ethyl 2-cyanoacetate

• ChemBase ID: 85658
• Molecular Formular: C5H7NO2
• Molecular Mass: 113.11458
• Monoisotopic Mass: 113.04767847
• SMILES: N#CCC(=O)OCC
• Canonical SMILES: CCOC(=O)CC#N
• InChI: InChI=1S/C5H7NO2/c1-2-8-5(7)3-4-6/h2-3H2,1H3
• InChIKey: ZIUSEGSNTOUIPT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-cyanoacetate
• IUPAC Traditional name: ethyl cyanoacetate
• Synonyms: Ethyl cyanoacetate; Cyanoacetic acid ethyl ester; Ethyl cyanoacetate; ethyl 2-cyanoacetate; 氰乙酸乙酯; 氰基乙酸乙酯

Database IDs

• CAS Number: 105-56-6
• EC Number: 203-309-0
• MDL Number: MFCD00001940
• Beilstein Number: 605871
• Merck Index: 143786
• PubChem SID: 24894436; 24865300; 162072774
• PubChem CID: 7764

CALCULATED PROPERTIES

• Acid pKa: 8.98093
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.22939037
• LogD (pH = 7.4): 0.21830069
• Log P: 0.22953361
• Molar Refractivity: 27.4848 cm^3
• Polarizability: 10.614262 Å^3
• Polar Surface Area: 50.09 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -22 °C(lit.); -22°C; -23°C; -23°C
• Boiling Point: 208°C; 208-210 °C(lit.); 208-210°C; 208-210°C
• Flash Point: 109 °C; 109°C; 109°C(228°F); 228.2 °F
• Density: 1.0560 g/ml; 1.063; 1.063 g/mL at 25 °C(lit.)
• Refractive Index: 1.4180; n20/D 1.418; n20/D 1.418(lit.)
• Vapor Pressure: 1 mmHg ( 67.8 °C)
• Vapor Density: 3.9 (vs air)

Safety Information

• Storage Warning: Harmful
• RTECS: AG4110000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 20/21/22; 36; R:36
• Safety Statements: 23-26; 36/37; S:26
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332; H319
• GHS Precautionary statements: P261-P305+P351+P338; P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥98%; ≥98.0% (GC); ≥99%; ≥99.5% (GC); 95+%; 97%; 98+%
• Grade: analytical standard; purum
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: NCCH2COOC2H5

DETAILS

Sigma Aldrich - 241202

Packaging
50 g in glass bottle

Sigma Aldrich - E18425

Packaging
1 kg in glass bottle
5, 250 g in glass bottle

REFERENCES

• For use in the synthesis of pyrrole derivatives, see p-Toluenesulfonylmethyl isocyanide, A14312.
• Stereoselective alkylation of the active methylene has been accomplished under particularly mild conditions with secondary alkyl mesylates in the presence of CsF in DMF; complete inversion occurs at the secondary alkyl carbon: J. Org. Chem., 60, 2627 (1995).
• Arylation by aryl iodides is promoted by copper(I) iodide: Synthesis, 67 (1983); J. Org. Chem., 58, 7606 (1993); or trans-Dichlorobis(triphenylphosphine)palladium(II), 10491: Synthesis, 506 (1985).
• For examples of Knoevenagel condensations of cyanoacetic esters with carbonyl compounds, see: Org. Synth. Coll., 3, 385, 399 (1955); 4, 93, 463 (1963); review: Org. React., 15, 204 (1967). Knoevenagel condensation with aromatic aldehydes has also been carried out under acidic conditions, for example, good yields have been obtained with ZnCl₂: Tetrahedron Lett., 32, 5821 (1991).