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447714

Sigma-Aldrich

Methylenebis(phosphonic dichloride)

97%

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About This Item

Formula condensata:
CH2[P(O)Cl2]2
Numero CAS:
1499-29-2
Peso molecolare:
249.78
Numero MDL:
MFCD00013901
Codice UNSPSC:
12352100
ID PubChem:
24868355
NACRES:
NA.22

Saggio

97%

Forma fisica

solid

Punto di fusione

102-104 °C (lit.)

Stringa SMILE

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

InChI

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

Categorie correlate

Descrizione generale

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.

Applicazioni

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.

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H314

Classi di pericolo

Eye Dam. 1 - Skin Corr. 1B

Rischi supp

EUH014

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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Methylenediphosphonic acid for molecular studies & mass spectrometry

Sigma-Aldrich

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Trimethyl phosphate 97%

Sigma-Aldrich

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Trimethyl phosphate

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
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
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
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