1-(Trimethylsilyl)-1H-benzo[d][1,2,3]triazole

Name: 1-(Trimethylsilyl)-1H-benzo[d][1,2,3]triazole
Brand: ChemScene
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CAS No. 43183-36-4
Cat. No. CS-W010721
Purity≥98%
MDL No.MFCD00216577

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FedEx Limited Quantities Ground	$0.00
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1-(Trimethylsilyl)-1H-benzo[d][1,2,3]triazole|CS-W010721

Structure of 43183-36-4

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General Information

CAS No. 43183-36-4
Cat. No. CS-W010721
Purity ≥98%
MDL No. MFCD00216577
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₃N₃Si
Molecular Weight 191.31
Synonym(s) 1-TMS-1H-benzotriazole
SMILES C[Si](N1N=NC2=CC=CC=C21)(C)C

Description

1-(Trimethylsilyl)-1H-benzo[d][1,2,3]triazole serves as a bench-stable, moisture-tolerant triazole reagent that facilitates efficient coupling in late-stage functionalization. This silylated heterocycle integrates readily into synthetic sequences, enabling selective C–H amination and amide bond formation under mild conditions. The trimethylsilyl group enhances solubility and stability while allowing for convenient deprotection.

Application

1-(Trimethylsilyl)-1H-benzo[d][1,2,3]triazole serves as a stable, bench-friendly silyl protecting group for azide functionality, enabling selective N-acylation and subsequent desilylation under mild conditions. It functions as a key building block in the synthesis of triazole-based scaffolds, offering excellent compatibility with diverse functional groups and facilitating efficient coupling reactions in peptide and small-molecule synthesis.

Synthesis

Route1
- 95-14-7
- 999-97-3
- ~95%
- In-stock
  
  43183-36-4
References
- Sheludyakov, V. D.; Sheludyakova, S. V.; Kuznetsova, M. G.; Silkina, N. N.; Mironov, V. F. J. Gen. Chem. USSR (Engl. Transl.), 1980 , vol. 50, # 4 p. 875 - 881,705 - 711
Route2
- 95-14-7
- 10416-59-8
- ~%
- In-stock
  
  43183-36-4
References
- Boto, Alicia; Hernandez, Dacil; Hernandez, Rosendo European Journal of Organic Chemistry, 2010 , # 20 p. 3847 - 3857
Route3
- In-stock
  
  51-17-2
- 75-77-4
- ~%
- In-stock
  
  43183-36-4
References
- Yavorskii, A. E.; Stetsenko, A. V.; Zavgorodnii, S. G.; Florent'ev, V. L. Chemistry of Heterocyclic Compounds (New York, NY, United States), 1988 , vol. 24, p. 163 - 167 Khimiya Geterotsiklicheskikh Soedinenii, 1988 , vol. 24, # 2 p. 198 - 202

Safety Information

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GHS Pictogram :	GHS No : GHS02,GHS07
Signal Word : Danger	UN#: 1993
Class : 3	Packing Group : Ⅱ
Hazard Statements : H225-H315-H319-H335
Precautionary Statements : P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

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Computational Chemistry Data

TPSA 30.71
LogP 2.1143
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Organosilicon compounds

Material Science Organic-Inorganic Hybrid Materials A silane coupling agent

Building Blocks Skeleton Aromatic heterocycle compounds Triazole compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Synthetic Reagents Protection, Deprotection, Derivatization Protecting and Derivatizing Reagents

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1-(Trimethylsilyl)-1H-benzo[d][1,2,3]triazole

CAS No. 43183-36-4

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