2-Butanol, 3-methyl-
- Formula: C5H12O
- Molecular weight: 88.1482
- IUPAC Standard InChIKey: MXLMTQWGSQIYOW-UHFFFAOYSA-N
- CAS Registry Number: 598-75-4
- 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. - Stereoisomers:
- Other names: sec-Isoamyl alcohol; Methylisopropylcarbinol; 3-Methyl-2-butanol; (CH3)2CHCH(OH)CH3; (.+/-.)-3-Methyl-2-butanol; Butan-2-ol, 3-methyl-; 3-Methyl-butan-2-ol; 1,2-Dimethyl-1-propanol; 1,2-Dimethylpropanol; 2-Methyl-3-butanol; NSC 71162
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Gas phase thermochemistry data
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -75.62 ± 0.43 | kcal/mol | Eqk | Connett, 1970 | ALS |
ΔfH°gas | -74.83 | kcal/mol | N/A | Chao and Rossini, 1965 | Value computed using ΔfHliquid° value of -366.6±0.7 kj/mol from Chao and Rossini, 1965 and ΔvapH° value of 53.5 kj/mol from Connett, 1970.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 92.88 ± 0.91 | cal/mol*K | N/A | Connett, 1970 | This value was obtained from equilibrium study.; GT |
Condensed phase thermochemistry data
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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 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 |
---|---|---|---|---|---|
ΔfH°liquid | -88.41 ± 0.33 | kcal/mol | Eqk | Connett, 1970 | ALS |
ΔfH°liquid | -87.63 ± 0.17 | kcal/mol | Ccb | Chao and Rossini, 1965 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -792.33 ± 0.15 | kcal/mol | Ccb | Chao and Rossini, 1965 | Corresponding ΔfHºliquid = -87.82 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58.77 | 298.15 | Atrashenok, Nesterov, et al., 1991 | T = 218 to 373 K. Cp(liq) = 4.81853 - 3.12708(T/100) + 0.182356(T/100)2 + 0.484126(T/100)3 - 0.0905712(T/100)4 kJ/kg*K.; DH |
Phase change data
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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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 385. ± 3. | K | AVG | N/A | Average of 23 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 131.5 | K | N/A | Zubkov, Peshenko, et al., 1990 | Glass phase; Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 556.1 ± 0.5 | K | N/A | Gude and Teja, 1995 | |
Tc | 556.1 | K | N/A | Quadri, Khilar, et al., 1991 | Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 38.2 ± 0.2 | atm | N/A | Gude and Teja, 1995 | |
Pc | 38.19 | atm | N/A | Quadri, Khilar, et al., 1991 | Uncertainty assigned by TRC = 0.39 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12.67 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 12.3 ± 0.07 | kcal/mol | GS | Kulikov, Verevkin, et al., 2001 | Based on data from 280. to 301. K.; AC |
ΔvapH° | 12.8 ± 0.1 | kcal/mol | V | Connett, 1970 | ALS |
ΔvapH° | 12.4 | kcal/mol | C | McCurdy and Laidler, 1963 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.7 | 295. | A | Stephenson and Malanowski, 1987 | Based on data from 280. to 375. K.; AC |
11.1 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 293. to 385. K.; AC |
12.6 | 313. | N/A | Wilhoit and Zwolinski, 1973 | Based on data from 298. to 384. K.; AC |
Reaction thermochemistry data
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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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C5H11O- + =
By formula: C5H11O- + H+ = C5H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 372.7 ± 2.0 | kcal/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
ΔrH° | 373.0 ± 2.8 | kcal/mol | G+TS | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 366.1 ± 2.1 | kcal/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
ΔrG° | 366.4 ± 2.7 | kcal/mol | CIDC | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: C5H12O = H2 + C5H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.9 ± 0.38 | kcal/mol | Eqk | Connett, 1970 | gas phase; ALS |
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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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 | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Connett, 1970
Connett, J.E.,
Chemical equilibria. Part III. Dehydrogenation of pentan-1-ol, pentan-2-ol, and 3-methylbutan-2-ol,
J. Chem. Soc. A, 1970, 1284-1286. [all data]
Chao and Rossini, 1965
Chao, J.; Rossini, F.D.,
Heats of combustion, formation, and isomerization of nineteen alkanols,
J. Chem. Eng. Data, 1965, 10, 374-379. [all data]
Atrashenok, Nesterov, et al., 1991
Atrashenok, T.R.; Nesterov, N.A.; Zhuk, I.P.; Peshchenko, A.D.,
Measured specific heats of hexan-1-ol and 3-methyl-2-butanol over wide temperature ranges,
Inzh.-Fiz. Zh., 1991, 61(2), 301-304. [all data]
Zubkov, Peshenko, et al., 1990
Zubkov, V.I.; Peshenko, A.D.; Markovnik, V.S.,
Thermodynamic properties of 3-methyl-2-butanol and 3,3-dimethyl-2-butanol
in Vses. Konf. Term. Org. Soedin. 6th, Minsk, p 46, 1990. [all data]
Gude and Teja, 1995
Gude, M.; Teja, A.S.,
Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols,
J. Chem. Eng. Data, 1995, 40, 1025-1036. [all data]
Quadri, Khilar, et al., 1991
Quadri, S.K.; Khilar, K.C.; Kudchadker, A.P.; Patni, M.J.,
Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable alkanols,
J. Chem. Thermodyn., 1991, 23, 67-76. [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]
Kulikov, Verevkin, et al., 2001
Kulikov, Dmitry; Verevkin, Sergey P.; Heintz, Andreas,
Determination of Vapor Pressures and Vaporization Enthalpies of the Aliphatic Branched C 5 and C 6 Alcohols,
J. Chem. Eng. Data, 2001, 46, 6, 1593-1600, https://doi.org/10.1021/je010187p
. [all data]
McCurdy and Laidler, 1963
McCurdy, K.G.; Laidler, K.J.,
HEATS OF VAPORIZATION OF A SERIES OF ALIPHATIC ALCOHOLS,
Can. J. Chem., 1963, 41, 8, 1867-1871, https://doi.org/10.1139/v63-274
. [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]
Wilhoit and Zwolinski, 1973
Wilhoit, R.C.; Zwolinski, B.J.,
Physical and thermodynamic properties of aliphatic alcohols,
J. Phys. Chem. Ref. Data Suppl., 1973, 1, 2, 1. [all data]
Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G.,
The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols,
Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W
. [all data]
Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T.,
The gas phase acidity of aliphatic alcohols,
J. Am. Chem. Soc., 1983, 105, 2203. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°gas Entropy of gas at standard conditions Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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