1-Butanol, 3-methyl-

• Formula: C₅H₁₂O
• Molecular weight: 88.1482
• IUPAC Standard InChI: InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: PHTQWCKDNZKARW-UHFFFAOYSA-N Copy
• CAS Registry Number: 123-51-3
• 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: Isopentyl alcohol; Fermentation amyl alcohol; Fusel Oil; Isoamyl alcohol; Isoamylol; Isobutyl carbinol; Isopentanol; 2-Methyl-4-butanol; 3-Methyl-1-butanol; 3-Methylbutanol; Alcool amilico; Alcool isoamylique; Amylowy alkohol; iso-amylalkohol; 3-Methylbutan-1-ol; 3-Metil-butanolo; Isoamyl alcohol, primary; Butanol, 3-methyl-; Butan-1-ol, 3-methyl; i-Amyl alcohol; Isopentan-1-ol; Methyl-3-butan-1-ol; NSC 1029; UN 1105; 3-methylbutanoI; Isoamyl alcohol (3-methyl butanol)
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• Information on this page:
  • Normal boiling point
  • References
  • Notes
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  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
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Normal boiling point

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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein

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.

Tanaka, Muramatsu, et al., 1992
Tanaka, H.; Muramatsu, T.; Kato, M., Isobaric Vapor-Liquid Equilibria for Three Binary Systems of 2-Butanone with 3-Methyl-1-butanol, 1-Butanol, or 2-Butanol, J. Chem. Eng. Data, 1992, 37, 164. [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]

Markovnik, Shvaro, et al., 1986
Markovnik, V.S.; Shvaro, O.V.; Al'khimovich, V.M.; Sachek, A.I., Temperature dependence of vapor pressure, of heats of formation, combustion, and vaporization of 3-methyl-1-butanol, Termodin. Org. Soedin., 1986, 1986, 68. [all data]

Mouli, Naidu, et al., 1986
Mouli, J.C.; Naidu, P.R.; Choudary, N.V., Excess Volumes, Ultrasonic Sound Velocities, and Isentropic Compress- ibilites of 1-Chlorobutane with Isopropyl, Isobutyl, and Isopentyl Alc isopentyl alcohols, J. Chem. Eng. Data, 1986, 31, 493. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Rao and Reddy, 1985
Rao, K.P.C.; Reddy, K.S. (see subram k), Excess volumes and excess isentropic compressibilities of binary mixtures of N. N. dimethylformamide with branched alcohols at 303.15K, Thermochim. Acta, 1985, 91, 321. [all data]

Karunakar, Reddy, et al., 1982
Karunakar, J.; Reddy, K.D.; Rao, M.V.P., Excess volumes of a homologous series of aliphatic alcohols with benzonitrile, J. Chem. Eng. Data, 1982, 27, 346-7. [all data]

Ravi Prasad, Rao, et al., 1981
Ravi Prasad, A.; Rao, K.V.; Chiranjivi, C., Binary Vqapor-Liquid Equilibria of Iso Alcohol-Tetrachloroethene Systems, J. Chem. Eng. Data, 1981, 26, 211. [all data]

Subba Rao, Rao, et al., 1979
Subba Rao, D.; Rao, K.V.; Ravi Prasad, A.; Chiranjivi, C., J. Chem. Eng. Data, 1979, 24, 241-4. [all data]

Kal'nitskaya, Komarova, et al., 1977
Kal'nitskaya, A.M.; Komarova, L.F.; Garber, Yu.N., Azeotropic Series of aliphatic Alcohols with Acetate Esters, Zh. Prikl. Khim. (Leningrad), 1977, 50, 1101-5. [all data]

Miller and Huang, 1972
Miller, K.J.; Huang, H.-S., Vapor-liquid equilibrium for binary systems 2-butanone with 2-butanol, 1- pentanol, and isoamyl alcohol, J. Chem. Eng. Data, 1972, 17, 77-8. [all data]

Thayumanasundaram and Rao, 1971
Thayumanasundaram, R.; Rao, P.B., Viscosities of Biunary Mixtures of n-Buthyl Acetate-Methyl Ethyl Ketone or Isoamyl Alcohol at 35 deg C, J. Chem. Eng. Data, 1971, 16, 323. [all data]

Ananthanarayanan and Rao, 1968
Ananthanarayanan, P.; Rao, P.B., Ternary Liquid Equilibria of the Water-Phosphoric Acid-Isoamyl Alcohol, Cyclohexanol, or Methyl Isobutyl Ketone Systems at 35 deg C, J. Chem. Eng. Data, 1968, 13, 194-6. [all data]

