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158216

Sigma-Aldrich

Methyl dichlorophosphate

85%

Synonym(s):

Methyl phosphorodichloridate

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About This Item

Linear Formula:
Cl2P(O)OCH3
CAS Number:
677-24-7
Molecular Weight:
148.91
EC Number:
211-639-1
MDL number:
MFCD00002068
UNSPSC Code:
12352100
PubChem Substance ID:
24849724
NACRES:
NA.22
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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[1]
  • 8-(2′′-hydroxyethoxy)adenosine-5′,2′′-phosphate derivative[2]
  • analogs of (R)-1-O-hexadecyl-2-palmitoyl-sn-glycero-3-phosphoethanolamine poly(ethylene glycol)[3]
  • dioxaphosphorino[m,n-x]pyridines compounds[4]

Analysis Note

may contain methyl alcohol as impurity

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW1849
MKCK4768
MKCB1610V
MKBG6668V
02724AJ

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Syntheses of Ortho-Hydroxymethylpyridinols and Dioxaphosphorino [m, nx] pyridines.
Leroy F, et al.
Synthetic Communications, 26(12), 2257-2272 (1996)
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
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
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).

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