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 ion energetics data
Go To: Top, IR Spectrum, 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:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
View reactions leading to C5H12O+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.75 ± 0.05 | EI | George and Holmes, 1990 | LL |
10.01 ± 0.07 | EI | Bowen and Maccoll, 1984 | LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4O+ | 10.1 ± 0.1 | C3H8 | EI | George and Holmes, 1990 | LL |
C2H5O+ | 10.1 ± 0.05 | C3H7 | EI | George and Holmes, 1990 | LL |
C2H5O+ | 10.09 | 2-C3H7 | EI | Holmes, Lossing, et al., 1988 | LL |
C4H8O+ | 10.0 ± 0.1 | CH4 | EI | George and Holmes, 1990 | LL |
C4H9O+ | 9.90 ± 0.05 | CH3 | EI | George and Holmes, 1990 | LL |
De-protonation reactions
C5H11O- + =
By formula: C5H11O- + H+ = C5H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1559. ± 8.4 | kJ/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
ΔrH° | 1561. ± 12. | kJ/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° | 1532. ± 8.8 | kJ/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
ΔrG° | 1533. ± 11. | kJ/mol | CIDC | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
IR Spectrum
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 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 |
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, IR Spectrum, 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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | Japan AIST/NIMC Database- Spectrum MS-NW-1316 |
NIST MS number | 233629 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, IR Spectrum, 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 |
---|---|---|---|---|---|
Capillary | SE-30 | 100. | 683. | Tarjan, Nyiredy, et al., 1989 | |
Capillary | SE-30 | 60. | 683. | Tarjan, Nyiredy, et al., 1989 | |
Capillary | SE-30 | 80. | 668. | Tarjan, Nyiredy, et al., 1989 | |
Capillary | SE-30 | 100. | 683. | Haken and Korhonen, 1985 | Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 120. | 690. | Haken and Korhonen, 1985 | Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 140. | 699. | Haken and Korhonen, 1985 | Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 60. | 683. | Haken and Korhonen, 1985 | Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 80. | 668. | Haken and Korhonen, 1985 | Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 100. | 683. | Haken, Madden, et al., 1985 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 120. | 690. | Haken, Madden, et al., 1985 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 140. | 699. | Haken, Madden, et al., 1985 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 60. | 683. | Haken, Madden, et al., 1985 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 80. | 668. | Haken, Madden, et al., 1985 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Packed | SE-30 | 150. | 670. | Tiess, 1984 | Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m |
Packed | Apiezon L | 120. | 652. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 656. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | SE-30 | 100. | 672. | Zarazir, Chovin, et al., 1970 | Chromosorb W; Column length: 2. m |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-351 | 100. | 1108. | Haken and Korhonen, 1985 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Capillary | OV-351 | 60. | 1100. | Haken and Korhonen, 1985 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Capillary | OV-351 | 80. | 1094. | Haken and Korhonen, 1985 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Capillary | OV-351 | 100. | 1108. | Haken, Madden, et al., 1985 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Capillary | OV-351 | 60. | 1100. | Haken, Madden, et al., 1985 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Capillary | OV-351 | 80. | 1094. | Haken, Madden, et al., 1985 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Packed | Carbowax 20M | 100. | 1090. | Zarazir, Chovin, et al., 1970 | Chromosorb W; Column length: 2. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 663. | Korhonen, 1984 | 6. K/min; Column length: 25. m; Column diameter: 0.3 mm; Tstart: 50. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 692.1 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CP-Wax 52CB | 1124. | Liu, Yang, et al., 2001 | H2, 2. K/min; Column length: 50. m; Column diameter: 0.32 mm; Tstart: 50. C; Tend: 200. C |
