Phenol, 2,4,6-trimethyl-

Formula: C₉H₁₂O
Molecular weight: 136.1910
IUPAC Standard InChI: InChI=1S/C9H12O/c1-6-4-7(2)9(10)8(3)5-6/h4-5,10H,1-3H3
IUPAC Standard InChIKey: BPRYUXCVCCNUFE-UHFFFAOYSA-N
CAS Registry Number: 527-60-6
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Mesitol; Mesityl alcohol; 1-Hydroxy-2,4,6-trimethylbenzene; 2-Hydroxymesitylene; 2,4,6-Trimethylphenol; 2,4,6-Trimetylofenol
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-63.03	kcal/mol	N/A	Khodzhaeva, Iskhakova, et al., 1991	Value computed using Δ_fH_solid° value of -356.8 kj/mol from Khodzhaeva, Iskhakova, et al., 1991 and Δ_subH° value of 93.1 kj/mol from Bertholon, Giray, et al., 1971.; DRB
Δ_fH°_gas	-42.29	kcal/mol	Ccb	Bertholon, Giray, et al., 1971	ALS

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°_solid			Ccb	Khodzhaeva, Iskhakova, et al., 1991	uncertain value: -85.287 kcal/mol; Undetermined error; ALS
Δ_fH°_solid	-65.	kcal/mol	Ccb	Bertholon, Giray, et al., 1971	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid			Ccb	Khodzhaeva, Iskhakova, et al., 1991	uncertain value: -117. ± 15. kcal/mol; Undetermined error; ALS
Δ_cH°_solid	-1191.	kcal/mol	Ccb	Bertholon, Giray, et al., 1971	Corresponding Δ_fHº_solid = -65. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	51.417	cal/mol*K	N/A	Khodzhaeva, Iskhakova, et al., 1991	DH

Constant pressure heat capacity of solid

C_p,solid (cal/mol*K)	Temperature (K)	Reference	Comment
50.937	298.15	Khodzhaeva, Iskhakova, et al., 1991	T = 90 to 320 K. Cp(c) = -460.08(T/100)-2 + 1250.90(T/100)-1 - 1258.35 + 682.09(T/100) - 138.79(T/100)2 + 11.79(T/100)3 J/mol*K.; 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	493.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS
T_boil	494.15	K	N/A	Hey, 1961	Uncertainty assigned by TRC = 3. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	344. ± 3.	K	AVG	N/A	Average of 10 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	19.8 ± 0.07	kcal/mol	GS	Verevkin, 1999	AC
Δ_subH°	22.7	kcal/mol	C	Bertholon, Giray, et al., 1971, 2	See also Verevkin, 1999.; AC
Δ_subH°	22.71	kcal/mol	C	Bertholon, Giray, et al., 1971	ALS
Δ_subH°	22.3	kcal/mol	N/A	Bertholon, Giray, et al., 1971	DRB

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
12.7	382.	A	Stephenson and Malanowski, 1987	Based on data from 367. to 494. K. See also von Terres, Gebert, et al., 1955.; 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
367. to 493.8	4.50984	1917.363	-68.384	von Terres, Gebert, et al., 1955, 2	Coefficents calculated by NIST from author's data.

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:

References

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

Khodzhaeva, Iskhakova, et al., 1991
Khodzhaeva, M.G.; Iskhakova, B.G.; Abdusalyamov, N.N.; Ismailov, T.S., Heat capacity and thermodynamics of 2,4,6-trimethylphenol, Uzb. Khim. Zh., 1991, 27-29. [all data]

Bertholon, Giray, et al., 1971
Bertholon, G.; Giray, M.; Perrin, R.; Vincent-Falquet-Berny, M.F., No. 532. - Etude physicochimique des phenols. OX. - Ethanlpies de combustion et energies de resonance des alcoyl et aryphenols, Bull. Soc. Chim. France, 1971, 3180-3187. [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]

Hey, 1961
Hey, D.H., J. Chem. Soc., 1961, 1961, 1581. [all data]

Verevkin, 1999
Verevkin, Sergey P., Thermochemistry of phenols: buttress effects in sterically hindered phenols, The Journal of Chemical Thermodynamics, 1999, 31, 11, 1397-1416, https://doi.org/10.1006/jcht.1999.0466 . [all data]

Bertholon, Giray, et al., 1971, 2
Bertholon, G.; Giray, M.; Perrin, R.; Vincent-Falquet-Berny, M.F., Bull. Soc. Chim. Fr., 1971, 9, 3180. [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]

von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W., Brennst.-Chem., 1955, 36, 272. [all data]

von Terres, Gebert, et al., 1955, 2
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W., Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten, Brennst.-Chem., 1955, 36, 272-274. [all data]

Notes

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Symbols used in this document:

C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH	Enthalpy of vaporization

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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