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Key Documents

B11400

Sigma-Aldrich

Benzotriazole

ReagentPlus®, 99%

Synonym(s):

1,2,3-Benzotriazole, 1H-Benzotriazole

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About This Item

Empirical Formula (Hill Notation):
C6H5N3
CAS Number:
Molecular Weight:
119.12
Beilstein/REAXYS Number:
112133
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

vapor density

4.1 (vs air)

Quality Level

vapor pressure

0.04 mmHg ( 20 °C)

product line

ReagentPlus®

assay

99%

form

powder

mp

97-99 °C (lit.)

SMILES string

c1ccc2[nH]nnc2c1

InChI

1S/C6H5N3/c1-2-4-6-5(3-1)7-9-8-6/h1-4H,(H,7,8,9)

InChI key

QRUDEWIWKLJBPS-UHFFFAOYSA-N

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General description

Benzotriazole is used as a synthetic auxiliary for the preparation of organic derivatives and as a corrosion inhibitors for Cu and its alloys.

Application

Benzotriazole can be used as a reactant to synthesize:
  • β-Aminocarbonyl compounds via Mannich reaction of secondary amines and aldehydes in the presence of p-toluenesulfonic acid as a catalyst.
  • Acylbenzotriazoles via thionyl chloride catalyzed reaction with nitrobenzoic acids.
  • 1-(2-Pyridyl)benzotriazole by reacting with 2-bromopyridine in the presence of toluene as a solvent.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

338.0 °F - closed cup

flash_point_c

170 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Benzotriazole as a synthetic auxiliary: benzotriazolylalkylations and benzotriazole-mediated heteroalkylation
Alan K R et al.
Synthesis, 1994, 445-456 (1994)
Inhibition of copper corrosion by 1, 2, 3-benzotriazole: a review
Matjavz F et al.
Corrosion Science, 52, 2737-2749 (2010)
Martin Krug et al.
ChemMedChem, 6(1), 63-72 (2010-12-09)
Within the last decade, interest in the development of new anticancer drugs increased mainly from emerging resistance against established drugs, which were found to be limited by the multidrug resistance (MDR) phenomenon. Several anticancer targets have been investigated for the
Derivatization of 1-phenyl substituted 4-amino-2-benzazepin-3-ones: evaluation of Pd-catalyzed coupling reactions
Ballet S, et al.
Tetrahedron, 63, 3718-3727 (2007)
Synthesis, Characterization and Energetic Properties of 1, 3, 4-Oxadiazoles
Wang Z, et al.
European Journal of Organic Chemistry, 2015, 5183-5188 (2015)

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