Oxirane, (chloromethyl)-
- Formula: C3H5ClO
- Molecular weight: 92.524
- IUPAC Standard InChIKey: BRLQWZUYTZBJKN-UHFFFAOYSA-N
- CAS Registry Number: 106-89-8
- 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. - Species with the same structure:
- Stereoisomers:
- Other names: Propane, 1-chloro-2,3-epoxy-; α-Epichlorohydrin; γ-Chloropropylene oxide; (Chloromethyl)ethylene oxide; (Chloromethyl)oxirane; Chloropropylene oxide; Epichlorohydrin; Glycerol epichlorohydrin; Glycidyl chloride; SKEkhG; 1-Chloro-2,3-Epoxypropane; 1,2-Epoxy-3-chloropropane; 2-(Chloromethyl)oxirane; 2,3-Epoxypropyl chloride; 3-Chloro-1,2-epoxypropane; 3-Chloro-1,2-propylene oxide; 3-Chloropropene-1,2-oxide; 3-Chloropropylene oxide; (DL)-α-Epichlorohydrin; Epichlorhydrin; Epichloorhydrine; Epichlorhydrine; Epichlorohydryna; Epicloridrina; Glycerol epichlorhydrin; Oxirane, 2-(chloromethyl); 1-Chloor-2,3-epoxy-propaan; 1-Chlor-2,3-epoxy-propan; 1-Cloro-2,3-epossipropano; Epichlorophydrin; Rcra waste number U041; UN 2023; NSC 6747
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -108. ± 4.2 | kJ/mol | Ccr | Bjellerup and Smith, 1954 | Heat of formation derived by Cox and Pilcher, 1970 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -149. ± 0.4 | kJ/mol | Ccr | Bjellerup and Smith, 1954 | At 293 K |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1770. ± 0.4 | kJ/mol | Ccr | Bjellerup and Smith, 1954 | At 293 K |
ΔcH°liquid | -1761.64 ± 0.77 | kJ/mol | Ccb | Nilsson and Smith, 1944 | |
ΔcH°liquid | -1235.80 ± 0.85 | kJ/mol | Ccb | Smith and Schjdnberg, 1931 | Not corrected for CODATA value of ΔfH |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 389.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 390. | K | N/A | Rofman, Yakubov, et al., 1976 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 389.6 | K | N/A | Lecat, 1947 | Uncertainty assigned by TRC = 0.7 K; TRC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
41. ± 4.2 | 293. | E | Bjellerup and Smith, 1954 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
42.9 | 272. | N/A | Stull, 1947 | Based on data from 256. to 391. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
256.7 to 391.1 | 4.66829 | 1642.508 | -38.8 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics 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:
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 |
---|---|---|---|
10.66 | EI | Vorob'ev, Furlei, et al., 1989 | Vertical value; LL |
10.60 | PE | McAlduff and Houk, 1977 | Vertical value; LLK |
10.64 | PE | Baker, Betteridge, et al., 1971 | Vertical value; LLK |
10.64 | PE | Baker, Betteridge, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 12.0 ± 0.5 | ? | EI | Wada and Kiser, 1962 | RDSH |
CH2+ | 21.6 ± 0.5 | ? | EI | Wada and Kiser, 1962 | RDSH |
CH2Cl+ | 12.5 ± 0.1 | ? | EI | Wada and Kiser, 1962 | RDSH |
CH3+ | 14.6 | ? | EI | Wada and Kiser, 1962 | RDSH |
CH3O+ | 13.4 ± 0.2 | ? | EI | Wada and Kiser, 1962 | RDSH |
C2H2+ | 16.6 ± 0.1 | ? | EI | Wada and Kiser, 1962 | RDSH |
C2H2O+ | 12.1 ± 0.1 | ? | EI | Wada and Kiser, 1962 | RDSH |
C2H3+ | 14.0 ± 0.4 | ? | EI | Wada and Kiser, 1962 | RDSH |
C2H4+ | 13.6 ± 0.4 | ? | EI | Wada and Kiser, 1962 | RDSH |
C3H5O+ | 11.4 ± 0.3 | Cl | EI | Wada and Kiser, 1962 | RDSH |
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: Coblentz Society, Inc.
