Propanedinitrile

• Formula: C₃H₂N₂
• Molecular weight: 66.0614
• IUPAC Standard InChI: InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 Copy

  
• IUPAC Standard InChIKey: CUONGYYJJVDODC-UHFFFAOYSA-N Copy
• CAS Registry Number: 109-77-3
• 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: Malononitrile; Cyanoacetonitrile; Dicyanomethane; Malonic acid dinitrile; Malonodinitrile; Methane, dicyano-; Methylene cyanide; Methylenedinitrile; CH2(CN)2; Malonitrile; Malonic dinitrile; Nitril kyseliny malonove; USAF A-4600; Dwumetylosulfotlenku; Rcra waste number U149; UN 2647; USAF KF-19; NSC 3769
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• Information on this page:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Phase change data

Go To: Top, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of fusion

Temperature of phase transition

Enthalpy of phase transition

Entropy of phase transition

IR Spectrum

Go To: Top, Phase change data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

• LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• LIQUID (NEAT) $$PURITY 99.75%; BAIRD (PRISM); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY
• SOLID (MULL, KEL-F OIL FOR 2-7.5 AND MINERAL OIL FOR 7.5-16 MICRONS); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution

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, Phase change 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.

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

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Stephenson, 1994
Stephenson, R.M., Mutual Solubility of Water and Nitriles, J. Chem. Eng. Data, 1994, 39, 225-7. [all data]

Trunel, 1939
Trunel, P., Electric Moments in Several Homologous Series of Organic Compounds, Ann. Chim. (Paris), 1939, 12, 110. [all data]

Van de Vloed, 1939
Van de Vloed, A., Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]

Bruhl, 1895
Bruhl, J.W., Spectrochemistry of Nitrogen-Containing Compounds. I., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1895, 16, 193. [all data]

Girdhar, Westrum, et al., 1968
Girdhar, H.L.; Westrum, E.F.; Wulff, C.A., Thermodynamic properties and third-law cycle for malononitrile., J. Chem. Eng. Data, 1968, 13, 239-42. [all data]

Westrum and Wulff, 1968
Westrum, E.F.; Wulff, C.A., Thermodynamic properties and third-law cycle for malononitrile, J. Chem. Eng. Data, 1968, 13, 239. [all data]

Beckhaus, Dogan, et al., 1990
Beckhaus, H.D.; Dogan, B.; Pakusch, J.; Verevkin, S.; Ruechardt, C., Geminal substituent effects. 4. The dependence of the inverse anomeric effect of geminal cyano groups on the structure, Chem. Ber., 1990, 123, 2153-2159. [all data]

Boyd, Guha, et al., 1967
Boyd, R.H.; Guha, K.R.; Wuthrich, R., Thermochemistry of cyanocarbons. II. The heats of combustion of pyridinium dicyanomethylide, malononitrile, and fumaronitrile, J. Phys. Chem., 1967, 71, 2187-2191. [all data]

Badea, Blanco, et al., 2007
Badea, Elena; Blanco, Ignazio; Della Gatta, Giuseppe, Fusion and solid-to-solid transitions of a homologous series of alkane-α,ω-dinitriles, The Journal of Chemical Thermodynamics, 2007, 39, 10, 1392-1398, https://doi.org/10.1016/j.jct.2007.03.005 . [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]

Wasiutynski, Olejarczyk, et al., 1987
Wasiutynski, T.; Olejarczyk, W.; Sciesinski, J.; Witko, W., Phase transition studies of malononitrile, J. Phys. C: Solid State Phys., 1987, 20, L65-L69. [all data]

Girdhar, Westrum, et al., 1968, 2
Girdhar, H.L.; Westrum, E.F., Jr.; Wulff, C.A., Thermodynamic properties and third-law cycle for malononitrile, J. Chem. Eng. Data, 1968, 13, 239-242. [all data]

Notes

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

• Symbols used in this document:
  

  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
  ΔfusH	Enthalpy of fusion
  ΔsubH°	Enthalpy of sublimation at standard conditions

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