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437891

Sigma-Aldrich

Dimethyl chlorophosphate

96%

Synonym(s):

Dimethyl phosphorochloridate

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About This Item

Linear Formula:
(CH3O)2P(O)Cl
CAS Number:
813-77-4
Molecular Weight:
144.49
MDL number:
MFCD00117904
UNSPSC Code:
12352100
PubChem Substance ID:
24867405
NACRES:
NA.22

Quality Level

100

Assay

96%

form

liquid

refractive index

n20/D 1.413 (lit.)

bp

80 °C/25 mmHg (lit.)

density

1.34 g/mL at 25 °C (lit.)

SMILES string

COP(Cl)(=O)OC

InChI

1S/C2H6ClO3P/c1-5-7(3,4)6-2/h1-2H3

InChI key

NGFFLHMFSINFGB-UHFFFAOYSA-N

Application

Dimethyl chlorophosphate may be used for the preparation of (E)-3-cyanophosphoenolpyruvate, by reaction with the potassium enolate of ethyl cyanopyruvate. It may be used for the synthesis of mono- and diphosphate esters of 2-arachidonyl glyceryl ether.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H314

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic 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
MKCN3761
MKCM6247
MKCL1520
MKCH1753
MKCF9622

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P Wirsching et al.
Biochemistry, 24(26), 7602-7606 (1985-12-17)
(E)-3-Cyanophosphoenolpyruvate has been synthesized by reacting dimethyl chlorophosphate with the potassium enolate of ethyl cyanopyruvate. The resulting trialkyl ester was deesterified with bromotrimethylsilane followed by potassium hydroxide. Subsequent treatment with Dowex-50-H+ resin and cyclohexylamine afforded the tricyclohexylammonium salt; only the
Juha Juntunen et al.
Journal of medicinal chemistry, 46(23), 5083-5086 (2003-10-31)
The poor aqueous solubility of 2-arachidonyl glyceryl ether (noladin ether) 2 hinders both pharmacological studies and pharmaceutical development. The synthesized mono- and diphosphate esters of noladin ether (4 and 6) considerably increased the aqueous solubility of noladin ether (>40000-fold), showed
Amanda R Wilmsmeyer et al.
Langmuir : the ACS journal of surfaces and colloids, 28(30), 10962-10967 (2012-07-12)
The fundamental interactions of dimethyl methylphosphonate (DMMP) and dimethyl chlorophosphate (DMCP) on amorphous silica nanoparticles have been investigated with transmission infrared spectroscopy and temperature-programmed desorption (TPD). DMMP and DMCP both adsorb molecularly to silica through the formation of hydrogen bonds
Minji Kang et al.
ACS applied materials & interfaces, 11(8), 7686-7694 (2019-02-16)
Quorum sensing (QS) inhibitor-based therapy is an attractive strategy to inhibit bacterial biofilm formation without excessive induction of antibiotic resistance. Thus, we designed Ca2+-binding poly(lactide- co-glycolide) (PLGA) microparticles that can maintain a sufficient concentration of QS inhibitors around hydroxyapatite (HA)

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