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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:
683-08-9
Molecular Weight:
152.13
Beilstein:
1753416
EC Number:
211-667-4
MDL number:
MFCD00009813
UNSPSC Code:
12352108
PubChem Substance ID:
24856263
NACRES:
NA.22
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Quality Level

100

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.)

functional group

phosphonate

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,[1] γ-hydroxyl,[2] and dialkyl fluoroalkynyl[3] phosphonates.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6030
SHBS0183
SHBN8292
SHBN0582
SHBL0569

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Synthetic Communications, 21, 2341-2341 (1991)
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
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
The Journal of Organic Chemistry, 58, 5779-5779 (1993)
Journal of the Chemical Society. Perkin Transactions 1, 2153-2153 (1993)
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