Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

440051

Sigma-Aldrich

1-(Chloromethyl)-1H-benzotriazole

98%

Synonym(s):

1-(Chloromethyl)benzotriazole

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C7H6ClN3
CAS Number:
54187-96-1
Molecular Weight:
167.60
MDL number:
MFCD00216649
UNSPSC Code:
12352005
PubChem Substance ID:
24867562
NACRES:
NA.22

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.[1]
  • To prepare N-(benzotriazol-1-ylmethyl) heterocycles by reacting with nitrogen heterocycles.[2]
  • To synthesize palladium complexes for applications in Heck and Suzuki-Miyaura C-C coupling reactions.[3]
  • In the synthesis of 2,3-disubstituted benzofurans by treating with o-hydroxyphenyl ketones.[4]

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
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
05822BJ
12316TC
13927DS
13220EU
24431MO

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Novel syntheses of 2, 3-disubstituted benzofurans
Katritzky AR, et al.
The Journal of Organic Chemistry, 66(16), 5613-5615 (2001)
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)

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service