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Hydroxybenzotriazole information


Hydroxybenzotriazole
Hydroxybenzotriazole
Space-filling model of the hydroxybenzotriazole molecule
Names
Preferred IUPAC name
1H-1,2,3-Benzotriazol-1-ol
Other names
N-Hydroxybenzotriazole
HOBt
Identifiers
CAS Number
  • 2592-95-2 checkY
  • (monohydrate): 80029-43-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 68282 checkY
ECHA InfoCard 100.018.173 Edit this at Wikidata
EC Number
  • 219-989-7
  • (monohydrate): 602-929-2
PubChem CID
  • 75771
  • (monohydrate): 2796029
UNII
  • A2T929DMG4 checkY
  • (monohydrate): S72K7GY45F checkY
CompTox Dashboard (EPA)
  • DTXSID3044627 Edit this at Wikidata
InChI
  • InChI=1S/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H checkY
    Key: ASOKPJOREAFHNY-UHFFFAOYSA-N ☒N
  • InChI=1/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H
    Key: ASOKPJOREAFHNY-UHFFFAOYAP
SMILES
  • n1nn(O)c2ccccc12
Properties
Chemical formula
C6H5N3O
Molar mass 135.1234 g mol−1 (anhydrous)
Melting point 156 to 159 °C (313 to 318 °F; 429 to 432 K) (decomposes)
Hazards
GHS labelling:
Pictograms
GHS01: Explosive
Signal word
Danger
Hazard statements
H203
Precautionary statements
P210, P230, P240, P250, P280, P370+P380, P372, P373, P401, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Hydroxybenzotriazole (abbreviated HOBt) is an organic compound that is a derivative of benzotriazole. It is a white crystalline powder, which as a commercial product contains some water (~11.7% wt as the HOBt monohydrate crystal). Anhydrous HOBt is explosive.

It is mainly used to suppress the racemization of single-enantiomer chiral molecules and to improve the efficiency of peptide synthesis.

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Hydroxybenzotriazole

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Hydroxybenzotriazole (abbreviated HOBt) is an organic compound that is a derivative of benzotriazole. It is a white crystalline powder, which as a commercial...

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Steglich esterification

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formation of amides by means of DCC (dicyclohexylcarbodiimide) and 1-hydroxybenzotriazole (HOBT). This reaction generally takes place at room temperature....

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Tolyltriazole

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has better solubility in some organic solvents.[citation needed] Hydroxybenzotriazole Wikimedia Commons has media related to Benzotriazoles. Benzotriazole...

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HBTU

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salts. HBTU activates carboxylic acids by forming a stabilized HOBt (Hydroxybenzotriazole) leaving group. The activated intermediate species attacked by the...

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Dichloromethane

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DMAP, react with DCM to form methylene bispyridinium dichlorides. Hydroxybenzotriazole and related reagents used in peptide coupling react with DCM in the...

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Carbodiimide

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convert carboxylic acids to amides or esters. Additives, such as N-hydroxybenzotriazole or N-hydroxysuccinimide, are often added to increase yields and decrease...

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Active ester

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are often used in peptide synthesis, e.g., N-hydroxysuccinimide, hydroxybenzotriazole. Active esters of acrylic acid are precursors to polymers with reactive...

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List of UN numbers 3401 to 3500

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packed with equipment, containing flammable liquids UN 3474 4.1 1-Hydroxybenzotriazole, anhydrous, wetted with not less than 20% water, by mass UN 3475...

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List of UN numbers 0501 to 0600

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Signals, distress, ship UN 0507 1.4S Signals, smoke UN 0508 1.3C 1-Hydroxybenzotriazole, anhydrous, dry or wetted with less than 20% water, by mass UN 0509...

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Ethyl cyanohydroxyiminoacetate

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or ethyl acetate. Compared with the benzotriazole derivatives 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) (which are widely...

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Weinreb ketone synthesis

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Weinreb–Nahm amides from carboxylic acids. Various carbodiimide-, hydroxybenzotriazole-, and triphenylphosphine-based couplings have been reported specifically...

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