8-Hydroxyquinoline
- Formula: C9H7NO
- Molecular weight: 145.1580
- IUPAC Standard InChI: InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
- IUPAC Standard InChIKey: MCJGNVYPOGVAJF-UHFFFAOYSA-N
- CAS Registry Number: 148-24-3
- 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: Oxyquinoline; 8-Quinolinol; Bioquin; Oxin; Oxine; Oxychinolin; Phenopyridine; Quinophenol; Tumex; 1-Azanaphthalene-8-ol; 8-Hydroxychinolin; 8-Oxyquinoline; 8-OQ; 8-Quinol; Hydroxybenzopyridine; Oxybenzopyridine; Oxychinoline; 8-Oxyquinolin; Fennosan H 30; NCI-C55298; USAF EK-794; 8-Chinolinol; Fennosan; o-Oxychinolin; 8-Quinolol; Oxoquinoline; Quinolin-8-ol; NSC 2039; NSC 615011; NSC 82404
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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 | 6.5 ± 1.7 | kJ/mol | Ccb | Ribeiro Da Silva, Monte, et al., 1989 | Author was aware that data differs from previously reported values |
| ΔfH°gas | 27.6 ± 2.6 | kJ/mol | Ccr | Sakiyama, Nakano, et al., 1975 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -83.0 ± 1.5 | kJ/mol | Ccb | Ribeiro Da Silva, Monte, et al., 1989 | Author was aware that data differs from previously reported values |
| ΔfH°solid | -81.2 ± 2.0 | kJ/mol | Ccr | Sakiyama, Nakano, et al., 1975 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -4459.0 ± 0.9 | kJ/mol | Ccb | Ribeiro Da Silva, Monte, et al., 1989 | Author was aware that data differs from previously reported values |
| ΔcH°solid | -4460.8 ± 1.6 | kJ/mol | Ccr | Sakiyama, Nakano, et al., 1975 | |
| ΔcH°solid | -4467.7 | kJ/mol | Ccb | Wood and Jones, 1963 | |
| ΔcH°solid | -4455.5 ± 0.8 | kJ/mol | Ccb | Sullivan and Hunt, 1949 | |
| ΔcH°solid | -4457.2 ± 8.4 | kJ/mol | Ccb | Sullivan, Kibler, et al., 1948 |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 347.65 | K | N/A | Manske, Ledingham, et al., 1949 | Uncertainty assigned by TRC = 2. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 96. ± 20. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 540.2 | 1.00 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 108.8 ± 1.7 | 308. to 328. | ME | Horton and Wendlandt, 1963 | See also Cox and Pilcher, 1970 and Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 40.3 | 345.7 | AC | WANG, TAN, et al., 2008 | AC |
| 22.1 | 346.8 | N/A | Zorel, Costalonga, et al., 2001 | AC |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLID (SPLIT MULL); PERKIN-ELMER 521 (GRATING); 2 cm-1 resolution
- SOLUTION (10% CCl4 FOR 3800-1320, 10% CS2 FOR 1320-400); BECKMAN IR-9 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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
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Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | NIST Mass Spectrometry Data Center, 1998. |
| NIST MS number | 290917 |
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 | Lang (editor), 1961 |
|---|---|
| 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. 19765 |
| Instrument | SF-4 |
| Melting point | 74 |
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
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 1326.3 | Ferchichi and Messadi, 1994 | 4. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 30. C; Tend: 250. C |
| Capillary | OV-101 | 1348.9 | Ferchichi and Messadi, 1994 | 4. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 30. C; Tend: 250. C |
| Capillary | DB-5 | 1358. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Ultra-1 | 1339. | Du, Clery, et al., 2008 | 50. m/0.20 mm/0.33 μm, Helium, 2. K/min, 280. C @ 20. min; Tstart: 50. C |
