Citation: WANG Min. Reversed-phase high performance liquid chromatography separation of 2-(fluorophenyl)-5-methylbenzoxazole and 2-(chlorophenyl)-5-methylbenzoxazole positional isomers[J]. Chinese Journal of Chromatography, ;2013, 31(8): 758-762. doi: 10.3724/SP.J.1123.2013.01030 shu

Reversed-phase high performance liquid chromatography separation of 2-(fluorophenyl)-5-methylbenzoxazole and 2-(chlorophenyl)-5-methylbenzoxazole positional isomers

WANG Min ^,

1.
Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China

Corresponding author: WANG Min,
Received Date: 14 January 2013
Available Online: 10 March 2013

The analytical method of 2-(fluorophenyl)-5-methylbenzoxazole ortho-, meta-, para-positional isomers and 2-(chlorophenyl)-5-methylbenzoxazole ortho-, meta-, para-positional isomers was developed with a commercial common liquid chromatography column. The separation was performed on an Inertsil ODS-SP C₁₈ column (250 mm×4.6 mm, 5 μm) at 40℃ with a linear gradient elution by mobile phases of acetonitrile (A) (from 60% to 80% within 15 min) and water (B) at a flow rate of 1.5 mL/min. The samples were detected by a diode array detector at 310 nm. Good linearities were obtained in the range of 2-200 mg/L for the six isomers. The limits of detection (LODs) (S/N=3) of 2-(fluorophenyl)-5-methylbenzoxazole ortho-, meta-, para-isomers and 2-(chlorophenyl)-5-methylbenzoxazole ortho-, meta-, para-isomers were 0.0307, 0.0293, 0.0315, 0.0226, 0.0237, 0.0226 mg/L, respectively. The method provides not only a rapid detection method for the preparation of the isomers through hydrocarbon activation coupling reaction between the 5-methylbenzoxazole and fluorobenzene or chlorobenzene but also a reference for the separation and detection of 2-arylbenzoxazole isomers.
- high performance liquid chromatography (HPLC),
- benzoxazole,
- positional isomers,
- C₁₈ column
1. [1]
  [1] Vinsova J, Cermakova K, Tomeckova A, et al. Bioorg Med Chem, 2006, 14(17): 5850
2. [2]
  [2] Lokwani P, Nagori B P, Batra N, et al. J Chem Pharm Res, 2011, 3(3): 302
3. [3]
  [3] Prajapat R P, Soni B, Bhandari A, et al. Pharm Lett, 2011, 3(3): 161
4. [4]
  [4] Shrivastava B, Sharma V, Lokwani P. Pharmacologyonline, 2011, 1: 236
5. [5]
  [5] Kumar D, Jacob M R, Reynolds M B, et al. Bioorg Med Chem, 2002, 10(12): 3997
6. [6]
  [6] Xia T, Meng Q H, Geng Y C, et al. Dyestuffs and Coloration (夏天, 孟庆华, 耿彦朝, 等. 染料与染色), 2007, 44(6): 37
7. [7]
  [7] Xiao J P, Zhu B J, Shi Z Q, et al. Dyestuffs and Coloration (肖锦平, 竹百均, 石赵泉, 等. 染料与染色), 2008, 45(5): 20
8. [8]
  [8] Ge G Z. Textile Auxiliaries (葛广周. 印染助剂), 2010, 27(1): 4
9. [9]
  [9] Ge G Z, Zhou Y. Dyestuffs and Coloration (葛广周, 周赟. 染料与染色), 2011, 48(1): 39
10. [10]
  [10] Kumar R V. Asian J Chem, 2004, 16(3/4): 1241
11. [11]
  [11] Kumar A, Maurya R A, Saxena D. Mol Divers, 2010, 14(2): 331
12. [12]
  [12] Bala S, Saini M, Kamboj S. Int J ChemTech Res, 2011, 3(3): 1102
13. [13]
  [13] Wu G, Zhou J, Zhang M, et al. Chem Commun, 2012, 48(71): 8964
14. [14]
  [14] Pino V, Afonso A M, Gonzalez V, et al. J Liq Chromatogr Relat Technol, 2003, 26(1): 1
15. [15]
  [15] Mauri-Aucejo A R, Llobat-Estelles M, Escarti-Carrasco M, et al. Anal Lett, 2006, 39(1): 183
16. [16]
  [16] Schurenkamp J, Beike J, Pfeiffer H, et al. Int J Legal Med, 2011, 125(1): 95
17. [17]
  [17] Qiu H D, Mallik A K, Takafuji M, et al. Anal Chim Acta, 2012, 738: 95
18. [18]
  [18] Chen P R, Zhang M J. J Chromatogr A, 1997, 773(1/2): 365
19. [19]
  [19] Liang Y C, Yi Z Z, Cai Z H, et al. Chinese Journal of Chromatography (梁奕昌, 义志忠, 蔡志虹, 等. 色谱), 1999, 17(4): 397
20. [20]
  [20] Narvekar M S, Srivastava A K. J Liq Chromatogr Relat Technol, 2003, 26(1): 85
21. [21]
  [21] Nunes I L, Mercadante A Z. Rev Bras Cienc Farm, 2006, 42(4): 539
22. [22]
  [22] Suzuki Y, Miseki K, Shimma S, et al. Bunseki Kagaku, 2007, 56(3): 191
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