2592-95-2 Usage
Description
1-Hydroxybenzotriazole, also known as HOBt, is an organic compound that is commonly used as a coupling agent in various chemical reactions. It is a white to light yellow powder and is known for its ability to enhance the efficiency of reactions by acting as a catalyst. Its chemical structure allows it to form stable adducts with carboxylic acids, which can improve the reactivity and selectivity of the reaction.
Uses
Used in Pharmaceutical Industry:
1-Hydroxybenzotriazole is used as a coupling agent in the synthesis of various pharmaceutical compounds. It helps to improve the efficiency of peptide coupling reactions, which are essential for the production of many drugs and therapeutic agents.
Used in Chemical Synthesis:
1-Hydroxybenzotriazole is used as a catalyst in various chemical reactions, including the formation of amides, esters, and other functional groups. Its ability to form stable adducts with carboxylic acids makes it a useful tool for improving the reactivity and selectivity of these reactions.
Used in Carbon Fiber/Polyamide Composite Powder Material Preparation:
1-Hydroxybenzotriazole is used in the preparation method of carbon fiber/polyamide composite powder material for laser sintering. It helps to improve the adhesion and compatibility between the carbon fiber and polyamide matrix, resulting in enhanced mechanical properties and performance of the composite material.
Overall, 1-Hydroxybenzotriazole is a versatile compound with a wide range of applications in various industries, including pharmaceuticals, chemical synthesis, and material science. Its unique chemical properties make it an essential tool for improving the efficiency and selectivity of many reactions and processes.
Flammability and Explosibility
Notclassified
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.
Check Digit Verification of cas no
The CAS Registry Mumber 2592-95-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,9 and 2 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2592-95:
(6*2)+(5*5)+(4*9)+(3*2)+(2*9)+(1*5)=102
102 % 10 = 2
So 2592-95-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H5N3O.H3N/c10-9-6-4-2-1-3-5(6)7-8-9;/h1-4,10H;1H3
2592-95-2Relevant articles and documents
Synthesis and morpholinolysis of N,N-diethyl carbamate derivatives of 4- HOAt, 7-HOAt and HOBt
Khattab, Sherine N.,Hassan, Seham Y.,Hamed, Ezzat A.,El-Faham, Ayman
, p. 247 - 251 (2007)
N,N-Diethyl carbamates of 1-hydroxy-7-azabenzotriazole (7-HOAt), 1-hydroxy-4-azabenzotriazole (4-HOAt), 1-hydroxybenzotriazole (HOBt), and 1-hydroxypyrrolidine-2,5-dione have been synthesised. The reactivities of these active esters have been determined by studying the kinetics and mechanism of their morpholinolysis in acetonitrile at different temperatures.
Highly efficient one-pot assembly of peptides by double chemoselective coupling
Sampaio-Dias, Ivo E.,Sousa, Carlos A. D.,Silva-Reis, Sara C.,Ribeiro, Sara,García-Mera, Xerardo,Rodríguez-Borges, José E.
supporting information, p. 7533 - 7542 (2017/09/27)
This study describes a methodological advancement in solution-phase peptide synthesis via the development of a convenient and operational protocol to synthesize oligopeptides in a one-pot three-step cascade method, in which two peptide bonds are introduced chemoselectively. Tri- to hexapeptides were obtained in high global yields (80-95%) with virtually no epimerization as determined via HPLC. The methodology described herein represents a faster, easier and milder approach to the synthesis of peptides, and it operates at equimolar amounts. This protocol comprises the formation of secondary and tertiary amides and is compatible with Z, Boc and Fmoc N-protecting groups as well as the use of d/l and non-proteinogenic amino acids.
Importance of π-stacking interactions in the hydrogen atom transfer reactions from activated phenols to short-lived N-oxyl radicals
Mazzonna, Marco,Bietti, Massimo,Dilabio, Gino A.,Lanzalunga, Osvaldo,Salamone, Michela
, p. 5209 - 5218 (2014/06/23)
A kinetic study of the hydrogen atom transfer from activated phenols (2,6-dimethyl- and 2,6-di-tert-butyl-4-substituted phenols, 2,2,5,7,8- pentamethylchroman-6-ol, caffeic acid, and (+)-cathechin) to a series of N-oxyl radical (4-substituted phthalimide-N-oxyl radicals (4-X-PINO), 6-substituted benzotriazole-N-oxyl radicals (6-Y-BTNO), 3-quinazolin-4-one-N-oxyl radical (QONO), and 3-benzotriazin-4-one-N-oxyl radical (BONO)), was carried out by laser flash photolysis in CH3CN. A significant effect of the N-oxyl radical structure on the hydrogen transfer rate constants (kH) was observed with kH values that monotonically increase with increasing NO-H bond dissociation energy (BDENO-H) of the N-hydroxylamines. The analysis of the kinetic data coupled to the results of theoretical calculations indicates that these reactions proceed by a hydrogen atom transfer (HAT) mechanism where the N-oxyl radical and the phenolic aromatic rings adopt a π-stacked arrangement. Theoretical calculations also showed pronounced structural effects of the N-oxyl radicals on the charge transfer occurring in the π-stacked conformation. Comparison of the kH values measured in this study with those previously reported for hydrogen atom transfer to the cumylperoxyl radical indicates that 6-CH3-BTNO is the best N-oxyl radical to be used as a model for evaluating the radical scavenging ability of phenolic antioxidants.