o-Hydroxybiphenyl
- Formula: C12H10O
- Molecular weight: 170.2072
- IUPAC Standard InChIKey: LLEMOWNGBBNAJR-UHFFFAOYSA-N
- CAS Registry Number: 90-43-7
- 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: [1,1'-Biphenyl]-2-ol; 2-Biphenylol; o-Biphenylol; o-Diphenylol; o-Hydroxydiphenyl; o-Phenylphenol; o-Xenol; Biphenyl-2-ol; Dowicide 1; Phenol, o-phenyl-; 2-Phenylphenol; Preventol O extra; Remol TRF; 2-Hydroxybiphenyl; 2-Hydroxydiphenyl; o-Phenylphenol, cosmetic grade; Biphenyl, 2-hydroxy-; NCI-C50351; Torsite; Tumescal OPE; USAF EK-2219; 1-Hydroxy-2-phenylbenzene; 2-Hydroxybifenyl; Dowicide 1 antimicrobial; 2-Fenylfenol; Kiwi lustr 277; OPP; Orthohydroxydiphenyl; Orthophenylphenol; Orthoxenol; Tetrosin OE; Nectryl; Anthrapole 73; 2-Hydroxy-1,1'-biphenyl; Invalon OP; Tetrosin OE-N; (1,1-Biphenyl)-2-ol; Hydroxy-2-phenylbenzene; Nipacide OPP; Phenylphenol; Phenylphenol (ortho-); NSC 1548; Preventol 3041
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 17. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -88. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -6063. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | Corresponding ΔfHºsolid = -88. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 261.75 | J/mol*K | N/A | Geidarov, Dzhafarov, et al., 1973 | DH |
S°solid,1 bar | 261.75 | J/mol*K | N/A | Geidarov, Karasharli, et al., 1977 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
227.61 | 298.15 | Geidarov, Karasharli, et al., 1977 | Based on previously published work of authors, not available in detail, on Cp 12 to 370 K.; DH |
235.10 | 298.15 | Geidarov, Dzhafarov, et al., 1973 | T = 12 to 350 K. Complete Cp data in paper deposited at VINITI, No. 4748-72, 24 Aug, 1972.; DH |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 555.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 548. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 331.20 | K | N/A | Donnelly, Drewes, et al., 1990 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 329. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 330. | K | N/A | Gilman and Esmay, 1953 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 330.6 | K | N/A | Geidarov, Karasharli, et al., 1977, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 88.5 ± 0.9 | kJ/mol | GS | Verevkin, 1998 | AC |
ΔsubH° | 104.3 | kJ/mol | C | Bertholon, Giray, et al., 1971 | ALS |
ΔsubH° | 105.0 | kJ/mol | N/A | Bertholon, Giray, et al., 1971 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
418.2 | 0.019 | Weast and Grasselli, 1989 | BS |
418. | 0.019 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
94.2 | 449. | A | Stephenson and Malanowski, 1987 | Based on data from 434. to 547. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
435.1 to 548. | 2.11107 | 540.999 | -297.156 | von Terres, Gebert, et al., 1955 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
87.6 ± 0.9 | 314. | GS | Verevkin, 1998 | Based on data from 301. to 328. K.; AC |
82.9 | 303. | N/A | Stephenson and Malanowski, 1987 | Based on data from 292. to 314. K. See also Aihara, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
16.213 | 330.6 | N/A | Geidarov, Dzhafarov, et al., 1973 | DH |
16.213 | 330.60 | N/A | Geidarov, Karasharli, et al., 1977 | DH |
15.48 | 333.7 | DSC | Verevkin, 1998 | AC |
16.21 | 330.6 | N/A | Geidarov, Dzhafarov, et al., 1973 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
49.04 | 330.6 | Geidarov, Dzhafarov, et al., 1973 | DH |
49.04 | 330.60 | Geidarov, Karasharli, et al., 1977 | DH |
49.03 | 330.6 | Geidarov, Dzhafarov, et al., 1973 | CAL |
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 compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C12H10O+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference |
---|---|---|
7.80 ± 0.02 | PE | Maier and Turner, 1972 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Source | Bol'shakov, et al., 1969 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 20216 |
Instrument | unknown |
Melting point | 59 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bertholon, Giray, et al., 1971
Bertholon, G.; Giray, M.; Perrin, R.; Vincent-Falquet-Berny, M.F.,
No. 532. - Etude physicochimique des phenols. OX. - Ethanlpies de combustion et energies de resonance des alcoyl et aryphenols,
Bull. Soc. Chim. France, 1971, 3180-3187. [all data]
Geidarov, Dzhafarov, et al., 1973
Geidarov, Kh.I.; Dzhafarov, O.I.; Karasharli, K.A.; Kostryukov, V.N.,
Thermodynamics of o-hydroxybiphenyl at low temperatures,
Zhur. Fiz. Khim., 1973, 47, 275. [all data]
Geidarov, Karasharli, et al., 1977
Geidarov, Kh.I.; Karasharli, K.A.; Dzhafarov, O.I.,
Analysis of the results of the thermodynamic investigation of diphenyl derivatives,
Azerb. Khim. Zhur., 1977, (5), 112-115. [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]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Donnelly, Drewes, et al., 1990
Donnelly, J.R.; Drewes, L.A.; Johnson, R.L.; Munslow, W.D.; Knapp, K.K.; Sovocool, G.W.,
Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry,
Thermochim. Acta, 1990, 167, 2, 155, https://doi.org/10.1016/0040-6031(90)80476-F
. [all data]
Gilman and Esmay, 1953
Gilman, H.; Esmay, E.L.,
The Cleavage of Heterocycles with Raney Nickel and with Lithium,
J. Am. Chem. Soc., 1953, 75, 2947. [all data]
Geidarov, Karasharli, et al., 1977, 2
Geidarov, K.I.; Karasharli, K.A.; Dzhafarov, O.I.,
Analysis of the results of the thermodynamic investigation of diphenyl devivatives,
Azerb. Khim. Zh., 1977, 1977, 112-5. [all data]
Verevkin, 1998
Verevkin, Sergey P.,
Thermochemistry of phenols: experimental standard molar enthalpies of formation of 2-phenylphenol, 4-phenylphenol, 2,6-diphenylphenol, and 2,2´- and 4,4´-dihydroxybiphenyl,
The Journal of Chemical Thermodynamics, 1998, 30, 3, 389-396, https://doi.org/10.1006/jcht.1997.0316
. [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 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]
von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten,
Brennst.-Chem., 1955, 36, 272-274. [all data]
Aihara, 1960
Aihara, Ariyuki,
Estimation of the Energy of Hydrogen Bonds Formed in Crystals. II. Phenols,
Bull. Chem. Soc. Jpn., 1960, 33, 2, 194-200, https://doi.org/10.1246/bcsj.33.194
. [all data]
Maier and Turner, 1972
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part I. Biphenyls,
Faraday Discuss. Chem. Soc., 1972, 54, 149. [all data]
Bol'shakov, et al., 1969
Bol'shakov, G.F., et al.,
Ultraviolet spectra of heteroorganic compounds, 1969, 243. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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