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Key Documents

I0514

Sigma-Aldrich

Diethyl isocyanomethylphosphonate

>97% (GC)

Synonym(s):

Isocyanomethylphosphonic acid diethyl ester

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About This Item

Linear Formula:
CNCH2P(O)(OC2H5)2
CAS Number:
Molecular Weight:
177.14
Beilstein:
4674920
MDL number:
UNSPSC Code:
12352000

Assay

>97% (GC)

refractive index

n20/D 1.433 (lit.)

bp

84-87 °C/0.1 mmHg (lit.)

density

1.105 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOP(=O)(C[N+]#[C-])OCC

InChI

1S/C6H12NO3P/c1-4-9-11(8,6-7-3)10-5-2/h4-6H2,1-2H3

InChI key

ICURVXBGGDVHDT-UHFFFAOYSA-N

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Application

Reactant for:
  • Copper-catalyzed cycloaddition reactions
  • Preparation of orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase
  • Synthesis of sterol analogs as antifungal agents against plant pathogens
  • Asymmetric synthesis of steroidal 2,5-diketopiperazines prepared via isocyanide chemistry based on stereoselective Ugi four component condensation and subsequent cyclocondensation reactions
  • The Passerini reaction
Precursor for synthesis of phosphonic acid analogs of α-amino acids.

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Rachon, J.
Synthesis, 219-219 (1984)
Schollkopf, U. and Wintel, T.
Synthesis, 1033-1033 (1984)

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