Benzene, 1-methoxy-2-methyl-
- Formula: C8H10O
- Molecular weight: 122.1644
- IUPAC Standard InChIKey: DTFKRVXLBCAIOZ-UHFFFAOYSA-N
- CAS Registry Number: 578-58-5
- 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: Anisole, o-methyl-; o-Cresol methyl ether; o-Cresyl methyl ether; o-Methoxytoluene; o-Methylanisole; Methyl o-cresyl ether; Methyl o-tolyl ether; 1-Methoxy-2-methylbenzene; 2-Methoxytoluene; 2-Methylanisole; 2-Methylmethoxybenzene; Methyl o-methylphenyl ether; Methyl-o-cresol; o-Methylanisol; NSC 6253
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Phase change data
Go To: Top, 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 444.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 445.0 | K | N/A | Olson, Hipsher, et al., 1947 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 444.88 | K | N/A | Boord, Greenlee, et al., 1945 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tboil | 557.35 | K | N/A | Perkin, 1896 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 239.05 | K | N/A | Olson, Hipsher, et al., 1947 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 238.97 | K | N/A | Boord, Greenlee, et al., 1945 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 662.0 | K | N/A | Young, 1994 | Uncertainty assigned by TRC = 0.6 K; TRC |
Gas phase ion energetics data
Go To: Top, 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 as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C8H10O+ (ion structure unspecified)
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
203. ± 2. | van Beelen, Koblenz, et al., 2004 | T = 298K; PA derived by authors from GB with protonation entropy equated to Rlnσ(B)/σ(BH+); MM |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
196. ± 2. | van Beelen, Koblenz, et al., 2004 | T = 298K; PA derived by authors from GB with protonation entropy equated to Rlnσ(B)/σ(BH+); MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.90 | PE | Behan, Dean, et al., 1976 | LLK |
8.03 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
8.1 ± 0.15 | CTS | Voigt and Reid, 1964 | RDSH |
8.24 | PE | Friege and Klessinger, 1979 | Vertical value; LLK |
8.24 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
Mass spectrum (electron ionization)
Go To: Top, 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
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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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118456 |
Gas Chromatography
Go To: Top, 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 |
---|---|---|---|---|---|
Packed | Apiezon L | 100. | 1005. | Bogoslovsky, Anvaer, et al., 1978 | Chromatone N AW DNCS |
Packed | Apiezon L | 150. | 1021. | Bogoslovsky, Anvaer, et al., 1978 | Chromatone N AW DNCS |
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 1007. | Siani, Ramos, et al., 1999 | 30. m/0.32 mm/0.25 μm, He, 70. C @ 5. min, 3. K/min; Tend: 250. C |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | Apiezon M | 1013.5 | Jalali-Heravi and Garkani-Nejad, 1993 | Chromosorb W; Column length: 2. m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1013. | Baccouri, Ben Temime, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 240. C |
Capillary | HP-5 | 1013. | Flamini, Tebano, et al., 2006 | 30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; Tend: 220. C |
Capillary | 5 % Phenyl methyl siloxane | 1032. | Estevez, Ventanas, et al., 2005 | 30. m/0.25 mm/1. μm, He, 40. C @ 10. min, 7. K/min, 250. C @ 5. min |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1009. | Priestap, van Baren, et al., 2003 | 30. m/0.2 mm/0.25 μm, He, 75. C @ 4. min, 3. K/min; Tend: 220. C |
Capillary | RSL-200 | 1001. | Jirovetz, Smith, et al., 2002 | 30. m/0.25 mm/0.25 μm, H2, 40. C @ 2. min, 6. K/min, 280. C @ 10. min |
Capillary | DB-1 | 983. | Guy and Vernin, 1996 | He, 70. C @ 5. min, 3. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 300. C |
Capillary | OV-1 | 986. | Wahab, Aboutabl, et al., 1987 | 60. m/0.50 mm/1.2 μm, Helium, 2. K/min; Tstart: 40. C; Tend: 220. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1005. | Hamm, Bleton, et al., 2005 | 30. m/0.25 mm/0.25 μm, He; Program: 40C(1min) => 9C/min => 130C => 2C/min => 230C |
Capillary | BPX-5 | 1009. | Koutsoudaki, Krsek, et al., 2005 | 30. m/0.32 mm/0.5 μm, He; Program: 60C(1min) => 3.5C/min => 180C => 20C/min => 280C(2min) |
Capillary | DB-5 | 1005. | Hamm, Bleton, et al., 2004 | 30. m/0.25 mm/0.25 μm, He; Program: 40C(1min) => 9C/min => 130C => 2C/min => 230C |
Capillary | SE-30 | 1000. | Vinogradov, 2004 | Program: not specified |
Capillary | DB-5 | 1005. | Hamm, Lesellier, et al., 2003 | 30. m/0.25 mm/0.25 μm, He; Program: 40C (1min) => 9C/min => 130C => 2C/min => 230C |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1409. | Priestap, van Baren, et al., 2003 | 50. m/0.25 mm/0.25 μm, N2, 3. K/min; Tstart: 90. C; Tend: 220. C |
Capillary | Carbowax 20M | 1390. | Buttery, Maddox, et al., 1986 | He, 60. C @ 40. min, 1. K/min; Column length: 150. m; Column diameter: 0.66 mm; Tend: 170. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1432. | Vinogradov, 2004 | Program: not specified |
Capillary | Innowax FSC | 1424. | Baser, Demirci, et al., 2003 | 60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C |
References
Go To: Top, 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.
