1-Hydroxybenzotriazole Chemical Properties

Melting point:

156-159°C

Boiling point:

149-150 °C

Density 

1 g/cm³

vapor pressure 

0.009Pa at 25℃

refractive index 

n20/D 1.488

Flash point:

95 °C

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

7.39±0.58(Predicted)

color 

White to off-white crystalline powder

Water Solubility 

4.201g/L at 29℃

Stability:

Stable, but possible risk of explosion if heated under confinement. Flammable.

LogP

0.146 at 25℃

CAS DataBase Reference

2592-95-2(CAS DataBase Reference)

NIST Chemistry Reference

1H-benzotriazole, 1-hydroxy-(2592-95-2)

EPA Substance Registry System

1H-Benzotriazole, 1-hydroxy- (2592-95-2)

Safety Information

Hazard Codes 

F,Xi,T,E

Risk Statements 

11-5-36/38-36/37/38-36-20/21-61-2

Safety Statements 

16-33-7/9-26-45-53-15-36/37-35

RIDADR 

1325

RTECS 

DM1288000

HazardClass 

4.1

PackingGroup 

III

HS Code 

29339980

Toxicity

rat,LDLo,oral,5gm/kg (5000mg/kg),Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 679, 1992.

MSDS

• Language:English Provider:1-Hydroxybenzotriazole
• Language:English Provider:ALFA

1-Hydroxybenzotriazole Usage And Synthesis

Chemical Properties

white to light yellow powder

Uses

additive for oligonucleotide couplings and in racemization-free peptide couplings

Uses

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

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].

target

racemization

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.

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