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268119

Sigma-Aldrich

Diethyl methylphosphonate

97%

Synonym(s):

Bis(diethoxyphosphinyl)methane, DEMP, Diethoxymethylphosphine oxide

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About This Item

Linear Formula:
CH3P(O)(OC2H5)2
CAS Number:
Molecular Weight:
152.13
Beilstein:
1753416
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.414 (lit.)

bp

194 °C (lit.)

density

1.041 g/mL at 25 °C (lit.)

SMILES string

CCOP(C)(=O)OCC

InChI

1S/C5H13O3P/c1-4-7-9(3,6)8-5-2/h4-5H2,1-3H3

InChI key

NYYLZXREFNYPKB-UHFFFAOYSA-N

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Application

Reactant for the synthesis of:
  • Fluoroalkyl α- and β-aminophosphonates
  • Acyclic nucleoside phosphonates with branched phosphonoethoxy-Et chains as potential antivirals
  • Difluoromethyl arylphosphonates
  • Pyridone alkaloids with neuritogenic activity
  • Lipophilic meropenem-derived prodrugs
  • Phomactin cyclohexane core and diterpenoid framework
  • Phosphonylated peptides via solid-phase synthesis
Reagent employed in the synthesis of α-alkenyl, γ-hydroxyl, and dialkyl fluoroalkynyl phosphonates.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Journal of the Chemical Society. Perkin Transactions 1, 2153-2153 (1993)
Synthetic Communications, 21, 2341-2341 (1991)
The Journal of Organic Chemistry, 58, 5779-5779 (1993)
E Maurelli et al.
Free radical biology & medicine, 27(1-2), 34-41 (1999-08-12)
The spin trap 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) is an improved ESR probe to assess superoxide (O2*-) formation in the postischemic heart. We recently found that DEPMPO pretreatment improves recovery of cardiac function with the concomitant inhibition of postischemic O2*- production. By
Q Li et al.
Toxicology letters, 98(1-2), 95-103 (1998-10-17)
More than 5000 passengers of Tokyo subway trains were injured with toxic chemicals including the nerve gas sarin. Most of the victims examined had marked miosis and decreased serum cholinesterase activity. To monitor the genetic aftereffects of sarin exposure, we

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