1-hydroxy-1H-Benzotriazole, CAS No. 2592-95-2

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2592-95-2

Catalog No. EBD11855

CAS 2592-95-2

Name 1-hydroxy-1H-Benzotriazole

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Basic Information

Synonyms: 1-Hydroxybenzotriazole HOBT N-Hydroxybenzotrizole 1-Hydroxybenzotrizole HOBt(anhydrous) 1-hydroxylbenzotriazole 1-hydroxybenzotriazol 1-hydroxybenzotriazoleanhydrous 1-hydroxy-1-h-benzotriazole 1-hydroxy-1,2,3-benzotriazole 1-hob 1h-benzotriazole,1-hydroxy- 1-hydroxy-1H-Benzotriazole

Molecular Formula: C6H5N3O

Molecular Weight: 135.12

MDL Number: MFCD00005805

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Condensation Reagents Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates

Product Description:

1-Hydroxybenzotriazole (HOBt, CAS 2592-95-2) is a white to off-white crystalline powder with the molecular formula C6H5N3O. It is a heterocyclic compound containing a benzotriazole ring system substituted with a hydroxyl group. HOBt is a fundamental and widely used reagent in peptide synthesis and other amide bond formation reactions. Its primary function is as an additive or active ester component in conjunction with coupling reagents like DCC (dicyclohexylcarbodiimide) or EDC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide). HOBt acts by forming an active ester intermediate with the carboxylic acid, which is more reactive towards nucleophilic attack by amines but significantly reduces the risk of racemization of chiral amino acids compared to direct coupling methods. This makes it indispensable in solid-phase peptide synthesis (SPPS) and solution-phase synthesis of peptides, peptidomimetics, and other amide-containing compounds. Due to its critical role in constructing the peptide backbone, a core structure in many pharmaceuticals, HOBt is also considered a key pharmaceutical intermediate. It is handled as a standard laboratory chemical but requires caution as it can be explosive when dry or in large quantities.

Physical Properties

Melting Point: 156-159°C

Boiling Point: 149-150 °C

Flash Point: 95 °C

Density: 1 g/cm3

Refractivity: n20/D 1.488

Storage: Store at RT.

Analytical Data

Appearance: white to light yellow powder