| Capillary | HP-5 | 1362. | Du, Clery, et al., 2008 | 50. m/0.20 mm/0.33 μm, Helium, 10. K/min, 280. C @ 8.5 min; Tstart: 50. C |
| Capillary | Ultra-1 | 1312. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-Innowax | 2153. | Du, Clery, et al., 2008 | 50. m/0.20 mm/0.33 μm, Helium, 10. K/min, 250. C @ 6. min; Tstart: 50. C |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 232.24 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Ribeiro Da Silva, Monte, et al., 1989
Ribeiro Da Silva, M.A.V.; Monte, M.J.S.; Matos, M.A.R.,
Enthalpies of combustion, vapour pressures, and enthalpies of sublimation of 8-hydroxyquinoline, 5-nitro-8-hydroxyquinoline, and 2-methyl-8-hydroxyquinoline,
J. Chem. Thermodyn., 1989, 21, 159-166. [all data]
Sakiyama, Nakano, et al., 1975
Sakiyama, M.; Nakano, T.; Seki, S.,
Enthalpies of combustion of organic compounds. I. 8-Quinolinol.,
Bull. Chem. Soc. Jpn., 1975, 48, 1705-1708. [all data]
Wood and Jones, 1963
Wood, J.L.; Jones, M.M.,
Heats of formation and coordinate bond energies of some nickel(II) chelates,
J. Phys. Chem., 1963, 67, 1049-1051. [all data]
Sullivan and Hunt, 1949
Sullivan, M.V.; Hunt, H.,
Heats of combustion. IV. The heats of combustion of five aromatic amines,
J. Phys. Chem., 1949, 53, 497-500. [all data]
Sullivan, Kibler, et al., 1948
Sullivan, M.V.; Kibler, G.M.; Hunt, H.,
Heats of combustion of nitrogen containing compounds, Rpt. Tech. Memo. PUR-3 for USN Project SQUID Contract N6ori-104, Task Order No. 1 Designation No. NR 22 042 by Purdue University, Lafayette, IN, 1948, 1-46. [all data]
Manske, Ledingham, et al., 1949
Manske, R.H.F.; Ledingham, A.E.; Ashford, W.R.,
The preparation of quinolins by a modified Skraup reaction.,
Can. J. Res., 1949, 27F, 359. [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]
Horton and Wendlandt, 1963
Horton, G.R.; Wendlandt, W.W.,
The heats of dissociation of the 8-quinolinol and substituted 8-quinolinol metal chelates of uranium (VI), thorium (IV) and scandium (III),
J. Inorg. Nucl. Chem., 1963, 25, 241-245. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]
WANG, TAN, et al., 2008
WANG, Shao-Xu; TAN, Zhi-Cheng; LI, Yan-Sheng; TONG, Bo; LI, Ying; SHI, Quan; ZHANG, Jing-Nan,
Thermodynamic Study of 8-Hydroxyquinoline by Adiabatic Calorimetry and Thermal Analysis,
Chin. J. Chem., 2008, 26, 11, 2016-2020, https://doi.org/10.1002/cjoc.200890360
. [all data]
Zorel, Costalonga, et al., 2001
Zorel, H.E., Jr.; Costalonga, A.G.C.; Crespi, M.S.; Ribiero, C.A.,
Quim. Nova, 2001, 24, 5, 599. [all data]
Lang (editor), 1961
Lang (editor), L.,
Absorption Spectra in the Ultraviolet and Visible Region, 1961, 2, 373. [all data]
Ferchichi and Messadi, 1994
Ferchichi, L.; Messadi, D.,
Simulations de la rétention et de l'effecacité de colonne en chromatographie en phase gazeuse à température programmée: théorie et application,
Analusis, 1994, 22, 392-399. [all data]
Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E.,
Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603
. [all data]
Du, Clery, et al., 2008
Du, Z.; Clery, R.; Hammond, C.J.,
Volatile organic nitrogen-containing constituents in ambrette seed Abelmoschus moschatus Medik (Malvaceae),
J. Agric. Food Chem., 2008, 56, 16, 7388-7392, https://doi.org/10.1021/jf800958d
. [all data]
Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point 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 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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