1-Hydroxybenzotriazole

Lygo, Barry; Pelletier, Guillaume

doi:10.1002/047084289x.rh052.pub2

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2019

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“…1-Hydroxybenzotriazole, or HOBt (1, see Figure 1), is a heterocycle most often used as a catalytic or stoichiometric additive to accelerate nucleophilic acyl substitution reactions, particularly amidations. 1 For amidation reactions mediated by a carbodiimide, addition of HOBt typically results in improved reaction rates, fewer side products, and diminished epimerization at α-chiral centers. 2 The importance of HOBt in chemical synthesis is evident by its role as a reactant, reagent, or catalyst in more than six million reactions reported in the chemical literature.…”

Section: ■ Introductionmentioning

confidence: 99%

Mutagenic Impurities in 1-Hydroxybenzotriazole (HOBt)

Treitler

Marriott

Chadwick

et al. 2019

Org. Process Res. Dev.

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1-Hydroxybenzotriazole (HOBt) is a nucleophilic additive widely utilized in synthetic chemistry. During process optimization for an amidation reaction employing HOBt, the presence of two hydrazide impurities was ultimately traced back to hydrazine contamination of HOBt. An analytical method for HOBt able to quantify trace levels of hydrazine and 1-chloro-2-nitrobenzene (another putative mutagenic impurity) was developed and validated. Nearly two dozen batches of commercial HOBt from several vendors were tested and revealed occasional, variable contamination with low levels of hydrazine.

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Section: ■ Introductionmentioning

confidence: 99%