Propane, 2-chloro-2-methyl-
- Formula: C4H9Cl
- Molecular weight: 92.567
- IUPAC Standard InChIKey: NBRKLOOSMBRFMH-UHFFFAOYSA-N
- CAS Registry Number: 507-20-0
- 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: tert-Butyl Chloride; Trimethylchloromethane; 2-Chloro-2-methylpropane; 2-Chloroisobutane; 2-Methyl-2-chloropropane; 2-Methyl-2-propyl chloride; tert-C4H9Cl; Chlorotrimethylmethane; Tertiary-butyl chloride; NSC 6527
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Phase change data
Go To: Top, Gas phase ion energetics data, 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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 324.1 ± 0.9 | K | AVG | N/A | Average of 14 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 247. ± 3. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 247.53 | K | N/A | Dworkin and Guillamin, 1966 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 6.977 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 6.84 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 313. to 353. K.; AC |
ΔvapH° | 6.93 ± 0.02 | kcal/mol | C | Wadsö, Luoma, et al., 1968 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.585 | 324. | N/A | Majer and Svoboda, 1985 | |
7.72 | 268. | A | Stephenson and Malanowski, 1987 | Based on data from 253. to 358. K. See also Dykyj, 1971.; AC |
6.64 | 309. | A | Stephenson and Malanowski, 1987 | Based on data from 295. to 323. K. See also Calero, Valle, et al., 1969.; AC |
6.5 | 310. | N/A | Calero, Valle, et al., 1969 | Based on data from 295. to 323. K. See also Boublik, Fried, et al., 1984.; AC |
6.96 | 269. | N/A | Stull, 1947 | Based on data from 254. to 324. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
295. to 319.71 | 1.0485 | 110.567 | -221.514 | Calero, Valle, et al., 1969, 2 | Coefficents calculated by NIST from author's data. |
254. to 324. | 4.23630 | 1281.242 | -21.795 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
0.452 | 247.8 | DSC | Tamarit, López, et al., 2000 | AC |
0.471 | 248.1 | N/A | Lange, 1985 | AC |
0.476 | 248.4 | N/A | Urban, Janik, et al., 1972 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.450 | 182.9 | Dean, 1985 | CAL |
6.410 | 219.3 | ||
1.90 | 248.1 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.4479 | 182.91 | crystaline, III | crystaline, II | Dworkin and Guillamin, 1966, 2 | DH |
1.406 | 219.25 | crystaline, II | crystaline, I | Dworkin and Guillamin, 1966, 2 | DH |
0.4950 | 247.53 | crystaline, I | liquid | Dworkin and Guillamin, 1966, 2 | DH |
0.4099 | 183.1 | crystaline, III | crystaline, II | Kushner, Crowe, et al., 1950 | DH |
1.390 | 219.6 | crystaline, II | crystaline, I | Kushner, Crowe, et al., 1950 | DH |
0.4804 | 248.1 | crystaline, I | liquid | Kushner, Crowe, et al., 1950 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.450 | 182.91 | crystaline, III | crystaline, II | Dworkin and Guillamin, 1966, 2 | DH |
6.413 | 219.25 | crystaline, II | crystaline, I | Dworkin and Guillamin, 1966, 2 | DH |
2.00 | 247.53 | crystaline, I | liquid | Dworkin and Guillamin, 1966, 2 | DH |
2.2 | 183.1 | crystaline, III | crystaline, II | Kushner, Crowe, et al., 1950 | DH |
6.33 | 219.6 | crystaline, II | crystaline, I | Kushner, Crowe, et al., 1950 | DH |
1.9 | 248.1 | crystaline, I | liquid | Kushner, Crowe, et al., 1950 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, 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:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.58 | EST | Luo and Pacey, 1992 | LL |
10.3 ± 0.1 | EI | Baldwin, Maccoll, et al., 1964 | RDSH |
10.61 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
10.69 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.76 | PE | Flamini, Semprini, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H8+ | 9.56 | HCl | EI | Baldwin, Maccoll, et al., 1966 | RDSH |
