Benzene, 1-(chloromethyl)-4-methyl-

• Formula: C₈H₉Cl
• Molecular weight: 140.610
• IUPAC Standard InChI: InChI=1S/C8H9Cl/c1-7-2-4-8(6-9)5-3-7/h2-5H,6H2,1H3 Copy

  
• IUPAC Standard InChIKey: DMHZDOTYAVHSEH-UHFFFAOYSA-N Copy
• CAS Registry Number: 104-82-5
• 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.
• Isotopologues:
  • [2H9]-1-(Chloromethyl)-4-methylbenzene
• Other names: p-Xylene, α-chloro-; α-Chloro-p-xylene; p-Chloromethyltoluene; p-Methylbenzyl chloride; p-Xylyl chloride; p-Xylyl-α-chloride; 1-(Chloromethyl)-4-methylbenzene; 4-Methylbenzyl chloride; 1-Methyl-4-(chloromethyl)benzene; 4-(Chloromethyl)toluene; p-Xylene, alpha-chloro-; (4-Methylphenyl)methyl chloride; NSC 46590; p-Tolylmethyl chloride
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Options:
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Reaction 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: John E. Bartmess

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

C₈H₈Cl^- +  =

By formula: C₈H₈Cl^- + H⁺ = C₈H₉Cl

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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₈H₈Cl^- +  =

By formula: C₈H₈Cl^- + H⁺ = C₈H₉Cl

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

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Hammad and Wenthold, 2000
Hammad, L.A.; Wenthold, P.G., Synthesis, characterization, and reactivity of the m-xylylene anion in the gas phase. The enthalpy of formation of m-xylylene, J. Am. Chem. Soc., 2000, 122, 45, 11203-11211, https://doi.org/10.1021/ja002138n . [all data]

Ponomarev, Takhimova, et al., 1974
Ponomarev, D.A.; Takhimova, V.V.; Akopyan, M.E.; Sergeyev, Y.L., Effect of alkyl groups on the stability of cations in the absence of solvation effects, Zh. Org. Khim., 1974, 10, 403. [all data]

Bermejo, Blanco, et al., 1986
Bermejo, J.; Blanco, C.G.; Guillén, M.D., Gas chromatography of deuterated and protiated chloro derivatives of 1,4-dimethylbenzene, J. Chromatogr., 1986, 351, 425-432, https://doi.org/10.1016/S0021-9673(01)83520-2 . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Zenkevich and Makarov, 2007
Zenkevich, I.G.; Makarov, A.A., Identification of Alkylarene Chloromethylation Products Using Gas-Chromatographic Retention Indices, Russian Journal of General Chemistry, 2007, 77, 4, 611-619, https://doi.org/10.1134/S1070363207040196 . [all data]

Zenkevich, 2001
Zenkevich, I.G., Interpretation of Gas Chromatographic Retention Indices in estimation of Structures of Isomeric Products of Radical Chlorinating of Alkyl Arenes, Zh. Org. Khim., 2001, 37, 2, 283-293. [all data]

Zenkevich, 1999
Zenkevich, I.G., Mutual Correlation between Gas-Chromatographic Retention Indices of Organic Compounds from Different Series, Zh. Anal. Khim., 1999, 54, 12, 1272-1279. [all data]

Notes

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• Symbols used in this document:
  

  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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