1-Hydroxybenzotriazole

Chemical properties

white to light yellow powder

Physical properties

1-Hydroxybenzotriazole is a white crystalline powder, which as a commercial product contains some water.

The Uses of 1-Hydroxybenzotriazole

1-Hydroxybenzotriazole (HOBT) is used in preparation method of carbon fiber/polyamide composite powder material for laser sintering.

Preparation

To a  solution of the SM (1.0 g, 6.4 mmol)  in DMF (5.0 mL) at 0℃ was added EDC-HCl (1.2 g, 7.7 mmol), NH4Cl (1.4 g, 26.9 mmol),  and HOBt (1.1 g, 8.3 mmol). The reaction  mixture was stirred at RT for 12 h, after which time ice-cold H2O was added and the mixture was extracted with EtOAc. The org layer was dried (Na2SO4)  and concentrated in vacuo to provide the product as an orange/red solid. [600 mg,  61%]

The Uses of 1-Hydroxybenzotriazole

additive for oligonucleotide couplings and in racemization-free peptide couplings

Definition

ChEBI: 1-Hydroxybenzotriazole is a member of benzotriazoles.

Flammability and Explosibility

Not classified

Biological Activity

hydroxy benzotriazole, abbreviated hobt, is anorganic compoundthat is a derivative of benzotriazole. hobt, as a commercial product, is a white crystalline powder contains some water (~11.7% wt as the hobt monohydrate crystal). it is mainly used to suppress the racemization of single-enantiomerchiral molecules and to improve the efficiency ofpeptide synthesis. automated peptide synthesisinvolves the condensation of the amino group of protected amino acidswith the activated ester. hobt can be used to produce activated esters such as n-hydroxysuccinimide ester. these esters are insoluble and react with amines at ambient temperature to give amides [1]. hobt is also used for the synthesis of amides from carboxylic acidsaside from amino acids. these substrates may not be convertible to theacyl chlorides [2]. for instance amide derivatives of ionophoric antibiotics have been prepared in this way [3].

Purification Methods

Crystallise HOBt from aqueous EtOH or water. [Boyle & Jones J Chem Soc Perkin Trans II 160 1973, Tomita & Ikawa J Pharm Soc Jpn 75 449 1955, Beilstein 26 III/IV 95.]

References

[1]. knig w, geiger r. eineneuemethodezursynthese von peptiden: aktivierung der carboxylgruppemitdicyclohexylcarbodiimidunterzusatz von 1‐hydroxy‐benzotriazolen[j]. chemischeberichte, 1970, 103(3): 788-798.
[2]. myers a g, yang b h, chen h. transformation of pseudoephedrine amides into highly enantiomerically enriched aldehydes, alcohols, and ketones[j]. organic syntheses, 2000: 29-29.
[3]. owicki d, huczyński a, ratajczak-sitarz m, et al. structural and antimicrobial studies of a new n-phenylamide of monensin a complex with sodium chloride[j]. journal of molecular structure, 2009, 923(1): 53-59.