Benzene, ethoxy-

Formula: C₈H₁₀O
Molecular weight: 122.1644
IUPAC Standard InChI: InChI=1S/C8H10O/c1-2-9-8-6-4-3-5-7-8/h3-7H,2H2,1H3
IUPAC Standard InChIKey: DLRJIFUOBPOJNS-UHFFFAOYSA-N
CAS Registry Number: 103-73-1
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: Phenetole; Ethoxybenzene; Ethyl phenyl ether; Phenyl ethyl ether; Ether, ethyl phenyl-; Phenoxyethane; Benzyl methyl ether
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Other data available:
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- Gas Phase Kinetics Database
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Condensed phase thermochemistry data

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Data compiled as indicated in comments:
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
Δ_fH°_liquid	-36.48 ± 0.28	kcal/mol	Ccb	Fenwick, Harrop, et al., 1975	Author was aware that data differs from previously reported values; ALS
Δ_fH°_liquid	-38.10	kcal/mol	Ccb	Badoche, 1941	Author's hf298-condensed=-41.22 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1057.50	kcal/mol	Ccb	Fenwick, Harrop, et al., 1975	Author was aware that data differs from previously reported values; Corresponding Δ_fHº_liquid = -36.482 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1055.89	kcal/mol	Ccb	Badoche, 1941	Author's hf298-condensed=-41.22 kcal/mol; Corresponding Δ_fHº_liquid = -38.09 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
54.61	298.15	Fenwick, Harrop, et al., 1975, 2	DH

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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity	Value	Units	Method	Reference	Comment
T_boil	443.4 ± 0.4	K	AVG	N/A	Average of 11 out of 12 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	243.63	K	N/A	Dreisbach and Martin, 1949	Uncertainty assigned by TRC = 0.05 K; TRC
T_fus	243.68	K	N/A	Olson, Hipsher, et al., 1947	Uncertainty assigned by TRC = 0.3 K; TRC
T_fus	243.48	K	N/A	Boord, Greenlee, et al., 1945	Uncertainty assigned by TRC = 0.3 K; TRC
T_fus	242.95	K	N/A	Timmermans, 1921	Uncertainty assigned by TRC = 0.3 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	647.0	K	N/A	Guye and Mallet, 1902	Uncertainty assigned by TRC = 2. K; TRC
T_c	647.15	K	N/A	Guye and Mallet, 1902, 2	Uncertainty assigned by TRC = 2.5 K; accompanied by some decomposition; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	33.75	atm	N/A	Guye and Mallet, 1902	Uncertainty assigned by TRC = 0.8000 atm; TRC
P_c	33.9000	atm	N/A	Guye and Mallet, 1902, 2	Uncertainty assigned by TRC = 0.99995 atm; TRC
P_c	33.7000	atm	N/A	Guye and Mallet, 1902, 2	Uncertainty assigned by TRC = 0.99995 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	12.20	kcal/mol	N/A	Majer and Svoboda, 1985
Δ_vapH°	12.1	kcal/mol	N/A	Ambrose, Ellender, et al., 1976	Based on data from 390. to 454. K.; AC
Δ_vapH°	12.20 ± 0.029	kcal/mol	C	Fenwick, Harrop, et al., 1975	Author was aware that data differs from previously reported values; ALS
Δ_vapH°	12.2	kcal/mol	N/A	Fenwick, Harrop, et al., 1975	DRB
Δ_vapH°	12.2 ± 0.02	kcal/mol	C	Fenwick, Harrop, et al., 1975	AC

Reduced pressure boiling point

T_boil (K)	Pressure (atm)	Reference	Comment
333.2	0.01	Weast and Grasselli, 1989	BS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
10.6	405.	A	Stephenson and Malanowski, 1987	Based on data from 390. to 454. K. See also Ambrose, Ellender, et al., 1976.; AC
9.73	443.	N/A	Ambrose, Ellender, et al., 1976	Based on data from 390. to 454. K.; AC
10.5	415.	N/A	Collerson, Counsell, et al., 1965	Based on data from 400. to 454. K. See also Boublik, Fried, et al., 1984.; 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
390.58 to 453.8	4.1390	1507.267	-78.793	Collerson, Counsell, et al., 1965, 2

