Phenol, 2-(1-methylethyl)-
- Formula: C9H12O
- Molecular weight: 136.1910
- IUPAC Standard InChI: InChI=1S/C9H12O/c1-7(2)8-5-3-4-6-9(8)10/h3-7,10H,1-2H3
- IUPAC Standard InChIKey: CRBJBYGJVIBWIY-UHFFFAOYSA-N
- CAS Registry Number: 88-69-7
- 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: Phenol, o-isopropyl-; o-Isopropylphenol; 2-Isopropylphenol; 2-(1-Methylethyl)phenol; o-Cumenol; Isopropylphenol, ortho; 1-Hydroxy-2-isopropylbenzene; Prodox 131; o-Hydroxycumene; NSC 5103
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Gas phase ion energetics data
Go To: Top, IR Spectrum, 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: John E. Bartmess
View reactions leading to C9H12O+ (ion structure unspecified)
De-protonation reactions
C9H11O- + =
By formula: C9H11O- + H+ = C9H12O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1454. ± 9.2 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1423. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale |
IR 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.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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| Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | Sadtler Research Labs Under US-EPA Contract |
| State | gas |
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, IR Spectrum, 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).
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| 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 | Japan AIST/NIMC Database- Spectrum MS-NW-5377 |
| NIST MS number | 229164 |
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
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | SE-30 | 100. | 1178. | Berezkin, Popova, et al., 1997 | 30. m/0.25 mm/0.5 μm, He |
| Capillary | PS-255 | 150. | 1175. | Engewald, Billing, et al., 1988 | 50. m/0.30 mm/0.25 μm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | 5 % Phenyl methyl siloxane | 1184. | Climent and Miranda, 1996 | He, 80. C @ 3. min, 20. K/min, 300. C @ 0. min; Column length: 25. m |
| Capillary | OV-1 | 1175.4 | Gautzsch and Zinn, 1996 | 8. K/min; Tstart: 35. C; Tend: 300. C |
| Capillary | DB-5 | 1203. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5MS | 1198.9 | Mjøs, Meier, et al., 2006 | 50. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 30C/min => 100C => 1C/min => |
| Capillary | VF-5MS | 1199.2 | Mjøs, Meier, et al., 2006 | 50. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 30C/min => 100C => 2C/min => |
| Capillary | VF-5MS | 1200.2 | Mjøs, Meier, et al., 2006 | 50. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 30C/min => 100C => 4C/min => |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | BP-1 | 1175. | Health Safety Executive, 2000 | 50. m/0.22 mm/0.75 μm, He, 5. K/min; Tstart: 50. C; Tend: 200. C |
| Capillary | Ultra-1 | 1173. | 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 | HP-5 | 1200. | Zhao, Li, et al., 2008 | 30. m/0.25 mm/0.25 μm; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min) |
| Capillary | HP-5 | 1198. | Zhao, Li, et al., 2008 | 30. m/0.25 mm/0.25 μm; Program: not specified |
| Capillary | SE-30 | 1200. | Vinogradov, 2004 | Program: not specified |
| Capillary | DB-1 | 1175. | Peng, 1996 | 30. m/0.53 mm/1.5 μm; Program: 40 0C (4 min) 8 0C/min -> 200 0C (1 min) 5 0C/min -> 280 0C (20 min) |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-FFAP | 2111. | Czerny, Brueckner, et al., 2011 | 30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 8. K/min, 230. C @ 5. min |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 2089. | Peng, 1996 | 30. m/0.53 mm/1.0 μm; Program: 40 0C (4 min) 4 0C/min -> 200 0C (20 min) |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 203.41 | 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 ion energetics data, IR Spectrum, 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.
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Berezkin, Popova, et al., 1997
Berezkin, V.G.; Popova, T.P.; Shiryayeva, V.Ye.; Nomura, N.,
Gas-chromatographic separation of monoalkylphenols on polar and non-polar phases by means of capillary chromatography,
Pet. Chem. USSR (Engl. Transl.), 1997, 37, 2, 161-167. [all data]
Engewald, Billing, et al., 1988
Engewald, W.; Billing, U.; Topalova, I.; Petsev, N.,
Structure-retention correlations of alkylphenols in gas-liquid and gas-solid chromatography,
J. Chromatogr., 1988, 446, 71-77, https://doi.org/10.1016/S0021-9673(00)94419-4
. [all data]
Climent and Miranda, 1996
Climent, M.J.; Miranda, M.A.,
Gas chromatographic - mass spectrometric study of photodegradation of carbamate pesticides,
J. Chromatogr. A, 1996, 738, 2, 225-231, https://doi.org/10.1016/0021-9673(96)00084-2
. [all data]
Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P.,
Use of incremental models to estimate the retention indexes of aromatic compounds,
Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946
. [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]
Mjøs, Meier, et al., 2006
Mjøs, S.A.; Meier, S.; Boitsov, S.,
Alkylphenol retention indices,
J. Chromatogr. A, 2006, 1123, 1, 98-105, https://doi.org/10.1016/j.chroma.2006.05.002
. [all data]
Health Safety Executive, 2000
Health Safety Executive,
MDHS 96 Volatile organic compounds in air - Laboratory method using pumed solid sorbent tubes, solvent desorption and gas chromatography
in Methods for the Determination of Hazardous Substances (MDHS) guidance, Crown, Colegate, Norwich, 2000, 1-24, retrieved from http://www.hse.gov.uk/pubns/mdhs/pdfs/mdhs96.pdf. [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]
Zhao, Li, et al., 2008
Zhao, Y.; Li, J.; Xu, Y.; Duan, H.; Fan, W.; Zhao, G.,
EXtraction, preparation and identification of volatile compounds in Changyu XO brandy,
Chinese J. Chromatogr., 2008, 26, 2, 212-222, https://doi.org/10.1016/S1872-2059(08)60014-0
. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Peng, 1996
Peng, C.T.,
Gas chromatographic identification of aromatic hydrocarbons
in Liquid Scintillation Spectrometry, Cook, G.T.; Harkness, D.D.; MacKenzie, A.B.; Miller, B.F.; Scott, E.M., ed(s)., 1996, 221-232. [all data]
Czerny, Brueckner, et al., 2011
Czerny, M.; Brueckner, R.; Kirchoff, E.; Schmitt, R.; Buettner, A.,
The influence of molecular structure on odor qualities and odor detection thresholds of volatile alkylated phenols,
Chem. Senses, 2011, 1-15, retrieved from http://chemie.oxfordjournals.org. [all data]
Notes
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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