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About This Item
Linear Formula:
CH2[P(O)Cl2]2
CAS Number:
Molecular Weight:
249.78
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
Related Categories
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Supplementary Hazards
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
Facile high yielding synthesis of symmetric esters of methylenebisphosphonic acid.
Stepinski DC, et al.
Tetrahedron, 57(41), 8637-8645 (2001)
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)
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
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