Benzene, 1-methoxy-3-methyl-

Formula: C₈H₁₀O
Molecular weight: 122.1644
IUPAC Standard InChI: InChI=1S/C8H10O/c1-7-4-3-5-8(6-7)9-2/h3-6H,1-2H3
IUPAC Standard InChIKey: OSIGJGFTADMDOB-UHFFFAOYSA-N
CAS Registry Number: 100-84-5
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, m-methyl-; m-Cresol methyl ether; m-Methoxytoluene; m-Methylanisole; Methyl m-tolyl ether; 1-Methoxy-3-methylbenzene; 3-Methoxytoluene; 3-Methylanisole; m-Cresyl methyl ether; Methyl m-cresyl ether; Methyl 3-methylphenyl ether; 1-Methyl-3-methoxybenzene; 3-Methylmethoxybenzene; 3-Methyl-1-methoxybenzene; NSC 6255
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Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
Data at other public NIST sites:
- Gas Phase Kinetics Database
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Gas phase thermochemistry data

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
12.81	100.	Sharma S.N., 1982	Estimations by difference method [ Dorofeeva O.V., 1997] have reason to suppose that Cp(298.15 K) and S(298.15 K) values obtained by [83SHA3] may be underestimated by 10-25 J/mol*K.
23.37	200.
34.152	300.
44.716	400.
53.972	500.
61.671	600.
68.031	700.
73.329	800.
77.780	900.
81.546	1000.
84.751	1100.
87.488	1200.
89.835	1300.
91.855	1400.
93.599	1500.
95.115	1600.
96.432	1700.
97.586	1800.
98.597	1900.
99.491	2000.

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-37.13	kcal/mol	Ccb	Badoche, 1941	Author's hf298_condensed=-40.25 kcal/mol
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1056.86	kcal/mol	Ccb	Badoche, 1941	Author's hf298_condensed=-40.25 kcal/mol; Corresponding Δ_fHº_liquid = -37.12 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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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
T_boil	448.7	K	N/A	Weast and Grasselli, 1989	BS
T_boil	448. to 449.	K	N/A	Frinton Laboratories Inc., 1986	BS
T_boil	449.7	K	N/A	Olson, Hipsher, et al., 1947	Uncertainty assigned by TRC = 0.5 K; TRC
T_boil	449.59	K	N/A	Boord, Greenlee, et al., 1945	Uncertainty assigned by TRC = 0.2 K; TRC
T_boil	449.9	K	N/A	Perkin, 1896	Uncertainty assigned by TRC = 0.5 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	217.23	K	N/A	Olson, Hipsher, et al., 1947	Uncertainty assigned by TRC = 0.4 K; TRC
T_fus	217.9	K	N/A	Boord, Greenlee, et al., 1945	Uncertainty assigned by TRC = 0.3 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	665.3	K	N/A	Young, 1994	Uncertainty assigned by TRC = 0.6 K; TRC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Gas phase ion energetics data

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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
206. ± 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
198. ± 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
8.0	PE	Kobayashi and Nagakura, 1974	LLK
8.4 ± 0.1	EI	Brown, 1970	RDSH
8.31 ± 0.05	EI	Pignataro, Foffani, et al., 1966	RDSH
8.1 ± 0.15	CTS	Voigt and Reid, 1964	RDSH
8.28	PE	Kobayashi and Nagakura, 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₆H₇⁺	12.9	?	EI	Harrison, Haynes, et al., 1965	RDSH
C₇H₇O⁺	11.6 ± 0.1	CH₃	EI	Brown, 1970	RDSH
C₇H₇O⁺	11.3 ± 0.1	CH₃	EI	Tait, Shannon, et al., 1962	RDSH
C₇H₈⁺	11.2 ± 0.1	CH₂O	EI	Brown, 1970	RDSH
C₇H₉⁺	11.7	CO+H?	EI	Harrison, Haynes, et al., 1965	RDSH
C₈H₉O⁺	12.1 ± 0.1	H	EI	Meyer and Harrison, 1964	RDSH

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Notes

Sharma S.N., 1982
Sharma S.N., Infrared and laser Raman spectra of m- and p-methylanisoles, Acta Phys. Pol., 1982, A62, 449-456. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]

Badoche, 1941
Badoche, M., No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE., Bull. Soc. Chim. Fr., 1941, 8, 212-220. [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]

Frinton Laboratories Inc., 1986
Frinton Laboratories Inc., Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [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]

Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted benzenes, Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]

Brown, 1970
Brown, P., Kinetic studies in mass spectrometry. VIII. Competing [M-CH₃] and [M-CH₂O] reactions in substituted anisoles. Approximate activation energies from ionization appearance potentials, Org. Mass Spectrom., 1970, 4, 519. [all data]

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH₂-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [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]

Harrison, Haynes, et al., 1965
Harrison, A.G.; Haynes, P.; McLean, S.; Meyer, F., The mass spectra of methyl-substituted cyclopentadienes, J. Am. Chem. Soc., 1965, 87, 5099. [all data]

Tait, Shannon, et al., 1962
Tait, J.M.S.; Shannon, T.W.; Harrison, A.G., The structure of substituted C₇ ions from benzyl derivatives at the appearance potential threshold, J. Am. Chem. Soc., 1962, 84, 4. [all data]

Meyer and Harrison, 1964
Meyer, F.; Harrison, A.G., An electron impact study of methyl phenyl ethers, Can. J. Chem., 1964, 42, 2008. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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