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105-56-6 molecular structure
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ethyl 2-cyanoacetate

ChemBase ID: 85658
Molecular Formular: C5H7NO2
Molecular Mass: 113.11458
Monoisotopic Mass: 113.04767847
SMILES and InChIs

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

Cite this record

CBID:85658 http://www.chembase.cn/molecule-85658.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 8.98093  H Acceptors
H Donor LogD (pH = 5.5) 0.22939037 
LogD (pH = 7.4) 0.21830069  Log P 0.22953361 
Molar Refractivity 27.4848 cm3 Polarizability 10.614262 Å3
Polar Surface Area 50.09 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
-22 °C(lit.) expand Show data source
-22°C expand Show data source
-23°C expand Show data source
-23°C expand Show data source
Boiling Point
208°C expand Show data source
208-210 °C(lit.) expand Show data source
208-210°C expand Show data source
208-210°C expand Show data source
Flash Point
109 °C expand Show data source
109°C expand Show data source
109°C(228°F) expand Show data source
228.2 °F expand Show data source
Density
1.0560 g/ml expand Show data source
1.063 expand Show data source
1.063 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.4180 expand Show data source
n20/D 1.418 expand Show data source
n20/D 1.418(lit.) expand Show data source
Vapor Pressure
1 mmHg ( 67.8 °C) expand Show data source
Vapor Density
3.9 (vs air) expand Show data source
Storage Warning
Harmful expand Show data source
RTECS
AG4110000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Risk Statements
20/21/22 expand Show data source
36 expand Show data source
R:36 expand Show data source
Safety Statements
23-26 expand Show data source
36/37 expand Show data source
S:26 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H312-H332 expand Show data source
H319 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338 expand Show data source
P280 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
Purity
≥98% expand Show data source
≥98.0% (GC) expand Show data source
≥99% expand Show data source
≥99.5% (GC) expand Show data source
95+% expand Show data source
97% expand Show data source
98+% expand Show data source
Grade
analytical standard expand Show data source
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Linear Formula
NCCH2COOC2H5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 241202 external link
Packaging
50 g in glass bottle
Sigma Aldrich - E18425 external link
Packaging
1 kg in glass bottle
5, 250 g in glass bottle

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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