Cyclohexanone, 3-methyl-
- Formula: C7H12O
- Molecular weight: 112.1696
- IUPAC Standard InChI: InChI=1S/C7H12O/c1-6-3-2-4-7(8)5-6/h6H,2-5H2,1H3
- IUPAC Standard InChIKey: UJBOOUHRTQVGRU-UHFFFAOYSA-N
- CAS Registry Number: 591-24-2
- 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: 3-Methylcyclohexanone; Methyl-3 cyclohexanone-1
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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:
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 |
|---|---|---|---|---|---|
| ΔcH°liquid | -1002.9 | kcal/mol | Ccb | Zubova, 1901 | Corresponding ΔfHºliquid = -65.3 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 |
|---|---|---|---|
| 49.50 | 290. | Herz and Bloch, 1924 | DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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:
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 442.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Tboil | 442.7 | K | N/A | White and Bishop, 1940 | Uncertainty assigned by TRC = 0.7 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 199.25 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Tfus | 184. | K | N/A | White and Bishop, 1940 | Uncertainty assigned by TRC = 6. K; TRC |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 10.7 | 349. | Aucejo, Monton, et al., 1993 | Based on data from 334. - 441. K.; AC |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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 by: 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
=
+
By formula: C7H14O = H2 + C7H12O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14.9 ± 0.50 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 488 K |
=
+
By formula: C7H14O = H2 + C7H12O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.7 ± 0.50 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 488 K |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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 by: John E. Bartmess
View reactions leading to C7H12O+ (ion structure unspecified)
Electron affinity determinations
| EA (eV) | Reference | Comment |
|---|---|---|
| 0.008718 ± 0.000087 | Hammer, Diri, et al., 2003 |
IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
| 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 | Sadtler Research Labs Under US-EPA Contract |
| State | gas |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
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-5017 |
| NIST MS number | 230134 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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. | 937. | Golovnya, Syomina, et al., 1997 | 25. m/0.32 mm/1. μm, He |
| Capillary | SE-30 | 110. | 939. | Golovnya, Syomina, et al., 1997 | 25. m/0.32 mm/1. μm, He |
| Capillary | SE-30 | 80. | 931. | Golovnya, Syomina, et al., 1997 | 25. m/0.32 mm/1. μm, He |
| Capillary | SE-30 | 90. | 934. | Golovnya, Syomina, et al., 1997 | 25. m/0.32 mm/1. μm, He |
| Packed | Apiezon L | 130. | 961. | Paris and Alexandre, 1972 | Chromosorb W AW |
| Packed | Apiezon L | 130. | 943. | Wehrli and Kováts, 1959 | Celite; Column length: 2.25 m |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 985. | Ohnishi and Shibamoto, 1984 | 2. K/min; Column length: 50. m; Column diameter: 0.23 mm; Tstart: 80. C; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 945. | Buchman, Cao, et al., 1984 | He, Chromosorb AW, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m |
| Packed | SE-30 | 945. | Buchman, Cao, et al., 1984 | He, Chromosorb AW, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | Carbowax 20M | 1376. | Buchman, Cao, et al., 1984 | He, Supelcoport, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m |
| Packed | Carbowax 20M | 1376. | Buchman, Cao, et al., 1984 | He, Supelcoport, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m |
Normal alkane RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | DB-1 | 60. | 915. | Shimadzu, 2003 | 60. m/0.32 mm/1. μm, He |
| Capillary | DB-1 | 80. | 924. | Shimadzu, 2003 | 60. m/0.32 mm/1. μm, He |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | BP-1 | 931. | Health Safety Executive, 2000 | 50. m/0.22 mm/0.75 μm, He, 5. K/min; Tstart: 50. C; Tend: 200. C |
| Packed | SE-30 | 945. | Peng, Ding, et al., 1988 | Helium, Supelcoport, 40. C @ 4. min, 10. K/min, 200. C @ 60. min; Column length: 3.05 m |
| Packed | SE-30 | 946. | Peng, Ding, et al., 1988 | Helium, Supelcoport, 40. C @ 4. min, 10. K/min, 200. C @ 60. min; Column length: 3.05 m |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SPB-1 | 922. | Díaz-Maroto, Castillo, et al., 2007 | 50. m/0.25 mm/0.25 μm; Program: 70C(3min) => 4C/min => 120C => 8C/min => 250C(5min) |
| Capillary | SPB-1 | 922. | Díaz-Maroto, Castillo, et al., 2007 | 50. m/0.25 mm/0.25 μm; Program: 70C(3min) => 4C/min => 120C => 8C/min => 250C(5min) |
| Capillary | Methyl Silicone | 928. | Zenkevich, 1998 | Program: not specified |
Normal alkane RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | DB-Wax | 60. | 1333. | Shimadzu, 2003 | 50. m/0.32 mm/1. μm, He |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | TC-Wax | 1333. | Shuichi, Masazumi, et al., 1996 | 80. C @ 5. min, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 240. C |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | BP-20 | 1381. | Rodrigues, Caldera, et al., 2008 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (1 min) 2 0C/min -> 100 0C (2 min) 1.7 0C/min -> 180 0C (1 min) 25 0C/min -> 220 0C (10 min) |
| Capillary | BP-20 | 1381. | Rodrigues, Caldera, et al., 2008 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (1 min) 2 0C/min -> 100 0C (2 min) 1.7 0C/min -> 180 0C (1 min) 25 0C/min -> 220 0C (10 min) |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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.
