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268119

Sigma-Aldrich

Diethyl methylphosphonate

97%

Synonym(s):
Bis(diethoxyphosphinyl)methane, Diethoxymethylphosphine oxide, DEMP
Linear Formula:
CH3P(O)(OC2H5)2
CAS Number:
Molecular Weight:
152.13
Beilstein:
1753416
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Reagent employed in the synthesis of α-alkenyl, γ-hydroxyl, and dialkyl fluoroalkynyl phosphonates.
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

Packaging

5, 25 g in glass bottle

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Synthetic Communications, 21, 2341-2341 (1991)
The Journal of Organic Chemistry, 58, 5779-5779 (1993)
Journal of the Chemical Society. Perkin Transactions 1, 2153-2153 (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
Ying Zhang et al.
Biomaterials, 26(33), 6736-6742 (2005-06-07)
Novel BAB type amphiphilic triblock copolymers consisting of poly (ethylene glycol) (PEG) (B) as hydrophilic segment and poly (epsilon-caprolactone) (PCL) (A) as hydrophobic block were prepared by coupling reaction using L-lysine methyl ester diisocyanate (LDI) as the chain extender. The

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