p-Cymene

• Formula: C₁₀H₁₄
• Molecular weight: 134.2182
• IUPAC Standard InChI: InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 Copy

  
• IUPAC Standard InChIKey: HFPZCAJZSCWRBC-UHFFFAOYSA-N Copy
• CAS Registry Number: 99-87-6
• 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.
• Isotopologues:
  • d14 Cymene
• Other names: Benzene, 1-methyl-4-(1-methylethyl)-; p-Cimene; p-Cymol; p-Isopropyltoluene; p-Methylisopropylbenzene; Camphogen; Dolcymene; 1-Isopropyl-4-methylbenzene; 1-Methyl-4-isopropylbenzene; 2-p-Tolylpropane; 4-Isopropyl-1-methylbenzene; 1-Methyl-4-(1-methylethyl)-benzene; Benzene, 1-isopropyl-4-methyl-; Cumene, p-methyl-; p-Isopropylmethylbenzene; Paracymene; Paracymol; p-Methylcumene; 4-Isopropyltoluene; 4-Methylisopropylbenzene; 1-(1-methylethyl)-4-methylbenzene; benzene, 1-methyl-4-methylethyl-; p-Mentha-1,3,5-triene; NSC 4162; Cymene; Cymol
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Normal boiling point
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Normal boiling point

Go To: Top, 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

References

Go To: Top, Normal boiling point, Notes

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

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]

Hartmann and Jaenicke, 1959
Hartmann, H.; Jaenicke, R., Z. Phys. Chem. (Munich), 1959, 19, 327. [all data]

Kieffer and Holroyd, 1955
Kieffer, W.F.; Holroyd, R.A., Azeotropes of 2-Butoxyethanol with Alkylbenzenes, Ind. Eng. Chem., 1955, 47, 457-8. [all data]

Imoto, Huang, et al., 1954
Imoto, M.; Huang, C.-Y.; Adachi, A., Kogyo Kagaku Zasshi, 1954, 57, 458. [all data]

Pines, Olberg, et al., 1952
Pines, H.; Olberg, R.C.; Ipatieff, V.N., J. Am. Chem. Soc., 1952, 74, 4872. [all data]

Tishchenko and Summ, 1952
Tishchenko, D.; Summ, N., New Transformation Type in Terpenes VI. Action of Chlorine on α-Terpinene, Zh. Obshch. Khim., 1952, 22, 798-802. [all data]

Anonymous, 1951
Anonymous, R., , Sunbury Rep. No. 4199, Anglo-Iranian Oil Co., 1951. [all data]

Roberts and Good, 1951
Roberts, R.M.; Good, G.M., Effect of Nuclear Substitution on the Rate of SIlica-Zirconia-Alumina- Catalyzed Depropylation of Cumene, J. Am. Chem. Soc., 1951, 73, 1320. [all data]

Petrov and Sopov, 1950
Petrov, A.A.; Sopov, N.P., Dokl. Akad. Nauk SSSR, 1950, 79, 811. [all data]

Birch, Dean, et al., 1949
Birch, S.F.; Dean, R.A.; Fidler, F.A.; Lowry, R.A., The preparation of the c(10) monocyclic aromatic hydrocarbons, J. Am. Chem. Soc., 1949, 71, 1362. [all data]

Foehr and Fenske, 1949
Foehr, E.G.; Fenske, M.R., Magneto-optic Rotation of Hydrocarbons, Ind. Eng. Chem., 1949, 41, 1956. [all data]

Birch, 1948
Birch, S.F., Unpublished, 1948, Anglo-Iranian Oil Co., 1948. [all data]

Anonymous, 1947
Anonymous, R., , Am. Pet. Inst. Res. Proj. 45, Ohio State Univ., 1947. [all data]

Balandin and Marukyan, 1947
Balandin, A.A.; Marukyan, G.M., Dokl. Akad. Nauk SSSR, 1947, 55, 121. [all data]

Fenske, Braun, et al., 1947
Fenske, M.R.; Braun, W.G.; Wiegand, R.V.; Quiggle, D.; McCormick, R.H.; Rank, D.H., Raman Spectra of Hydrocarbons, Anal. Chem., 1947, 19, 700. [all data]

Anonymous, 1946
Anonymous, R., , Am. Pet. Inst. Res. Proj. 45, Ohio State Univ., 1946. [all data]

Gibbons, Thompson, et al., 1946
Gibbons, L.C.; Thompson, J.F.; Reynolds, T.W.; Wright, J.I.; Chanan, H.H.; Lamberti, J.M.; Hipsher, H.F.; Karabinos, J.V., The Purification and Physical Constants of Aromatic Compounds, J. Am. Chem. Soc., 1946, 68, 1130. [all data]

Smith and Pennekamp, 1945
Smith, H.A.; Pennekamp, E.F.H., The Catalytic Hydrogenation of the Benzene Nucleus III. The Hydrogenation of Polymethylbenzenes, J. Am. Chem. Soc., 1945, 67, 279. [all data]