Zubova, 1901
Zubova, P.,
Data about heat of combustion of compound cycle structure,
Zh. Fiz. Khim., 1901, 33, 708-722. [all data]
Herz and Bloch, 1924
Herz, W.; Bloch, W.,
Physikalisch-chemische Untersuchungen an Verbindungen der Cyklohexanreihe,
Z. Phys. Chem., 1924, 110, 23-39. [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]
White and Bishop, 1940
White, A.H.; Bishop, W.S.,
Dielectric Evidence of Molecular Rotation in the Crystals of Certain Non-aromatic Compounds,
J. Am. Chem. Soc., 1940, 62, 8-16. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Aucejo, Monton, et al., 1993
Aucejo, Antonio; Monton, Juan B.; Munoz, Rosa; Sanchotello, Margarita,
Isobaric vapor-liquid equilibrium data for the cyclohexanone + N-methylacetamide system,
J. Chem. Eng. Data, 1993, 38, 1, 160-162, https://doi.org/10.1021/je00009a039
. [all data]
Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya.,
Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions,
Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]
Hammer, Diri, et al., 2003
Hammer, N.I.; Diri, K.; Jordan, K.D.; Desfrancois, C.; Compton, R.N.,
Dipole-bound anions of carbonyl, nitrile, and sulfoxide containing molecules,
J. Chem. Phys., 2003, 119, 7, 3650-3660, https://doi.org/10.1063/1.1590959
. [all data]
Golovnya, Syomina, et al., 1997
Golovnya, R.V.; Syomina, L.A.; Samusenko, A.L.,
Temperature changes of sorption parameters of di-n-alkylketones and methylcyclohexanones in capillary gas chromatography,
Russ. Chem. Bull. (Engl. Transl.), 1997, 46, 2, 314-318, https://doi.org/10.1007/BF02494370
. [all data]
Paris and Alexandre, 1972
Paris, C.; Alexandre, P.,
Stereochemical Investigation of Cyclohexane and Terpene Compounds by Gas Chromatography,
J. Chromatogr. Sci., 1972, 10, 6, 402-411, https://doi.org/10.1093/chromsci/10.6.402
. [all data]
Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E.,
Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen,
Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745
. [all data]
Ohnishi and Shibamoto, 1984
Ohnishi, S.; Shibamoto, T.,
Volatile compounds from heated beef fat and beef fat with glycine,
J. Agric. Food Chem., 1984, 32, 5, 987-992, https://doi.org/10.1021/jf00125a008
. [all data]
Buchman, Cao, et al., 1984
Buchman, O.; Cao, G.-Y.; Peng, C.T.,
Structure assignment by retention index in gas-liquid radiochromatography of substituted cyclohexenes,
J. Chromatogr., 1984, 312, 75-90, https://doi.org/10.1016/S0021-9673(01)92765-7
. [all data]
Shimadzu, 2003
Shimadzu,
Gas chromatography analysis of organic solvents using capillary columns (No. 3), 2003, retrieved from http://www.shimadzu.com/apps/form.cfm. [all data]
Health Safety Executive, 2000
Health Safety Executive,
MDHS 96 Volatile organic compounds in air - Laboratory method using pumed solid sorbent tubes, solvent desorption and gas chromatography
in Methods for the Determination of Hazardous Substances (MDHS) guidance, Crown, Colegate, Norwich, 2000, 1-24, retrieved from http://www.hse.gov.uk/pubns/mdhs/pdfs/mdhs96.pdf. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.,
Radioimpurity identification by retention index in tritium labeling,
J. Radioanal. Nucl. Chem., 1988, 123, 2, 411-420, https://doi.org/10.1007/BF02034907
. [all data]
Díaz-Maroto, Castillo, et al., 2007
Díaz-Maroto, M.C.; Castillo, N.; Castro-Vázquez, L.; González-Viñas, M.A.; Pérez-Coello, M.S.,
Volatile composition and olfactory profile of pennyroyal (Mentha pulegium L.) plants,
Flavour Fragr. J., 2007, 22, 2, 114-118, https://doi.org/10.1002/ffj.1766
. [all data]
Zenkevich, 1998
Zenkevich, I.G.,
Non-Traditional Criteria for Gas-Chromatographic and Chromato-Mass-Spectrometric Identification of Organic Compounds,
Zh. Anal. Khim., 1998, 53, 8, 828-835. [all data]
Shuichi, Masazumi, et al., 1996
Shuichi, H.; Masazumi, N.; Hiromu, K.; Kiyoshi, F.,
Comparison of volatile compounds berween the crude drugs, Onji-tsutsu and Onji-niki,
Nippon nogei kagaku kaishi, 1996, 70, 2, 151-160. [all data]
Rodrigues, Caldera, et al., 2008
Rodrigues, F.; Caldera, M.; Camara, J.S.,
development of a dynamic headspace solid-phase microextraction procedure coupled to GC-qMSD for evaluation the chemical profile in alcoholic beverages,
Anal. Chim. Acta, 2008, 609, 1, 82-104, https://doi.org/10.1016/j.aca.2007.12.041
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.