Phenol, o-amino-

• Formula: C₆H₇NO
• Molecular weight: 109.1259
• IUPAC Standard InChI: InChI=1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2 Copy

  
• IUPAC Standard InChIKey: CDAWCLOXVUBKRW-UHFFFAOYSA-N Copy
• CAS Registry Number: 95-55-6
• 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: o-Hydroxyaniline; Phenol, 2-amino-; o-Aminophenol; o-Hydroxyphenylamine; Benzofur GG; BASF Ursol 3GA; C.I. Oxidation Base 17; C.I. 76520; Fouramine OP; Nako Yellow 3GA; Paradone Olive Green B; Pelagol Grey GG; Pelagol 3GA; Zoba 3GA; 1-Amino-2-hydroxybenzene; 1-Hydroxy-2-aminobenzene; 2-Aminophenol; 2-Hydroxyaniline; Benzene, 1-hydroxy-2-amine-; Nako Yellow ga; 2-Amino-1-hydroxybenzene; 2-Hydroxyanaline; Questiomycin B; 2-Aminophenyl alcohol; NSC 1534
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess

View reactions leading to C₆H₇NO⁺ (ion structure unspecified)

De-protonation reactions

C₆H₆NO^- +  =

By formula: C₆H₆NO^- + H⁺ = C₆H₇NO

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, custom temperature program

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References

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

Bret-Dibat and Lichanot, 1989
Bret-Dibat, P.; Lichanot, A., Proprietes thermodynamiques des isomeres de position de benzenes disubstitues en phase condensee, Thermochim. Acta, 1989, 147, 2, 261, https://doi.org/10.1016/0040-6031(89)85181-0 . [all data]

Kemula, Buchowski, et al., 1968
Kemula, W.; Buchowski, H.; Pawlowski, W., Effect of the position of substituents in an aromatic ring on R(f) and partition coefficients: II. aromatic amines, Rocz. Chem., 1968, 42, 1951. [all data]

Sabbah and Gouali, 1996
Sabbah, R.; Gouali, M., Energetique des liaisons inter et intramoleculaires dans les trois isomeres de l'aminophenol, Can. J. Chem., 1996, 74, 500-507. [all data]

Nunez, Barral, et al., 1986
Nunez, L.; Barral, L.; Largo, S.G.; Pilcher, G., Enthalpies of combustion of the three aminophenols, J. Chem. Thermodyn., 1986, 18, 575-579. [all data]

Huang, 2003
Huang, C.-Y., , M.S. Thesis, Chinese Culture University, 2003. [all data]

Huang, Tang, et al., 2005
Huang, Chih-Yung; Tang, Muoi; Chen, Yan-Ping, Solid-Liquid Equilibria for 3-Aminophenol + 2-Aminophenol, 4-(Acetylamino)toluene + 2-(Acetylamino)toluene, and 3,4,5-Trimethoxybenzoic Acid + 2,4,5-Trimethoxybenzoic Acid, J. Chem. Eng. Data, 2005, 50, 1, 40-43, https://doi.org/10.1021/je049878m . [all data]

Rotich, Glass, et al., 2001
Rotich, M.K.; Glass, B.D.; Brown, M.E., Journal of Thermal Analysis and Calorimetry, 2001, 64, 2, 681-688, https://doi.org/10.1023/A:1011584125859 . [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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]

Dolecka, Raczynska, et al., 1988
Dolecka, E.; Raczynska, E.D.; Drapala, T., Retention indices and basicity of N¹N¹-dimethyl-N²-phenylformamidines ortho-substituent effect, J. Chem. Soc. Perkin Trans. 2:, 1988, 3, 257-260, https://doi.org/10.1039/p29880000257 . [all data]

Grzybowski, Lamparczyk, et al., 1980
Grzybowski, J.; Lamparczyk, H.; Nasal, A.; Radecki, A., Relationship between the retention indices of phenols on polar and non-polar stationary phases, J. Chromatogr., 1980, 196, 2, 217-223, https://doi.org/10.1016/S0021-9673(00)80441-0 . [all data]

Peterson, 1992
Peterson, K.L., Counter-Propagation Neural Networks in the Modeling and Prediction of Kovats Indices for Substituted Phenols, Anal. Chem., 1992, 64, 4, 379-386, https://doi.org/10.1021/ac00028a011 . [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

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