Capillary | OV-351 | 1079. | Korhonen, 1984 | 6. K/min; Column length: 25. m; Column diameter: 0.32 mm; Tstart: 50. C |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1094. | Bianchi, Careri, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min) |
Capillary | FFAP | 1118. | Yasuhara, 1987 | 50. m/0.25 mm/0.25 μm, He; Program: 20C (5min) => 2C/min => 70C => 4C/min => 210C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 664. | Rapior, Breheret, et al., 1997 | 30. m/0.2 mm/0.25 μm, He, 50. C @ 2. min, 4. K/min; Tend: 200. C |
Capillary | HP-5 | 700. | Larsen and Frisvad, 1995 | 35. C @ 2. min, 6. K/min; Tend: 200. C |
Capillary | OV-101 | 671. | Anker, Jurs, et al., 1990 | 2. K/min; Column length: 50. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
Capillary | OV-101 | 675. | del Rosario, de Lumen, et al., 1984 | He, 0. C @ 1. min, 3. K/min; Column length: 50. m; Column diameter: 0.31 mm; Tend: 225. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 666. | Feng and Mu, 2007 | Program: not specified |
Capillary | SE-30 | 671. | Vinogradov, 2004 | Program: not specified |
Capillary | Polydimethyl siloxane | 666. | Junkes, Castanho, et al., 2003 | Program: not specified |
Capillary | Methyl Silicone | 666. | Estrada and Gutierrez, 1999 | Program: not specified |
Capillary | Polydimethyl siloxanes | 675. | Zenkevich, 1998 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 646. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 663. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | TC-Wax | 1083. | Suhardi, Suzuki, et al., 2002 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 10. min, 3. K/min, 230. C @ 10. min |
Capillary | DB-Wax | 1089. | Parada, Duque, et al., 2000 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min |
Capillary | DB-Wax | 1100. | Pollak and Berger, 1996 | 30. m/0.32 mm/0.5 μm, He, 40. C @ 1. min, 3. K/min, 210. C @ 25. min |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-Innowax | 1089. | Narain, Galvao, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 30C(5min) => 7C/min => 100C(5min) => 1C/min => 130C => 10C/min => 195C(45min) |
Capillary | HP-Innowax | 1091. | Narain, Galvao, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 30C(5min) => 7C/min => 100C(5min) => 1C/min => 130C => 10C/min => 195C(45min) |
References
Go To: Top, Gas phase ion energetics data, IR Spectrum, 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.
George and Holmes, 1990
George, M.; Holmes, J.L.,
Intermediate ion structures in the fragmentation of metastable 3-methylbutan-2-ol radical cations,
Org. Mass Spectrom., 1990, 25, 605. [all data]
Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A.,
Low energy, low temperature mass spectra,
Org. Mass Spectrom., 1984, 19, 379. [all data]
Holmes, Lossing, et al., 1988
Holmes, J.L.; Lossing, F.P.; Maccoll, A.,
Heats of formation of alkyl radicals from appearance energies,
J. Am. Chem. Soc., 1988, 110, 7339. [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
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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]
Tarjan, Nyiredy, et al., 1989
Tarjan, G.; Nyiredy, Sz.; Gyor, M.; Lombosi, E.R.; Lombosi, T.S.; Budahegyi, M.V.; Meszaros, S.Y.; Takacs, J.M.,
Review. Thirtieth Anniversary of the Retention Index According to Kovats in Gas-Liquid Chromatography,
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. [all data]
Haken and Korhonen, 1985
Haken, J.K.; Korhonen, I.O.O.,
Gas-liquid chromatography of homologous esters. XXIX. Propanoyl and monochlorpropanoyl esters of lower saturated branched-chain and unsaturated alcohols,
J. Chromatogr., 1985, 324, 343-353, https://doi.org/10.1016/S0021-9673(01)81333-9
. [all data]
Haken, Madden, et al., 1985
Haken, J.K.; Madden, B.G.; Korhonen, I.O.O.,
Gas chromatography of homologous esters. XXXI. Butanoyl and monochlorobutanoyl esters of lower saturated branched chain and unsaturated alcohols on SE-30 and OV-351 capillary columns,
J. Chromatogr., 1985, 325, 61-73, https://doi.org/10.1016/S0021-9673(00)96008-4
. [all data]
Tiess, 1984
Tiess, D.,
Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30,
Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [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]