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]
Olson, Hipsher, et al., 1947
Olson, W.T.; Hipsher, H.F.; Buess, C.M.; Goodman, I.A.; Hart, I.; Lamneck, J.H.; Gibbons, L.C.,
The Synthesis and Purification of Ethers,
J. Am. Chem. Soc., 1947, 69, 2451-4. [all data]
Boord, Greenlee, et al., 1945
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L.,
, Am. Pet. Inst. Res. Proj. 45, Seventh Annu. Rep., Ohio State Univ., June 30, 1945. [all data]
Perkin, 1896
Perkin, W.H.,
LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds,
J. Chem. Soc., 1896, 69, 1025-1257. [all data]
Young, 1994
Young, C.L.,
Personal Commun. 1994 1994, 1994. [all data]
van Beelen, Koblenz, et al., 2004
van Beelen, E.S.E.; Koblenz, T.A.; Ingemann, S.; Hammerum, S.,
Experimental and theoretical evaluation of proton affinities of furan, the methylphenols, and the related anisoles,
J. Phys. Chem. A, 2004, 108, 2787. [all data]
Behan, Dean, et al., 1976
Behan, J.M.; Dean, F.M.; Johnstone, R.A.W.,
Photoelectron spectra of cyclic aromatic ethers. The question of the Mills-Nixon effect,
Tetrahedron, 1976, 32, 167. [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]
Voigt and Reid, 1964
Voigt, E.M.; Reid, C.,
Ionization potentials of substituted benzenes and their charge-transfer spectra with tetracyanoethylene,
J. Am. Chem. Soc., 1964, 86, 3930. [all data]
Friege and Klessinger, 1979
Friege, H.; Klessinger, M.,
Elektronenstruktur von Alkyl-aryl- und Alkyl-vinyl-ethern,
Chem. Ber., 1979, 112, 1614. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S.,
Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]
Siani, Ramos, et al., 1999
Siani, A.C.; Ramos, M.F.S.; Menezes-de-Lima, O., Jr.; Ribeiro-dos-Santos, R.; Fernadez-Ferreira, E.; Soares, R.O.A.; Rosas, E.C.; Susunaga, G.S.; Guimarães, A.C.; Zoghbi, M.G.B.; Henriques, M.G.M.O.,
Evaluation of anti-inflammatory-related activity of essential oils from the leaves and resin of species of Protium,
J. Ethnopharmacol., 1999, 66, 1, 57-69, https://doi.org/10.1016/S0378-8741(98)00148-2
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Jalali-Heravi and Garkani-Nejad, 1993
Jalali-Heravi, M.; Garkani-Nejad, Z.,
Prediction of gas chromatographic retention indices of some benzene derivatives,
J. Chromatogr., 1993, 648, 2, 389-393, https://doi.org/10.1016/0021-9673(93)80421-4
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Baccouri, Ben Temime, et al., 2007
Baccouri, B.; Ben Temime, S.; Campeol, E.; Cioni, P.L.; Daoud, D.; Zarrouk, M.,
Application of solid-phase microextraction to the analysis of volatile compounds in virgin olive oils from five new cultivars,
Food Chem., 2007, 102, 3, 850-856, https://doi.org/10.1016/j.foodchem.2006.06.012
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Flamini, Tebano, et al., 2006
Flamini, G.; Tebano, M.; Cioni, P.L.; Bagci, Y.; Dural, H.; Ertugrul, K.; Uysal, T.; Savran, A.,
A multivariate statistical approach to Centaurea classification using essential oil composition data of some species from Turkey,
Pl. Syst. Evol., 2006, 261, 1-4, 217-228, https://doi.org/10.1007/s00606-006-0448-3
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Estevez, Ventanas, et al., 2005
Estevez, M.; Ventanas, S.; Ramirez, R.; Cava, R.,