Reddy and Rao, 1965
Reddy, M.S.; Rao, C.V., Isothermal and Isobaric Vapor-Liquid Equilibrium Data System: Toluene- Isoamyl Alcohol, J. Chem. Eng. Data, 1965, 10, 309. [all data]

Raju, Ranganathan, et al., 1963
Raju, B.N.; Ranganathan, R.; Narasinga Rao, M., Thermodynamics of Vapour-liquid Equilibria System: (1) Benzene-cuene (1) Isoamyl Alochol-cumene (3) Methanol-methylcyclohexane, Indian Chem. Eng., 1963, 5, 82. [all data]

Terry, Kepner, et al., 1960
Terry, T.D.; Kepner, R.E.; Dinsmore, W., Binary Systems Containing Isoamyl Alcohol or Active Amyl Alcohol, J. Chem. Eng. Data, 1960, 5, 403. [all data]

Zieborak and Wyrzykowska-Stankiewicz, 1960
Zieborak, K.; Wyrzykowska-Stankiewicz, D., A new kind of ternary saddle azeotrope, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1960, 8, 137. [all data]

Arnold and Washburn, 1958
Arnold, V.W.; Washburn, E.R., Ternary system isoamyl alcohol + isopropyl alcohol + water at 10, 25 and 40 c, J. Phys. Chem., 1958, 62, 1088. [all data]

Romadane, 1957
Romadane, I., Zh. Obshch. Khim., 1957, 27, 1939. [all data]

Ikeda, Kepner, et al., 1956
Ikeda, R.M.; Kepner, R.E.; Webb, A.D., Densities, refractive indices, and rotations of mixtures of active amyl and isoamyl alcohols application to analysis, Anal. Chem., 1956, 28, 1335-6. [all data]

Kreglewski, 1955
Kreglewski, A., The Critical Temperatures of Mixtures formed by Benzene and n-Octane with Iso-Alcohols, Rocz. Chem., 1955, 29, 754. [all data]

McKenna, Tartar, et al., 1953
McKenna, F.E.; Tartar, H.V.; Lingafelter, E.C., Studies of hemiacetal formation in alcohol - aldehyde systems: II refraction studies, J. Am. Chem. Soc., 1953, 75, 604-7. [all data]

Cook, 1952
Cook, N.C., , Unpublished, Final Rep. Stand. Proj. on Oxygenated Compounds, Penn. State Univ., College Park, PA, 1952. [all data]

Bonauguri, Bicelli, et al., 1951
Bonauguri, E.; Bicelli, L.; Spiller, G., Distillation research: I aromatic hydrocarbons and alcohols, Chim. Ind. (Milan), 1951, 33, 81. [all data]

Pichler, Ziesecke, et al., 1950
Pichler, H.; Ziesecke, K.H.; Traeger, B., The Oxygen-containing Compounds, Especially Alcohols, Formed in Isosynthesis, Brennst.-Chem., 1950, 31, 361. [all data]

Lecat, 1949
Lecat, M., Tables Azeotropiques, Vol. 1, 10th ed., Brussels, Belgium, 1949. [all data]

Leech, 1949
Leech, J.W., The measurement of the specific heats of some organic liquids using the cooling method, Proc. Phys. Soc. London, Sect. B, 1949, 62, 390-8. [all data]

Lecat, 1947
Lecat, M., Orthobaric Azeotropes of Sulfides, Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]

Lecat, 1947, 2
Lecat, M., Some azeotropes of which one constituant is heterocyclic nitrogen, Ann. Soc. Sci. Bruxelles, Ser. 1, 1947, 61, 73. [all data]

Addison, 1945
Addison, C.C., 26. The Properties of Freshly Formed Surfaces. IV. The Influence of Chain Length and Structure on the Static and the Dynamic Surface Tensions of Aqueous Alcoholic Solutions, J. Chem. Soc., 1945, 1945, 98-106. [all data]

Komarewsky and Smith, 1944
Komarewsky, V.I.; Smith, L.G., The Action of Chromia Cat. on Aliphatic Iso-Alcohols and Iso-Aldehydes, J. Am. Chem. Soc., 1944, 66, 1116-7. [all data]

Bohnsack, 1943
Bohnsack, H., Chem. Ber., 1943, 76, 564. [all data]

Bohnsack, 1942
Bohnsack, H., Chem. Ber., 1942, 75, 502. [all data]

