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Sigma-Aldrich

1-Hydroxybenzotriazole hydrate

wetted with not less than 20 wt. % water, 97% dry basis

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Synonym(s):
HOBt Hydrate
Empirical Formula (Hill Notation):
C6H5N3O · xH2O
CAS Number:
123333-53-9
Molecular Weight:
135.12 (anhydrous basis)
Beilstein:
4515
EC Number:
219-989-7
PubChem Substance ID:
329763060
NACRES:
NA.22

Quality Level

200

Assay

97% dry basis

form

powder

quality

wetted with not less than 20 wt. % water

composition

Water content, ~20%

reaction suitability

reaction type: Addition Reactions

mp

155-158 °C (lit.)

solubility

DMF: 0.1 g/mL, clear

SMILES string

[H]O[H].On1nnc2ccccc12

InChI

1S/C6H5N3O.H2O/c10-9-6-4-2-1-3-5(6)7-8-9;/h1-4,10H;1H2

InChI key

PJUPKRYGDFTMTM-UHFFFAOYSA-N

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General description

1-Hydroxybenzotriazolehydrate (HOBt hydrate) is a hydrated form of HOBt. HOBt is a nucleophilic additive commonly used in synthetic chemistry. It is widely employed as acatalyst or stoichiometric additive to accelerate nucleophilic acyl substitution reactions, specifically amidations. Additionally, it is also used in the synthesis of peptides and nucleotides.

Application

1-Hydroxybenzotriazole hydrate is used as an additive:
  • In the oligonucleotide couplings.
  • In the preparation of poly(ethylene glycol)methyl ether-grafted CTS (mPEG-g-CTS).
1-Hydroxybenzotriazole hydrate can also be used:
  • In the solid phase peptide synthesis on TCNEO(tetracyanoethylene oxide)-modified graphite.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H207 - H319 - H412

Hazard Classifications

Aquatic Chronic 3 - Desen. Expl. 2 - Eye Irrit. 2

Storage Class Code

4.1A - Other explosive hazardous materials

WGK

WGK 1

Flash Point(F)

314.6 °F

Flash Point(C)

157 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synlett, 733-733 (1993)
T Katoh et al.
International journal of peptide and protein research, 42(3), 264-269 (1993-09-01)
3-Dimethylphosphinothioyl-2(3H)-oxazolone (MPTO) was synthesized, and its ability to effect racemization-free couplings and cyclization of a peptide and its C-terminal epimer was examined. MPTO showed good reactivity in aprotic polar solvents such as N,N-dimethylformamide (DMF) and N-methylpyrrolidone. In reactivity MPTO resembles
Tetrahedron Letters, 34, 6383-6383 (1993)
Tetrahedron Letters, 35, 3315-3315 (1994)
Injectable gel scaffold based on biopolymer microspheres via an enzymatic reaction.
Huaping Tan et al.
Advanced healthcare materials, 3(11), 1769-1775 (2014-05-17)
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