Oxirane, (chloromethyl)-

• Formula: C₃H₅ClO
• Molecular weight: 92.524
• IUPAC Standard InChI: InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2 Copy

  
• IUPAC Standard InChIKey: BRLQWZUYTZBJKN-UHFFFAOYSA-N Copy
• 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:
  • Oxirane, (chloromethyl)-
• Stereoisomers:
  • Oxirane, (chloromethyl)-, (R)-
  • (S)-(+)-Epichlorohydrin
• 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
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Appearance energy determinations

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.

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]

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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  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

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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