Zarazir, Chovin, et al., 1970
Zarazir, D.; Chovin, P.; Guiochon, G.,
Identification of hydroxylic compounds and their derivatives by gas chromatography,
Chromatographia, 1970, 3, 4, 180-195, https://doi.org/10.1007/BF02269018
. [all data]
Korhonen, 1984
Korhonen, I.O.O.,
Gas-Liquid Chromatographic Analyses. XXV. Branched-Chain C3-C5 Alkyl Esters of Halogenated Acetic Acids,
J. Chromatogr., 1984, 288, 51-69, https://doi.org/10.1016/S0021-9673(01)93681-7
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Tret'yakov, 2007
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]
Liu, Yang, et al., 2001
Liu, T.-T.; Yang, T.-S.; Wu, C.-M.,
Changes of volatiles in soy sauce-stewed pork during cold storage and reheating,
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Bianchi, Careri, et al., 2007
Bianchi, F.; Careri, M.; Mangia, A.; Musci, M.,
Retention indices in the analysis of food aroma volatile compounds in temperature-programmed gas chromatography: Database creation and evaluation of precision and robustness,
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Yasuhara, 1987
Yasuhara, A.,
Identification of Volatile Compounds in Poultry Manure by Gas Chromatography-Mass Spectrometry,
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. [all data]
Rapior, Breheret, et al., 1997
Rapior, S.; Breheret, S.; Talou, T.; Bessiére, J.-M.,
Volatile flavor constituents of fresh Marasmius alliaceus (garlic Marasmius),
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Larsen and Frisvad, 1995
Larsen, T.O.; Frisvad, J.C.,
Characterization of volatile metabolites from 47 Penicillium taxa,
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Anker, Jurs, et al., 1990
Anker, L.S.; Jurs, P.C.; Edwards, P.A.,
Quantitative structure-retention relationship studies of odor-active aliphatic compounds with oxygen-containing functional groups,
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del Rosario, de Lumen, et al., 1984
del Rosario, R.; de Lumen, B.O.; Habu, T.; Flath, R.A.; Mon, T.R.; Teranishi, R.,
Comparison of headspace volatiles from winged beans and soybeans,
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Feng and Mu, 2007
Feng, H.; Mu, L.-L.,
Quantitative structure-retention relationships for alkane and its derivatives based on electrotopological state index and molecular shape index,
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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]
Junkes, Castanho, et al., 2003
Junkes, B.S.; Castanho, R.D.M.; Amboni, C.; Yunes, R.A.; Heinzen, V.E.F.,
Semiempirical Topological Index: A Novel Molecular Descriptor for Quantitative Structure-Retention Relationship Studies,
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Estrada, E.; Gutierrez, Y.,
Modeling chromatographic parameters by a novel graph theoretical sub-structural approach,
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Zenkevich, 1998
Zenkevich, I.G.,
The Principle of Structural Analogy in the Calculation of Gas Chromatographic Retention Indices using Physico-Chemical Constants of Organic Compounds,
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Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
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Suhardi, Suzuki, et al., 2002
Suhardi, S.; Suzuki, M.; Yoshida, K.; Muto, T.; Fujita, A.; Watanbe, N.,
Changes in the volatile compounds and in the chemical and physical properties of snake fruit (Salacca edulis Reinw) Cv. Pondoh during maturation,
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Parada, Duque, et al., 2000
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Free and bound volatile composition and characterization of some glucoconjugates as aroma precursors in Melón de olor fruit pulp (Sicana odorifera),
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Pollak and Berger, 1996
Pollak, F.C.; Berger, R.G.,
Geosmin and Related Volatiles in Bioreactor-Cultured Streptomyces citreus CBS 109.60,
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Volatile compounds captured through purge and trap technique in caja-umbu (Spondias sp.) fruits during maturation,
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Notes
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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