Bsmoc-Cl

CAS 135204-19-2, Cat. No EN300-7441142
Reagent for amino group protection

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1,1-Dioxobenzo[b]-thiophene-2-yl methyloxycarbonyl chloride (Bsmoc-Cl) is a moisture-sensitive reagent used for amino group protection, particularly the α-amino function of amino acids¹. Bsmoc-Cl serves as an alternative to Fmoc in solid-phase and rapid continuous solution peptide synthesis². Bsmoc-protected amino acids offer advantages such as milder deprotection conditions (lower piperidine concentrations), minimizing base-induced side reactions. The reagent enables selective deprotection due to its distinct Michael-like addition mechanism, allowing orthogonal removal alongside Fmoc groups³. Bsmoc-Cl is stable when dry, soluble in common organic solvents. Hydrolysis occurs readily on silica gel, so it should be handled under anhydrous conditions.

Synonyms: Bsmoc-Cl; 1,1-dioxobenzo[b]thiophen-2-ylmethyl chloroformate; (1,1-dioxidobenzo[b]thiophen-2-yl)methyl carbonochloridate; (1,1-dioxo-1-benzothiophen-2-yl)methyl carbonochloridate; (1,1-dioxo-1lambda6-benzothiophen-2-yl)methyl chloroformate; benzo[b]thiophenesulfone-2-methyloxycarbonyl chloride; benzo[b]thiophenesulfone-2-methyl chloroformate