Influence of the Addition of Rosemary Essential Oil on the Volatiles Pattern of Porcine Frankfurters,
J. Agric. Food Chem., 2005, 53, 21, 8317-8324, https://doi.org/10.1021/jf051025q
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Priestap, van Baren, et al., 2003
Priestap, H.A.; van Baren, C.M.; Lira, P.D.L.; Coussio, J.D.; Bandoni, A.L.,
Volatile constituents of Aristolochia argentina,
Phytochemistry, 2003, 63, 2, 221-225, https://doi.org/10.1016/S0031-9422(02)00751-3
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Jirovetz, Smith, et al., 2002
Jirovetz, L.; Smith, D.; Buchbauer, G.,
Aroma compound analysis of Eruca sativa (Brassicaceae) SPME headspace leaf samples using GC, GC-MS, and olfactometry,
J. Agric. Food Chem., 2002, 50, 16, 4643-4646, https://doi.org/10.1021/jf020129n
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Guy and Vernin, 1996
Guy, I.; Vernin, G.,
Minor compounds from Cistus ladaniferus L. essential oil from esterel. 2. Acids and phenols,
J. Essent. Oil Res., 1996, 8, 4, 455-462, https://doi.org/10.1080/10412905.1996.9700666
. [all data]
Wahab, Aboutabl, et al., 1987
Wahab, S.M.A.; Aboutabl, E.A.; El-Zalabani, S.M.; DePooter, H.L.; Al-Fallaha, B.,
The essential oil of olibanum,
Planta Medica, 1987, 53, 04, 382-384, https://doi.org/10.1055/s-2006-962745
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Hamm, Bleton, et al., 2005
Hamm, S.; Bleton, J.; Connan, J.; Tchapla, A.,
A chemical investigation by headspace SPME and GC-MS of volatile and semi-volatile terpenes in various olibanum samples,
Phytochemistry, 2005, 66, 12, 1499-1514, https://doi.org/10.1016/j.phytochem.2005.04.025
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Koutsoudaki, Krsek, et al., 2005
Koutsoudaki, C.; Krsek, M.; Rodger, A.,
Chemical composition and antibacterial activity of the essential oil and the gum of pistacia lentiscus Var. chia,
J. Agric. Food Chem., 2005, 53, 20, 7681-7685, https://doi.org/10.1021/jf050639s
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Hamm, Bleton, et al., 2004
Hamm, S.; Bleton, J.; Tchapla, A.,
Headspace solid phase microextraction for screening for the presence of resins in Egyptian archaeological samples,
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Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Hamm, Lesellier, et al., 2003
Hamm, S.; Lesellier, E.; Bleton, J.; Tchapla, A.,
Optimization of headspace solid phase microextraction for gas chromatography/mass spectrometry analysis of widely different volatility and polarity terpenoids in olibanum,
J. Chromatogr. A, 2003, 1018, 1, 73-83, https://doi.org/10.1016/j.chroma.2003.08.027
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Buttery, Maddox, et al., 1986
Buttery, R.G.; Maddox, D.M.; Light, D.M.; Ling, L.C.,
Volatile components of yellow starthistle,
J. Agric. Food Chem., 1986, 34, 5, 786-788, https://doi.org/10.1021/jf00071a004
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Baser, Demirci, et al., 2003
Baser, K.H.C.; Demirci, B.; Dekebo, A.; Dagne, E.,
Essential oils of some Boswellia spp., myrrh and opopanax,
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Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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