2592-95-2 Usage
Chemical Properties
white to light yellow powder
Uses
1-Hydroxybenzotriazole (HOBT) is used in preparation method of carbon fiber/polyamide composite powder material for laser sintering.
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.
ULTRAVIOLET RADIATION ABSORBING POLYETHERS
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Page/Page column, (2014/02/15)
A polymer composition comprising a linear ultraviolet radiation absorbing polyether that comprises a chemically bound UV-chromophore.
