diethyl (isocyanomethyl)phosphonate

• ChemBase ID: 146431
• Molecular Formular: C6H12NO3P
• Molecular Mass: 177.138141
• Monoisotopic Mass: 177.05547988
• SMILES: CCOP(=O)(C[N+]#[C-])OCC
• Canonical SMILES: CCOP(=O)(C[N+]#[C-])OCC
• InChI: InChI=1S/C6H12NO3P/c1-4-9-11(8,6-7-3)10-5-2/h4-6H2,1-2H3
• InChIKey: ICURVXBGGDVHDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (isocyanomethyl)phosphonate
• IUPAC Traditional name: diethyl isocyanomethylphosphonate
• Synonyms: Isocyanomethylphosphonic acid diethyl ester; Diethyl isocyanomethylphosphonate; 异腈甲基膦酸二乙酯

Database IDs

• CAS Number: 41003-94-5
• MDL Number: MFCD00042951
• Beilstein Number: 4674920
• PubChem SID: 24881211; 162240627; 24862114
• PubChem CID: 2734699

CALCULATED PROPERTIES

• Acid pKa: 16.071178
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -1.2552258
• LogD (pH = 7.4): -1.2552258
• Log P: -1.2552258
• Molar Refractivity: 50.5501 cm^3
• Polarizability: 16.85962 Å^3
• Polar Surface Area: 39.89 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 84-87 °C/0.1 mmHg(lit.)
• Flash Point: 113 °C; 235 °F; 235.4 °F
• Density: 1.105 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.433(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38; 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302 + H312 + H332-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: >97% (GC); ≥97.0% (GC); 97%
• Grade: purum
• Linear Formula: CNCH2P(O)(OC2H5)2

DETAILS

Sigma Aldrich - I0514

Application
Precursor for synthesis of phosphonic acid analogs of α-amino acids.
Reactant for:
• Copper-catalyzed cycloaddition reactions1
• Preparation of orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase2
• Synthesis of sterol analogs as antifungal agents against plant pathogens3
• Asymmetric synthesis of steroidal 2,5-diketopiperazines prepared via isocyanide chemistry based on stereoselective Ugi four component condensation and subsequent cyclocondensation reactions4
• The Passerini reaction5

Sigma Aldrich - 359866

Packaging
1 mL in glass bottle
Application
Reactant for:
• Copper-catalyzed cycloaddition reactions1
• Preparation of orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase2
• Synthesis of sterol analogs as antifungal agents against plant pathogens3
• Asymmetric synthesis of steroidal 2,5-diketopiperazines prepared via isocyanide chemistry based on stereoselective Ugi four component condensation and subsequent cyclocondensation reactions4
• The Passerini reaction5

Sigma Aldrich - 58833

Other Notes
Prep. of phosphonic acid analogs of amino acids6,7,8; Synthesis of aldehydes from carbonyl compounds9,10
Application
Reactant for:
• Copper-catalyzed cycloaddition reactions1
• Preparation of orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase2
• Synthesis of sterol analogs as antifungal agents against plant pathogens3
• Asymmetric synthesis of steroidal 2,5-diketopiperazines prepared via isocyanide chemistry based on stereoselective Ugi four component condensation and subsequent cyclocondensation reactions4
• The Passerini reaction5