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Sigma-Aldrich

Methyl dichlorophosphate

85%

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Synonym(s):
Methyl phosphorodichloridate
Linear Formula:
Cl2P(O)OCH3
CAS Number:
Molecular Weight:
148.91
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

85%

refractive index

n20/D 1.436 (lit.)

bp

62-64 °C/15 mmHg (lit.)

density

1.488 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COP(Cl)(Cl)=O

InChI

1S/CH3Cl2O2P/c1-5-6(2,3)4/h1H3

InChI key

SNVCRNWSNUUGEA-UHFFFAOYSA-N

Application

Methyl dichlorophosphate was used in the synthesis of:
  • 4,6-cyclic phosphate tetrasaccharide
  • 8-(2′′-hydroxyethoxy)adenosine-5′,2′′-phosphate derivative
  • analogs of (R)-1-O-hexadecyl-2-palmitoyl-sn-glycero-3-phosphoethanolamine poly(ethylene glycol)
  • dioxaphosphorino[m,n-x]pyridines compounds

Analysis Note

may contain methyl alcohol as impurity

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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T Maruyama et al.
Nucleic acids symposium series, (17)(17), 61-63 (1986-01-01)
Reaction of 8-bromo-2',3'-O-isopropylidene-5'-O-(tetrahydropyran-2-yl) adenosine (Ib) with lithium 2-(tetrahydropyran-2-yloxy) ethoxide, followed by removal of the tetrahydropyran-2-yl groups, afforded 8-(2''-hydroxyethoxy)-2',3'-O-isopropylideneadenosine (II). Successive treatment of II with n-butyllithium and with methyl dichlorophosphate provided the 5',2''-(methyl phosphate) derivative (IIIa and IIIb).
Dominika Turek et al.
Organic & biomolecular chemistry, 4(7), 1236-1241 (2006-03-25)
A spacer-equipped tetrasaccharide, p-aminocyclohexylethyl alpha-l-Colp-(1-->2)-beta-d-Galp-(1-->3)-[alpha-l-Colp-(1-->4)]-beta-D-GlcpNAc, containing a 4,6-cyclic phosphate in the galactose residue, has been synthesised. The structure corresponds to a part of the repeating unit of the capsular (and lipo-) polysaccharide of the endemic bacteria Vibrio cholerae type O139
Syntheses of Ortho-Hydroxymethylpyridinols and Dioxaphosphorino [m, nx] pyridines.
Leroy F, et al.
Synthetic Communications, 26(12), 2257-2272 (1996)
Thomas L Andresen et al.
Journal of medicinal chemistry, 47(7), 1694-1703 (2004-03-19)
An enzymatically activated liposome-based drug-delivery concept involving masked antitumor ether lipids (AELs) has been investigated. This concept takes advantage of the cytotoxic properties of AEL drugs as well as the membrane permeability enhancing properties of these molecules, which can lead

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