Ethyl cyanoacetate

• Formula: C₅H₇NO₂
• Molecular weight: 113.1146
• IUPAC Standard InChI: InChI=1S/C5H7NO2/c1-2-8-5(7)3-4-6/h2-3H2,1H3 Copy

  
• IUPAC Standard InChIKey: ZIUSEGSNTOUIPT-UHFFFAOYSA-N Copy
• CAS Registry Number: 105-56-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Acetic acid, cyano-, ethyl ester; Cyanoacetic acid, ethyl ester; Cyanoacetic ester; Ethyl cyanacetate; Ethyl cyanoethanoate; Malonic acid, ethyl ester nitrile; NCCH2COOC2H5; Cyanacetate ethyle; USAF KF-25; Estere cianoacetico; Ethylester kyseliny kyanoctove; UN 2666; Ethyl ester of cyanoacetic acid; Acetic acid, 2-cyano-, ethyl ester; NSC 8844
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of fusion

Temperature of phase transition

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₅H₆NO₂^- +  =

By formula: C₅H₆NO₂^- + H⁺ = C₅H₇NO₂

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Guinchant, 1918
Guinchant, M.J., Etude sur la fonction acide dans les derives metheniques et methiniques, Ann. Chem., 1918, 10, 30-84. [all data]

Iskhakov, Ismailov, et al., 1991
Iskhakov, B.G.; Ismailov, T.S.; Khodzhaeva, M.G.; Igamberdyev, Kh.T.; Mamadalimov, A.T., Heat capacity of cyanoacetic acid ethyl ester, Inzh.-Fiz. Zh., 1991, 61(3), 427-430. [all data]

Khodzhaeva, Bugakov, et al., 1987
Khodzhaeva, M.G.; Bugakov, Yu.V.; Ismailov, T.S., Heat capacity and thermodynamic functions of ethyl cyanoacetate, Khim.-Farm. Zhur., 1987, 21, 760-762. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Popp, 1964
Popp, F.D., Some Derivatives of 3-Bromobenzaldehyde, J. Chem. Eng. Data, 1964, 9, 381. [all data]

Iskhakov, Ismailov, et al., 1991, 2
Iskhakov, B.G.; Ismailov, T.S.; Khodzhaeva, M.G.; Igamberdyev, K.T.; Mamadalimov, A.T., Heat capacity of cyanoacetic acid ethyl ester, Inzh.-Fiz. Zh., 1991, 61, 427-30. [all data]

Khodzhaeva, Bugakov, et al., 1987, 2
Khodzhaeva, M.G.; Bugakov, Yu.V.; Ismailov, T.S., Heat capacity and thermodynamic functions of ethyl cyanoacetate, Khim.-Farm. Zh., 1987, 21, 760-2. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Ttrs	Temperature of phase transition
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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