Phenol, 2,6-dichloro-
- Formula: C6H4Cl2O
- Molecular weight: 163.001
- IUPAC Standard InChIKey: HOLHYSJJBXSLMV-UHFFFAOYSA-N
- CAS Registry Number: 87-65-0
- 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: 2,6-Dichlorophenol; 2,6-Dichlorfenol; Rcra waste number U082
- Permanent link for this species. Use this link for bookmarking this species for future reference.
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
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 | -34.97 ± 0.36 | kcal/mol | Ccr | Ribeiro Da Silva, Ferrao, et al., 1994 | HCl (1:600 H2O) |
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 | -53.08 ± 0.26 | kcal/mol | Ccr | Ribeiro Da Silva, Ferrao, et al., 1994 | HCl (1:600 H2O) |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -659.2 ± 0.2 | kcal/mol | Ccr | Ribeiro Da Silva, Ferrao, et al., 1994 | HCl (1:600 H2O) |
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 492.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 340.0 | K | N/A | Poeti, Faneli, et al., 1982 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14.2 ± 0.07 | kcal/mol | GS | Verevkin, Emel'yanenko, et al., 2007 | Based on data from 341. to 371. K.; AC |
ΔvapH° | 14.0 ± 0.1 | kcal/mol | N/A | Mokbel, Pauchon, et al., 1995 | Based on data from 343. to 457. K. See also Verevkin, Emel'yanenko, et al., 2007.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 19.0 ± 0.05 | kcal/mol | GS | Verevkin, Emel'yanenko, et al., 2007 | Based on data from 299. to 331. K.; AC |
ΔsubH° | 18.1 ± 0.24 | kcal/mol | C | Ribeiro Da Silva, Ferrao, et al., 1994 | HCl (1:600 H2O); ALS |
ΔsubH° | 18.1 ± 0.26 | kcal/mol | C | da Silva, 1994 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
355.7 | 0.005 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.2 | 356. | GS | Verevkin, Emel'yanenko, et al., 2007 | Based on data from 341. to 371. K.; AC |
12.3 | 400. | N/A | Mokbel, Pauchon, et al., 1995 | Based on data from 343. to 457. K. See also Verevkin, Emel'yanenko, et al., 2007.; AC |
13.8 | 348. | A | Stephenson and Malanowski, 1987 | Based on data from 333. to 493. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
332.7 to 493. | 5.32242 | 2431.802 | -36.391 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.2918 | 340.0 | Poeti, Fanelli, et al., 1982 | DH |
5.292 | 340. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.56 | 340.0 | Poeti, Fanelli, et al., 1982 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
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 C6H4Cl2O+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference |
---|---|---|
8.65 ± 0.02 | PE | Maier and Turner, 1973 |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, References, Notes
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
View image of digitized spectrum (can be printed in landscape orientation).
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, 1992 |
NIST MS number | 125471 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-30 | 160. | 1200. | Evans and Haken, 1989 | Column length: 25. m; Column diameter: 0.32 mm |
Capillary | SE-30 | 180. | 1194. | Shakirov, Tsypysheva, et al., 1988 | Column length: 20. m; Column diameter: 0.2 mm |
Capillary | SE-30 | 140. | 1189. | Korhonen, 1984 | |
Capillary | SE-30 | 160. | 1200. | Korhonen, 1984 | |
Capillary | SE-30 | 180. | 1214. | Korhonen, 1984 | |
Packed | Methyl Silicone | 150. | 1203. | Radecki, Grzybowski, et al., 1979 |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1206. | Grzybowski, Lamparczyk, et al., 1980 | Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | FFAP | 160. | 2097. | Evans and Haken, 1989 | Column length: 25. m; Column diameter: 0.35 mm |
Capillary | FFAP | 160. | 2097. | Korhonen, 1984 | |
Capillary | FFAP | 180. | 2081. | Korhonen, 1984 | |
Capillary | FFAP | 200. | 2083. | Korhonen, 1984 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1205. | Gocmen, Elston, et al., 2005 | 60. m/0.25 mm/0.25 μm, 7. K/min; Tstart: 40. C; Tend: 275. C |
Capillary | DB-5 | 1213. | Gocmen, Elston, et al., 2005 | 60. m/0.25 mm/0.25 μm, 7. K/min; Tstart: 40. C; Tend: 275. C |
Capillary | SE-30 | 1198. | Korhonen, 1984 | 10. K/min; Tstart: 100. C |
Capillary | SE-30 | 1179. | Korhonen, 1984 | 2. K/min; Tstart: 100. C |
Capillary | SE-30 | 1190. | Korhonen, 1984 | 6. K/min; Tstart: 100. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 1223.2 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Capillary | 5 % Phenyl methyl siloxane | 1199. | Yasuhara, Shiraishi, et al., 1997 | 25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 2119. | Gocmen, Elston, et al., 2005 | 30. m/0.32 mm/0.5 μm, 7. K/min, 240. C @ 5. min; Tstart: 40. C |
Capillary | DB-Wax | 2124. | Gocmen, Elston, et al., 2005 | 30. m/0.32 mm/0.5 μm, 7. K/min, 240. C @ 5. min; Tstart: 40. C |
Capillary | FFAP | 2061. | Korhonen, 1984 | 10. K/min; Tstart: 100. C |
Capillary | FFAP | 2038. | Korhonen, 1984 | 6. K/min; Tstart: 100. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 1149. | Messadi and Ali-Mokhnache, 1993 | 2. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 80. C |
Capillary | OV-101 | 1151. | Messadi and Ali-Mokhnache, 1993 | 2. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 80. C |
Capillary | OV-101 | 1178. | Messadi and Ali-Mokhnache, 1993 | 2. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 80. C |