Simons and Hart, 1944
Simons, J.H.; Hart, H., Hydrogen Chloride as a Condensing Agent, J. Am. Chem. Soc., 1944, 66, 1309. [all data]

Anonymous, 1943
Anonymous, R., , Sunbury Rep. No. 2176, Anglo-Iranian Oil Co., 1943. [all data]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]

Kobe, Okabe, et al., 1941
Kobe, K.A.; Okabe, T.S.; Ramstad, M.T.; Huemmer, P.M., p-Cymene Studies. VI. Vapor Pressure of p-Cymene, Some of its Derivatives and Related Compounds, J. Am. Chem. Soc., 1941, 63, 3251. [all data]

Ipatieff, Corson, et al., 1936
Ipatieff, V.N.; Corson, B.B.; Pines, H., Influence of Sulfuric Acid Concentration upon Reaction between Olefins and Benzene, J. Am. Chem. Soc., 1936, 58, 919-22. [all data]

Le Fevre, Le Fevre, et al., 1935
Le Fevre, C.G.; Le Fevre, R.J.W.; Robertson, K.W., The dipole moments of p-cymene; 2- and 3-halogeno-p-cymenes, carvacrol, and thymol; p-ethyltoluene; p-tert-butyltoluene, 1,3-dimethyl-5-tert- butylbenzene, tert-butylbenzene and its p-nitro-derivativ, J. Chem. Soc. 480 1935, 1935. [all data]

Mulliken and Wakeman, 1935
Mulliken, S.P.; Wakeman, R.L., A study of the relation between the structure of hydrocarbons and their miscibility with selective solvents, Recl. Trav. Chim. Pays-Bas, 1935, 54, 366-72. [all data]

Ward and Fulweiler, 1934
Ward, A.L.; Fulweiler, W.H., Ind. Eng. Chem., Anal. Ed., 1934, 6, 396. [all data]

Bulkley, 1931
Bulkley, R., J. Res. Natl. Bur. Std., 1931, 6, 89. [all data]

Huffman, Parks, et al., 1931
Huffman, H.M.; Parks, G.S.; Barmore, M., Thermal Data on Organic Compounds X. Further Studies on the Heat Capacities, Entropies, and Free Energies of Hydrocarbons, J. Am. Chem. Soc., 1931, 53, 3876-88. [all data]

Richter and Wolff, 1930
Richter, F.; Wolff, W., Chem. Ber., 1930, 63, 1714. [all data]

Richter and Wolff, 1930, 2
Richter, F.; Wolff, W., Chem. Ber., 1930, 63, 1721. [all data]

Lacourt, 1929
Lacourt, A., Bull. Soc. Chim. Belg., 1929, 38, 1. [all data]

Lecat, 1927
Lecat, M., New binary azeotropes: 6th list, Ann. Soc. Sci. Bruxelles, Ser. B, 1927, 47, 63-71. [all data]

Eisenlohr and Schulz, 1924
Eisenlohr, F.; Schulz, L., Ber. Dtsch. Chem. Ges., 1924, 57, 1816-20. [all data]

Grimm and Patrick, 1923
Grimm, F.V.; Patrick, W.A., The Dielectric Constastants of Organic Liquids at the Boilin Point, J. Am. Chem. Soc., 1923, 45, 2794. [all data]

Skita and Schneck, 1922
Skita, A.; Schneck, A., Stereoismerism in Cyclic Hydrocarbons, Chem. Ber., 1922, 55, 144-52. [all data]

Rechenberg, 1921
Rechenberg, C.V., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1921, 99, 89. [all data]

Timmermans, 1921
Timmermans, J., The Freezing Points of Organic Substances IV. New Exp. Determinations, Bull. Soc. Chim. Belg., 1921, 30, 62. [all data]

Von Auwers, 1919
Von Auwers, K., Connections between constitution and physical properties of hydrocarbons of the benzene series., Justus Liebigs Ann. Chem., 1919, 419, 92. [all data]

Lagerlof, 1918
Lagerlof, D., Thermodynamic research: reduced formulas for simplified calculations of latent molar heat of evaporation, J. Prakt. Chem., 1918, 98, 136. [all data]

Wallach and Berthold, 1918
Wallach, O.; Berthold, H., Justus Liebigs Ann. Chem., 1918, 414, 210. [all data]

Schorger, 1917
Schorger, A.W., J. Am. Chem. Soc., 1917, 39, 2671. [all data]

Sabatier and Murat, 1913
Sabatier, P.; Murat, M., Preparation of Three Cymenes and Thre Menthanes, C. R. Hebd. Seances Acad. Sci., 1913, 156, 184. [all data]

Sabatier and Murat, 1913, 2
Sabatier, P.; Murat, M., C. R. Hebd. Seances Acad. Sci., 1913, 156, 186-7. [all data]

Landolt and Jahn, 1892
Landolt, H.; Jahn, H., The Molecular Refraction of Several Simple Organic Compounds for Rays of Infinitely Great Wave Length., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1892, 10, 289. [all data]

Notes

Go To: Top, Normal boiling point, References

• Symbols used in this document:
  

  Tboil

  Boiling point

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.