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Merck
CN

440051

Sigma-Aldrich

1-(Chloromethyl)-1H-benzotriazole

98%

Synonym(s):

1-(Chloromethyl)benzotriazole

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About This Item

Empirical Formula (Hill Notation):
C7H6ClN3
CAS Number:
Molecular Weight:
167.60
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Assay

98%

reaction suitability

reaction type: C-C Bond Formation

mp

136-139 °C (lit.)

functional group

chloro

SMILES string

ClCn1nnc2ccccc12

InChI

1S/C7H6ClN3/c8-5-11-7-4-2-1-3-6(7)9-10-11/h1-4H,5H2

InChI key

VSEROABGEVRIRY-UHFFFAOYSA-N

Application

1-(Chloromethyl)-1H-benzotriazole can be used as a reactant:
  • In Gewald cyclocondensation reactions.
  • To prepare N-(benzotriazol-1-ylmethyl) heterocycles by reacting with nitrogen heterocycles.
  • To synthesize palladium complexes for applications in Heck and Suzuki-Miyaura C-C coupling reactions.
  • In the synthesis of 2,3-disubstituted benzofurans by treating with o-hydroxyphenyl ketones.

Reactant for preparation of:
  • Palladium complexes for applications in Heck coupling reactions
  • Bacterial peptide deformylase (PDF) inhibitors
  • Nonpeptide inhibitors of Human Mast Cell Chymase

  • Reactant for Gewald cyclocondensation reactions

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Novel syntheses of 2, 3-disubstituted benzofurans
Katritzky AR, et al.
The Journal of Organic Chemistry, 66(16), 5613-5615 (2001)
Palladium and half sandwich ruthenium (II) complexes of selenated and tellurated benzotriazoles: synthesis, structural aspects and catalytic applications
D Dipanwita, et al.
Journal of Organometallic Chemistry, 695(7), 955-962 (2010)
Preparation, lithiation and transformation of N-(benzotriazol-1-ylmethyl) heterocycles
Katritzky AR, et al.
Journal of Heterocyclic Chemistry, 26(3), 829-836 (1989)
Modification of the Gewald methodology for the synthesis of 3-amino-2-(1H-1, 2, 3-benzotriazol-1-yl) substituted benzofurans, benzothiophenes and 1H-indoles
Radl, S, et al.
ARKIVOC (Gainesville, FL, United States), 15, 4-11 (2005)

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