Capillary | OV-101 | 1179. | Messadi and Ali-Mokhnache, 1993 | 2. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 80. C |
Capillary | Ultra-1 | 1168. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1189. | Yu and Zazhi, 2005 | Program: not specified |
Capillary | PTE-5 | 1227. | Nakano, Fujimori, et al., 1992 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min) |
Capillary | Ultra-2 | 1228. | Nakano, Fujimori, et al., 1992 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min) |
Capillary | SE-30 | 1206. | Peterson, 1992 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 204.68 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C |
Capillary | DB-5MS | 203.40 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 4. K/min; Tend: 310. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Ribeiro Da Silva, Ferrao, et al., 1994
Ribeiro Da Silva, M.A.V.; Ferrao, M.L.C.C.H.; Jiye, F.,
Standard enthalpies of combustion of the six dichlorophenols by rotating-bomb calorimetry,
J. Chem. Thermodyn., 1994, 26, 839-846. [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]
Poeti, Faneli, et al., 1982
Poeti, G.; Faneli, E.; Braghetti, M.J.,
A differential scanning calorimetric study of some phenol derivatives,
Therm. Anal., 1982, 24, 2, 273, https://doi.org/10.1007/BF01913681
. [all data]
Verevkin, Emel'yanenko, et al., 2007
Verevkin, Sergey P.; Emel'yanenko, Vladimir N.; Klamt, Andreas,
Thermochemistry of Chlorobenzenes and Chlorophenols: Ambient Temperature Vapor Pressures and Enthalpies of Phase Transitions,
J. Chem. Eng. Data, 2007, 52, 2, 499-510, https://doi.org/10.1021/je060429r
. [all data]
Mokbel, Pauchon, et al., 1995
Mokbel, I.; Pauchon, V.; Jose, J.,
Vapor pressures and sublimation pressures of 2,4-dichlorophenol, 2,6-dichlorophenol, and 2,4,6-trichlorophenol,
ELDATA: Int. Electron. J. Phys. Chem. Data, 1995, 1, 1, 53. [all data]
da Silva, 1994
da Silva, M.,
Standard enthalpies of combustion of the six dichlorophenols by rotating-bomb calorimetry,
The Journal of Chemical Thermodynamics, 1994, 26, 8, 839-846, https://doi.org/10.1006/jcht.1994.1100
. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Poeti, Fanelli, et al., 1982
Poeti, G.; Fanelli, E.; Braghetti, M.,
A differential scanning calorimetric study of some phenol derivatives,
J. Therm. Anal., 1982, 24(2), 273-279. [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]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]
Evans and Haken, 1989
Evans, M.B.; Haken, J.K.,
Dispersion and selectivity indices in gas chromatography. IV. Chlorinated aromatic compounds,
J. Chromatogr., 1989, 468, 373-382, https://doi.org/10.1016/S0021-9673(00)96332-5
. [all data]
Shakirov, Tsypysheva, et al., 1988
Shakirov, L.G.; Tsypysheva, L.G.; Suleimamova, R.A.; Naimushin, A.I.; Tsypyshev, O.Yu.,
Gas chromatographic determination of the products of the synthesis of chlorine-substituted salicylic acids,
Zh. Anal. Khim., 1988, 43, 143-146. [all data]
Korhonen, 1984
Korhonen, I.O.O.,
Gas-liquid chromatographic analyses. XXXI. Retention increments of isomeric chlorophenols on low-polarity (SE-30) and polar (FFAP) capillary columns,
J. Chromatogr., 1984, 315, 185-200, https://doi.org/10.1016/S0021-9673(01)90736-8
. [all data]
Radecki, Grzybowski, et al., 1979
Radecki, A.; Grzybowski, J.; Lamparczyk, H.; Nasal, A.,
Relationships between retention indices and substituent constants of phenols on polar stationary phases,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1979, 2, 9, 581-582, https://doi.org/10.1002/jhrc.1240020911
. [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]
Gocmen, Elston, et al., 2005
Gocmen, D.; Elston, A.; Williams, T.; Parish, M.; Rouseff, R.L.,
Identification of medicinal off-flavours generated by Alicyclobacillus species in orange juice using GC-olfactometry and GC-MS,
Lett. Appl. Microbiol., 2005, 40, 3, 172-177, https://doi.org/10.1111/j.1472-765X.2004.01636.x
. [all data]
Tret'yakov, 2007
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]
Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y.,
Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry,
J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2
. [all data]
Messadi and Ali-Mokhnache, 1993
Messadi, D.; Ali-Mokhnache, S.,
Calculation of retention indices and peak widths in temperature programmed gas-liquid chromatography,
Chromatographia, 1993, 37, 5/6, 264-270, https://doi.org/10.1007/BF02278631
. [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]
Yu and Zazhi, 2005
Yu, H.; Zazhi, J.,
Relationship between chromatogram retention index and toxicity of chlorinated phenols and chlorinated benzenes to Guppy,
J. Enviropn. Health (Chinese), 2005, 22, 6, 441-444. [all data]
Nakano, Fujimori, et al., 1992
Nakano, T.; Fujimori, K.; Takaishi, Y.; Okuno, T.,
GC/MS-SIM analysis of polychlorobenzenes, polychlorophenols and polychloronaphthalenes,
Report of the Environmental Science Institute of Hyogo Prefecture, 1992, 24, 30-37. [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]
Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W.,
Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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 ΔfusS Entropy of fusion ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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