Bohnsack, 1942, 2
Bohnsack, H., Chem. Ber., 1942, 75, 72. [all data]

Paul, 1941
Paul, R., Bull. Soc. Chim. Fr., 1941, 8, 507. [all data]

Veibel, Lunquist, et al., 1939
Veibel, S.; Lunquist, F.; Anderson, F.; Frederiksen, E., Bull. Soc. Chim. Fr., 1939, 6, 990. [all data]

Ginnings and Baum, 1937
Ginnings, P.M.; Baum, R., Aqueous Solubilities of the Isomeric Pentanols, J. Am. Chem. Soc., 1937, 59, 1111-1113. [all data]

Tomonari, 1936
Tomonari, T., Optical properties of liquid mixtures of ketones and alcohol, Z. Phys. Chem., Abt. B, 1936, 32, 202-21. [all data]

Coull and Hope, 1935
Coull, J.; Hope, H.B., The ternary system isoamyl alcohol + propyl alcohol + water, J. Phys. Chem., 1935, 39, 967-971. [all data]

Carter and Jones, 1934
Carter, E.G.; Jones, D.C., An experimental test of the validity of antonow's rule, Trans. Faraday Soc., 1934, 30, 1027. [all data]

Kogl and Erxleben, 1934
Kogl, F.; Erxleben, H., Z. Physiol. Chem., 1934, 227, 51. [all data]

Wojcik and Adkins, 1933
Wojcik, B.; Adkins, H., Hydogenolysis of Succinates and Glutarates, J. Am. Chem. Soc., 1933, 55, 4939. [all data]

Dadieu, Pongratz, et al., 1932
Dadieu, A.; Pongratz, A.; Kohlraush, K.W.F., Monatsh. Chem., 1932, 61, 409. [all data]

Longuinov and Pryanishinkov, 1931
Longuinov, V.; Pryanishinkov, A., Tr. Inst. Chist. Khim. Reakt., 1931, No. 12, 18. [all data]

Lecat, 1930
Lecat, M., Azeotropism in Binary Mixtures Containing an Alcohol Mixed with an amine, a nitro derivative, an ether or water., Z. Anorg. Allg. Chem., 1930, 186, 119. [all data]

Senderens and Aboulenc, 1930
Senderens, J.B.; Aboulenc, J., C. R. Hebd. Seances Acad. Sci., 1930, 190, 150. [all data]

Timmermans and Hennaut-Roland, 1929
Timmermans, J.; Hennaut-Roland, M., Isoamyl compounds, An. R. Soc. Esp. Fis. Quim., 1929, 27, 460-72. [all data]

Lloyd, Brown, et al., 1928
Lloyd, E.; Brown, C.B.; Bonnell, D.G.R.; Jones, W.J., Equilibriu9m Between Alcohols and Salts Part II, J. Chem. Soc., 1928, 1928, 658-66. [all data]

Kirkpatrick, 1927
Kirkpatrick, Chem. Metall. Eng., 1927, 34, 276. [all data]

Krchma and Williams, 1927
Krchma, I.J.; Williams, J.W., J. Am. Chem. Soc., 1927, 49, 2408. [all data]

Lecat, 1927
Lecat, M., New binary azeotropes: 7th list, Ann. Soc. Sci. Bruxelles, Ser. B, 1927, 47, 108-14. [all data]

Lecat, 1927, 2
Lecat, M., New binary azeotropes: 5th list, Recl. Trav. Chim. Pays-Bas, 1927, 46, 240-7. [all data]

Norris and Cortese, 1927
Norris, J.F.; Cortese, F., The reactivity of atoms and groups in organic compounds: II. second contribution on the relative reactivities of the hydroxyl-hydrogen atoms in certain alcohols, J. Am. Chem. Soc., 1927, 49, 2640-50. [all data]

Timmermans, 1927
Timmermans, J., The Melting Point of Organic Substances, Bull. Soc. Chim. Belg., 1927, 36, 502. [all data]

Fischer and Schmidt, 1926
Fischer; Schmidt, Chem. Ber., 1926, 59, 679. [all data]

Hannotte, 1926
Hannotte, T., Azeotropic Properties of Formic Ethers and Acetates of Saturated Aliphatic Alcohols, Bull. Soc. Chim. Belg., 1926, 35, 86. [all data]

Lecat, 1926
Lecat, M., New binary azeotropes: 3rd list, Ann. Soc. Sci. Bruxelles, Ser. B, 1926, 45, 284-94. [all data]

