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447714

Methylenebis(phosphonic dichloride)

97%

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About This Item

Linear Formula:
CH2[P(O)Cl2]2
CAS Number:
1499-29-2
Molecular Weight:
249.78
NACRES:
NA.22
PubChem Substance ID:
24868355
UNSPSC Code:
12352100
MDL number:
MFCD00013901
Assay:
97%
Form:
solid
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Quality Level

200

assay

97%

form

solid

mp

102-104 °C (lit.)

functional group

phosphine oxide

SMILES string

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

InChI

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

InChI key

VRXYCDTWIOCJBH-UHFFFAOYSA-N

General description

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.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK5171
MKCF9997
MKCD1769
MKBS4017V
MKBG1558V

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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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Global Trade Item Number

SKUGTIN
447714-5G04061832288680