upon reaction with phenols and alkyl
Sanjay Bhattarai et al.
Journal of medicinal chemistry, 63(6), 2941-2957 (2020-02-12)
CD73 inhibitors are promising drugs for the (immuno)therapy of cancer. Here, we present the synthesis, structure-activity relationships, and cocrystal structures of novel derivatives of the competitive CD73 inhibitor α,β-methylene-ADP (AOPCP) substituted in the 2-position. Small polar or lipophilic residues increased
A direct method for the synthesis of nucleoside 5'-methylenebis (phosphonate) s from nucleosides.
Kalek M, et al.
Tetrahedron Letters, 46(!4), 2417-2421 (2005)
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