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58833 Sigma-Aldrich

Diethyl isocyanomethylphosphonate

purum, ≥97.0% (GC)

Synonym: Isocyanomethylphosphonic acid diethyl ester

  • CAS Number 41003-94-5

  • Linear Formula CNCH2P(O)(OC2H5)2

  • Molecular Weight 177.14

  •  Beilstein Registry Number 4674920

  •  MDL number MFCD00042951

  •  PubChem Substance ID 329758494

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Properties

Related Categories C-C Bond Formation, Chemical Synthesis, Horner-Wadsworth-Emmons Reagents, Olefination, Synthetic Reagents More...
InChI Key   ICURVXBGGDVHDT-UHFFFAOYSA-N
grade   purum
assay   ≥97.0% (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

Description

Other Notes

Prep. of phosphonic acid analogs of amino acids; Synthesis of aldehydes from carbonyl compounds

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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

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C
Protocols & Articles
Peer-Reviewed Papers
15

References

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