Condensed Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | COBLENTZ SOCIETY Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | WYANDOTTE CHEMICALS CORP., WYANDOTTE, MICHIGAN, USA |
Source reference | COBLENTZ NO. 946 |
Date | 1960 |
Name(s) | 2-(chloromethyl)oxirane |
State | LIQUID (SHELL CHEM. CO. COMM.) |
Instrument | Not specified, most likely a prism, grating, or hybrid spectrometer. |
Path length | 0.003 CM |
Resolution | 4 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY NIST FROM HARD COPY |
Gas Chromatography
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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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | SE-30 | 100. | 700. | Winskowski, 1983 | Gaschrom Q; Column length: 2. m |
Packed | Silicon High Vacuum Grease (obsolete) | 170. | 720. | Janák, Jonas, et al., 1965 | H2, Celite |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 708. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Capillary | SE-54 | 730. | Huang, Liang, et al., 1996 | 36. m/0.25 mm/0.25 μm, 5. K/min; Tstart: 35. C; Tend: 240. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-1 | 695. | Flanagan, Streete, et al., 1997 | 60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C |
Capillary | Polydimethyl siloxanes | 708. | Zenkevich and Chupalov, 1996 | Program: not specified |
Capillary | SPB-1 | 695. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C |
Capillary | SPB-1 | 720. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 700. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | OV-1 | 730. | Ramsey and Flanagan, 1982 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Superox 0.6; Carbowax 20M | 1169. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 1169. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Carbowax 20M | 1205. | Ramsey and Flanagan, 1982 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bjellerup and Smith, 1954
Bjellerup, L.; Smith, L.,
Heats of combustion of some organic chloro-compounds,
Kgl. Fysiograph. Sallskap. Lund Forh., 1954, 24, 1-13. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Nilsson and Smith, 1944
Nilsson, A.T.; Smith, L.,
Om de isomera epiklorhydrinerna,
Svensk. Kim. Tidr., 1944, 56, 156-175. [all data]
Smith and Schjdnberg, 1931
Smith, L.; Schjdnberg, E.,
Uber die Verbrennung von chlorhaltigen Substanzen in Berthelots Bombe,
Svensk Kemisk Tidskrift, 1931, 213-226. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Rofman, Yakubov, et al., 1976
Rofman, V.M.; Yakubov, R.D.; Trofimov, B.A.; Maksimov, S.M.,
Liq-vap. equil. in system formed by products of vinylation of triethylene glycol & product of epoxidation of ethylene glycol monovinyl ether witrh epichlorohydrin,
Zh. Prikl. Khim. (Leningrad), 1976, 49, 1159-61. [all data]
Lecat, 1947
Lecat, M.,
Orthobaric Azeotropes of Sulfides,
Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [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]
Vorob'ev, Furlei, et al., 1989
Vorob'ev, A.S.; Furlei, I.I.; Sultanov, A.S.; Khvostenko, V.I.; Leplyanin, G.V.; Derzhinskii, A.R.; Tolstikov, G.A.,
Mass spectrometry of reasonance capture of electrons and photoelectron spectroscopy of molecules of ethylene oxide, ethylene sulfide, and their derivatives,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 1388. [all data]
McAlduff and Houk, 1977
McAlduff, E.J.; Houk, K.N.,
Photoelectron spectra of substituted oxiranes and thiiranes. Substituent effects on ionization potentials involving σ orbitals,
Can. J. Chem., 1977, 55, 318. [all data]
Baker, Betteridge, et al., 1971
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E.,
Application of photoelectron spectrometry to pesticide analysis. II.Photoelectron spectra of hydroxy-, and halo-alkanes and halohydrins,
Anal. Chem., 1971, 43, 375. [all data]
Wada and Kiser, 1962
Wada, Y.; Kiser, R.W.,
Electron impact spectroscopy of some substituted oxiranes,
J. Phys. Chem., 1962, 66, 1652. [all data]
Winskowski, 1983
Winskowski, J.,
Gaschromatographische Identifizierung von Stoffen anhand von Indexziffem und unterschiedlichen Detektoren,
Chromatographia, 1983, 17, 3, 160-165, https://doi.org/10.1007/BF02271041
. [all data]
Janák, Jonas, et al., 1965
Janák, J.; Jonas, J.; Kratochvíl, M.,
Identification of some acetals of the tetrahydrofurane sereis by gas chromatography with the aid of the Kováts indices,
Collect. Czech. Chem. Commun., 1965, 30, 1, 265-276, https://doi.org/10.1135/cccc19650265
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Huang, Liang, et al., 1996
Huang, C.; Liang, H.; Han, S.,
The analysis of organic compounds in waste water by gas extraction/thermal desorption/gas chromatography-mass spectrometry,
Chin. J. Chromatogr., 1996, 14, 6, 421-424. [all data]
Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D.,
Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]
Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A.,
New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments,
Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]
Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J.,
Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning,
Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111
. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J.,
Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse,
J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point 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 ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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