Derivatization Methods/Functional Groups Chart

Functional Group	Silylation	Acylation	Alkylation
Active Hydrogens	BSA, BSTFA, BSTFA/TCMS, Deriva-Sil, Hydrox-Sil, MSTFA, MTBSTFA, TMSI	PFPOH/PFPA	DMF Dialkylacetals, TBH
Carboxylic Acids	BSTFA, Hydrox-Sil Conc., MSTFA, TMSI	PFPOH/PFPA	BF3/Methanol, BF3/n-Butanol, DMF Dialkylacetals
Alcohols and Phenols: unhindered and moderately hindered	BSA, BSTFA/TCMS, HMDS, MTBSTFA/t-BDMCS	HFBI, Fluorinated Anhydrides (HFBA, PFPA, TFAA), MBTFA, MCF*	DMF Dialkylacetals, PFB-Br/TBA-H-SO4, TBH
Alcohols and Phenols: highly hindered	BSTFA/TCMS, Deriva-Sil, Deriva-Sil Conc.	Fluorinated Anhydrides, (HFBA, PFPA, TFAA), HFBI, PFBCI	DMF Dialkylacetals, PFB-Br/TBA-H-SO4, TBH
Amines: primary and secondary	BSTFA, MTBSTFA/t-BDMCS	Fluorinated Anhydrides, (HFBA, PFPA, TFAA), HFBI, MBTFA, PFBCI, TPC*	DMF Dialkylacetals, TBH
Amides	BSA, BSTFA, BSTFA/TMCS, Deriva-Sil Conc.	HFBI	DMF Dialkylacetals, TBH
Amino Acids	BSTFA, TMSI	HFBI (+ Silyation)	DMF Dialkylacetals, TBH
Catechloamines	TMSI	Fluorinated Anhydrides, (HFBA, PFPA, TFAA), HFBI
Carbohydrates and Sugars	HMDS, Hydrox-Sil AQ, TMSI	MBTFA
Inorganic Anions	BSTFA, MTBSTFA
Nitrosamines		HFBA
Sulfonamides	BSTFA	Fluorinated Anhydrides, (HFBA, PFPA, TFAA)	DMF Dialkylacetals, PFB-Br/TBA-H-SO4,
Derivatization reagents are listed in alphabetical order, not in order of preference.