ethyl 2-isocyanoacetate

• ChemBase ID: 78318
• Molecular Formular: C5H7NO2
• Molecular Mass: 113.11458
• Monoisotopic Mass: 113.04767847
• SMILES: [N+](#[C-])CC(=O)OCC
• Canonical SMILES: [C-]#[N+]CC(=O)OCC
• InChI: InChI=1S/C5H7NO2/c1-3-8-5(7)4-6-2/h3-4H2,1H3
• InChIKey: FPULFENIJDPZBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-isocyanoacetate
• IUPAC Traditional name: ethyl 2-isocyanoacetate
• Synonyms: Ethyl isocyanoacetate; ethyl 2-isocyanoacetate; Isocyanoacetic acid ethyl ester; Ethyl isocyanoacetate; 异氰基乙酸乙酯; 异氰乙酸乙酯

Database IDs

• CAS Number: 2999-46-4
• EC Number: 221-077-9
• MDL Number: MFCD00000007
• Beilstein Number: 3588613
• PubChem SID: 24853557; 162043087; 24881207
• PubChem CID: 533707

CALCULATED PROPERTIES

• Acid pKa: 16.10355
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -1.9777237
• LogD (pH = 7.4): -1.9777237
• Log P: -1.9777237
• Molar Refractivity: 37.1139 cm^3
• Polarizability: 11.067871 Å^3
• Polar Surface Area: 30.66 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 194-196 °C(lit.); 194-196°C; 194-196°C
• Flash Point: 183.2 °F; 84 °C; 84°C; 84°C(183°F)
• Density: 1.035; 1.035 g/mL at 25 °C(lit.)
• Refractive Index: 1.4220; n20/D 1.418; n20/D 1.418(lit.)
• Hydrophobicity(logP): -0.067

Safety Information

• Storage Warning: Moisture & Light Sensitive; Toxic/Moisture Sensitive/Light Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2810; UN2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 20/21/22-36/37/38; 20/22
• Safety Statements: 9-26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H332; H331-H302-H312-H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 95%; 98%
• Grade: purum
• Linear Formula: CNCH2COOCH2CH3

DETAILS

Sigma Aldrich - 226319

Application
Cyclization synthon used to prepare pyrroles,1,2 oxazolines,3 benzodiazepines,4 oxazoles5 and imidazoles.6
General description
Material may darken upon storage
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 58822

Caution
discolors to brown on storage
Other Notes
Reviews1,2; Synthesis of α-amino acids3

REFERENCES

• The method has been extended to nitroaromatics, leading to pyrroles and porphyrins fused with aromatic rings: J. Chem. Soc., Perkin 1, 417 (1996).
• Base-catalyzed Michael addition to nitroalkenes provides a route to substituted pyrroles, valuable as intermediates for porphyrin synthesis: J. Chem. Soc., Chem. Commun., 1098 (1985); Tetrahedron, 46, 7483, 7587 (1990); Org. Synth. Coll., 9, 242 (1998).
• The terminal carbon also undergoes nucleophilic attack on an acyl chloride to give an ɑ-keto imidoyl chloride, which cyclizes in base to a 2-acyl-5-ethoxy oxazole: Synth. Commun., 26, 1149 (1996).