methyl 2-isocyanoacetate

• ChemBase ID: 150689
• Molecular Formular: C4H5NO2
• Molecular Mass: 99.088
• Monoisotopic Mass: 99.03202841
• SMILES: COC(=O)C[N+]#[C-]
• Canonical SMILES: [C-]#[N+]CC(=O)OC
• InChI: InChI=1S/C4H5NO2/c1-5-3-4(6)7-2/h3H2,2H3
• InChIKey: CRXFROMHHBMNAB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-isocyanoacetate
• IUPAC Traditional name: methyl 2-isocyanoacetate
• Synonyms: Methyl isocyanoacetate; 异氰基乙酸甲酯

Database IDs

• CAS Number: 39687-95-1
• EC Number: 254-593-8
• MDL Number: MFCD00000006
• Beilstein Number: 3537963
• PubChem SID: 162244850; 24854350; 24881209
• PubChem CID: 547815

CALCULATED PROPERTIES

• Acid pKa: 16.10355
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -2.3345315
• LogD (pH = 7.4): -2.3345315
• Log P: -2.3345315
• Molar Refractivity: 32.3653 cm^3
• Polarizability: 9.244844 Å^3
• Polar Surface Area: 30.66 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 75-76 °C/10 mmHg(lit.)
• Flash Point: 183.2 °F; 84 °C
• Density: 1.09 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.417(lit.); n20/D 1.418

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 2922
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 20/21/22-34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H312-H314-H332
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (GC); 95%
• Grade: purum; technical grade
• Shipped in: wet ice
• Linear Formula: CNCH2COOCH3

DETAILS

Sigma Aldrich - 238880

Application
Used in the copper-catalyzed, diastereoselective synthesis of oxazolines.1
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 58830

Caution
discolor to brown-yellow on storage
Other Notes
Review1