Lecat, 1926, 2
Lecat, M., New binary azeotropes second list, Recl. Trav. Chim. Pays-Bas, 1926, 45, 620-627. [all data]

Mathews, 1926
Mathews, J.H., The Accurate Measurement of Heats of Vaporization of Liquids, J. Am. Chem. Soc., 1926, 48, 562. [all data]

Munch, 1926
Munch, J.C., The Refractometric Determination of Alcohols and Esters in Aqueous and in Cottonseed Oil Solutions, J. Am. Chem. Soc., 1926, 48, 994-1003. [all data]

Adams and Adkins, 1925
Adams, E.W.; Adkins, H., Catalysis in Acetal Formation, J. Am. Chem. Soc., 1925, 47, 1358-67. [all data]

Kablukov and Malischeva, 1925
Kablukov, I.A.; Malischeva, V.T., The volumetric method of measurement of the mutual solubility of liquids the mutual solubility of the systems ethyl ether + water and iso-amyl alcohol + water, J. Am. Chem. Soc., 1925, 47, 1553-61. [all data]

Palmer and Constable, 1925
Palmer, W.G.; Constable, F.H., Proc. R. Soc. London, A, 1925, 107, 255. [all data]

Wuyts, 1925
Wuyts, H., C. R. Hebd. Seances Acad. Sci., 1925, 180, 671. [all data]

Williams and Daniels, 1924
Williams, J.W.; Daniels, F., The Specific Heats of Certain Organic Liquids at Elevated Temperatures, J. Am. Chem. Soc., 1924, 46, 903-17. [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]

Popelier, 1923
Popelier, J., Preparation of the ethers of primary alcohols, Bull. Soc. Chim. Belg., 1923, 32, 179-93. [all data]

Cox, 1920
Cox, H.E., J. Chem. Soc., 1920, 117, 493. [all data]

Neuberg and Renjer, 1918
Neuberg, C.; Renjer, Biochem. Z., 1918, 90, 388. [all data]

Willcox and Brunel, 1916
Willcox, M.; Brunel, R.F., J. Am. Chem. Soc., 1916, 38, 1821. [all data]

Vavon, 1914
Vavon, G., Hydrogeneration catalyst in the presence of platinum blacks. Transformation of aldehydes and ketones to alcohols, Ann. Chim. (Paris), 1914, 1, 144-200. [all data]

Timmermans, 1911
Timmermans, J., Researches on the freezing point of organic liquid compounds, Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]

Parnas, 1910
Parnas, J., Biochem. Z., 1910, 28, 274. [all data]

Flaschner, 1909
Flaschner, O., The miscibility of the pyridine bases with water and the influence of a critical-solution point on the shape of the melting-point curve, J. Chem. Soc., 1909, 95, 668. [all data]

Sabatier and Mailhe, 1909
Sabatier, P.; Mailhe, A., New Applications of the General Method of Hydrogenation with Various Metals, Ann. Chim. Phys., 1909, 16, 70. [all data]

Richards and Mathews, 1908
Richards, T.W.; Mathews, J.H., The Relation Between Compressibility, Surface Tension, and Other Properties of Material, J. Am. Chem. Soc., 1908, 30, 8-13. [all data]

Sabatier and Senderens, 1903
Sabatier, P.; Senderens, J.B., C. R. Hebd. Seances Acad. Sci., 1903, 137, 302. [all data]

Young and Fortey, 1902
Young, S.; Fortey, E.C., LXXIV. The Properties of Mixtures of the Lower Alcohols with Water, J. Chem. Soc., 1902, 81, 717. [all data]

Louguinine, 1898
Louguinine, W., Study of Latent Heats of Vaporizaion of Some Liquids, Ann. Chim. Phys., 1898, 13, 289-377. [all data]

Kahlbaum, 1884
Kahlbaum, G.W.A., The dependence of Boiling Temperature on Air Pressure, Ber. Dtsch. Chem. Ges., 1884, 17, 1245. [all data]

Perkin, 1884
Perkin, W.H., On the Magnetic Rotary Polarisation of Compounds in Relation to their Chemical Consitution; with Observations on the Preparation and Relative Densities of the Bodies Examined, J. Chem. Soc., 1884, 45, 421-580. [all data]

Kobig, 1879
Kobig, J., Justus Liebigs Ann. Chem., 1879, 195, 92. [all data]

Pedler, 1868
Pedler, A., J. Chem. Soc., 1868, 21, 74. [all data]

Notes

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• Symbols used in this document:
  

  Tboil

  Boiling point

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