Ethyl cyanoacetate

An ester, C5H7NO2, 113.116 g/mol. Boiling point 205 °C, melting point -22.5 °C, as published.

verified recordOrganic — ester7 measured properties

Identifiers

Molecular formula: C₅H₇NO₂
Molecular weight: 113.116 g/mol
Exact mass: 113.047678 g/mol
IUPAC name: ethyl 2-cyanoacetate
SMILES: CCOC(=O)CC#N
InChI: InChI=1S/C5H7NO2/c1-2-8-5(7)3-4-6/h2-3H2,1H3
InChIKey: ZIUSEGSNTOUIPT-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: 205 °Cmeasured · Hazardous Substances Data Bank (HSDB); BP: 206.00 °C at 750 mm Hg; 152.8 °C at 100 mm Hg; 133.8 °C at 40 mm Hg; 119.8 °C at 20 mm Hg; 106.0 °C at 10 mm Hg; 93.5 °C at 5 mm Hg; 67.8 °C at 1.0 mm Hgmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point: -22.5 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.0654 g/cu cm at 20 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility: Very soluble in ethyl ether, ethanolmeasured · Hazardous Substances Data Bank (HSDB); Soluble in ammonia water, aqueous solution of alkalies; miscible with alcohol, ethermeasured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 0.03 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases; VP: 1 mm Hg at 67.8 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Flash Point: 230 °F (NFPA, 2010)measured · CAMEO Chemicals; 230 °Fmeasured · Hazardous Substances Data Bank (HSDB)
Refractive Index: Index of refraction = 1.4175 at 20 °C/Dmeasured · Lide, D.R. CRC Handbook of Chemistry and Physics 88TH Edition 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, p. 3-240; Index of refraction: 1.41793 at 20.5 °C/Dmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 648

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 113.11 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 113.047678466 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 0.4calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 50.1 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 122calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 0calculated · reference compound database
H-bond acceptors: 3calculated · reference compound database
logP: 0.4632calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 50.09 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 0calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 3calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 2calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 26.863 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.6calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.4887calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon5 atoms · 53.1% by mass
O Oxygen2 atoms · 28.3% by mass
N Nitrogen1 atom · 12.4% by mass
H Hydrogen7 atoms · 6.2% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 8
Total atoms, hydrogen included: 15
Rings: 0
Aromatic rings: 0
Stereocentres: 0
Formal charge: 0

Functional groups

Ester
A carbonyl bonded to an oxygen that links to another carbon.
Ether
An oxygen bridging two carbons.
Nitrile
A carbon–nitrogen triple bond.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Ethyl cyanoacetate yet.

Other names for it

The systematic name on this record is ethyl 2-cyanoacetate.

The sources also call it Ethyl 2-cyanoacetate, Ethyl cyanacetate, Cyanoacetic acid ethyl ester, Cyanoacetic ester, Ethyl cyanoethanoate, Acetic acid, cyano-, ethyl ester, Cyanacetate ethyle, USAF KF-25, Estere cianoacetico, Malonic acid ethyl ester nitrile, Ethylester kyseliny kyanoctove.

Structurally related

Nothing structurally close to Ethyl cyanoacetate has a page here yet.

Where these values came from

reference compound database7764
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.