C4H9+ | 10.51 ± 0.01 | Cl | PI | McLoughlin and Traeger, 1979 | LLK |
C4H9+ | 10.80 ± 0.07 | Cl | EI | Baldwin, Maccoll, et al., 1966 | RDSH |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Dworkin and Guillamin, 1966
Dworkin, A.; Guillamin, M.,
Specific heat of tert-butyl chloride at low temperature,
J. Chim. Phys. Phys.-Chim. Biol., 1966, 63, 53. [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]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [all data]
Wadsö, Luoma, et al., 1968
Wadsö, Ingemar; Luoma, Sinikka; Olson, Thomas; Norin, Torbjörn,
Heats of Vaporization of Organic Compounds. II. Chlorides, Bromides, and Iodides.,
Acta Chem. Scand., 1968, 22, 2438-2444, https://doi.org/10.3891/acta.chem.scand.22-2438
. [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]
Dykyj, 1971
Dykyj, J.,
Petrochemia, 1971, 11, 2, 27. [all data]
Calero, Valle, et al., 1969
Calero, G.C.; Valle, M.M.; Losa, C.G.,
Rev. Acad. Cienc. Fis. Quim. Nat. Zaragoza, 1969, 24, 2, 137. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Calero, Valle, et al., 1969, 2
Calero, G.C.; Valle, M.M.; Losa, C.G.,
Estudio Termodinamico del Sistema 2-Cloro, 2-Metilpropano 2-Bromo, 2-Metilpropano,
Rev. Acad. Cienc. Exactas Fis. Quim. Nat. Zaragoza, 1969, 24, 2, 137-158. [all data]
Tamarit, López, et al., 2000
Tamarit, J.Ll.; López, D.O.; Alcobé, X.; Barrio, M.; Salud, J.; Pardo, L.C.,
Thermal and Structural Characterization of (CH 3 ) 3 CCl,
Chem. Mater., 2000, 12, 2, 555-563, https://doi.org/10.1021/cm9911565
. [all data]
Lange, 1985
Lange, N.A.,
Lange's Handbook of Chemistry, 13th Edition, J.A. Dean, ed(s)., McGraw-Hill, New York, NY, 1985, 1792. [all data]
Urban, Janik, et al., 1972
Urban, S.; Janik, J.A.; Lenik, J.; Mayer, J.; Waluga, T.; Wróbel, S.,
Calorimetric, dielectric, and infrared investigations of solid t-butyl chloride,
Phys. Stat. Sol. (a), 1972, 10, 1, 271-280, https://doi.org/10.1002/pssa.2210100132
. [all data]
Dean, 1985
Dean, J.A.,
Lange's Handbook of Chemistry, 1985, McGraw-Hill. [all data]
Dworkin and Guillamin, 1966, 2
Dworkin, A.; Guillamin, M.,
Chaleur specifique du chlorure de tertiobutyle a basse temperature,
J. chim. Phys. physicochim., 1966, 63, 53-58. [all data]
Kushner, Crowe, et al., 1950
Kushner, L.M.; Crowe, R.W.; Smyth, C.P.,
The heat capacities and dielectric constants of some alkyl halides in the solid state,
J. Am. Chem. Soc., 1950, 72, 1091-1098. [all data]
Luo and Pacey, 1992
Luo, Y.-R.; Pacey, P.D.,
Effects of alkyl substitution on ionization energies of alkanes and haloalkanes and on heats of formation of their molecular cations. Part 2. Alkanes and chloro-, bromo- and iodoalkanes,
Int. J. Mass Spectrom. Ion Processes, 1992, 112, 63. [all data]
Baldwin, Maccoll, et al., 1964
Baldwin, M.; Maccoll, A.; Miller, S.I.,
Appearance potentials of the lower chloroalkanes,
J. Am. Chem. Soc., 1964, 86, 4498. [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]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Flamini, Semprini, et al., 1976
Flamini, A.; Semprini, E.; Stefani, F.; Sorriso, S.; Cardaci, G.,
He(I) photoelectron spectra and semiempirical molecular-orbital calculations on methylmetal halides of group 4A elements,
J. Chem. Soc. Dalton Trans., 1976, 731. [all data]
Baldwin, Maccoll, et al., 1966
Baldwin, M.; Maccoll, A.; Miller, S.I.,
Ionization and appearance potentials from a study of alkyl chlorides,
Advan. Mass Spectrom., 1966, 3, 259. [all data]
McLoughlin and Traeger, 1979
McLoughlin, R.G.; Traeger, J.C.,
Heat of formation for tert-butyl cation in the gas phase,
J. Am. Chem. Soc., 1979, 101, 5791. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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