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In this chapter, we present a review on pyrazole fragmentation by gas chromatography coupled with mass spectrometry, in order to evaluate the substituent effect on pyrazole fragmentation. Our objective was to present a comprehensive study on the fragmentation pattern of substituted pyrazoles, contribute to the systematization of knowledge, and offer support to researchers in the characterization of pyrazoles via a comprehensive and versatile technique such as gas chromatography coupled with mass spectrometry. The pyrazole fragmentation showed two important processes: (i) expulsion of HCN from [M] +• and [M-H] + and (ii) the loss of N 2 from [M-H] +. Substituents such as D, Me, Br, Cl, and Ph did not influence these two processes; however, the presence of nitro, acetyl, oxime, diphenyl, or methyl and nitro in the ortho-position transforms the two processes into secondary fragmentation or results in their absence in the fragmentation of the said pyrazoles.

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