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:
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)

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.6	EI	Williams, Cooks, et al., 1968	RDSH
8.13 ± 0.02	PI	Watanabe, Nakayama, et al., 1962	RDSH
8.36	PE	Friege and Klessinger, 1979	Vertical value; LLK
8.41	PE	Dewar, Ernstbrunner, et al., 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₆H₆O⁺	10.03 ± 0.19	C₂H₄	EI	Bouchoux, 1978	LLK
C₆H₆O⁺	11.3	C₂H₄	EI	Williams, Cooks, et al., 1968	RDSH
C₆H₆O⁺	10.73	C₂H₄	EI	Gillis, Long, et al., 1968	RDSH

References

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

Fenwick, Harrop, et al., 1975
Fenwick, J.O.; Harrop, D.; Head, A.J., Thermodynamic properties of organic oxygen compounds. 41. Enthalpies of formation of eight ethers, J. Chem. Thermodyn., 1975, 7, 943-954. [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]

Fenwick, Harrop, et al., 1975, 2
Fenwick, J.O.; Harrop, D.; Head, A.J., Thermodynamic properties of organic oxygen compounds. 41. Enthalpies of formation of eight ethers, J. Chem. Thermodynam., 1975, 7, 944-954. [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 2875-8. [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]

Timmermans, 1921
Timmermans, J., The Freezing Points of Organic Substances IV. New Exp. Determinations, Bull. Soc. Chim. Belg., 1921, 30, 62. [all data]

Guye and Mallet, 1902
Guye, P.A.; Mallet, E., Critical Constant and Molecular Complexity of Several Organic Compds., C. R. Hebd. Seances Acad. Sci., 1902, 133, 168. [all data]

Guye and Mallet, 1902, 2
Guye, P.A.; Mallet, E., Measurement of Critical Constants, Arch. Sci. Phys. Nat., 1902, 13, 274-296. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Ambrose, Ellender, et al., 1976
Ambrose, D.; Ellender, J.H.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XLIII. Vapour pressures of some ethers, The Journal of Chemical Thermodynamics, 1976, 8, 2, 165-178, https://doi.org/10.1016/0021-9614(76)90090-2 . [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]

Collerson, Counsell, et al., 1965
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S., 677. Thermodynamic properties of organic oxygen compounds. Part XV. Purification and vapour pressures of some ketones and ethers, J. Chem. Soc., 1965, 3697, https://doi.org/10.1039/jr9650003697 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Collerson, Counsell, et al., 1965, 2
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S., Thermodynamic Properties of Organic Oxygen Compounds. Part XV. Purification and Vapour Pressures of Some Ketones and Ethers, J. Chem. Soc., 1965, 3697-3700, https://doi.org/10.1039/jr9650003697 . [all data]

Williams, Cooks, et al., 1968
Williams, D.H.; Cooks, R.G.; Howe, I., Studies in mass spectrometry. XXXI. A comparison of reaction rates in common ions generated via fragmentation and direct ionization, J. Am. Chem. Soc., 1968, 90, 6759. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]

Dewar, Ernstbrunner, et al., 1974
Dewar, P.S.; Ernstbrunner, E.; Gilmore, J.R.; Godfrey, M.; Mellor, J.M., Conformational analysis of alkyl aryl ethers and alkyl aryl sulphides by photoelectron spectroscopy, Tetrahedron, 1974, 30, 2455. [all data]

Bouchoux, 1978
Bouchoux, G., Ionisation et fragmentation en spectrometrie de masse, Org. Mass Spectrom., 1978, 13, 184. [all data]

Gillis, Long, et al., 1968
Gillis, R.G.; Long, G.J.; Moritz, A.G.; Occolowitz, J.L., Energetics of the electron-impact fragmentation of alkoxybenzenes and alkylthiobenzenes, Org. Mass Spectrom., 1968, 1, 527. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,liquid	Constant pressure heat capacity of liquid
P_c	Critical pressure
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
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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