tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Name: tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 942070-45-3
Cat. No. CS-W005740
Purity≥97%
MDL No.None

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tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate|CS-W005740

Structure of 942070-45-3

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General Information

CAS No. 942070-45-3
Cat. No. CS-W005740
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₉H₂₆BNO₄
Molecular Weight 343.23
Synonym(s) tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate
SMILES O=C(N1C=C(B2OC(C)(C)C(C)(C)O2)C3=C1C=CC=C3)OC(C)(C)C

Description

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate delivers a stable, bench-ready boronate handle for Suzuki-Miyaura cross-coupling. The tetramethyl-substituted dioxaborolane enhances reactivity and shelf stability, while the indole scaffold supports direct functionalization in complex molecule assembly.

Application

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate serves as a stable, bench-ready boron building block for palladium-catalyzed cross-coupling reactions. The indole core enables efficient access to functionalized heterocyclic scaffolds, while the Bpin group facilitates reliable Suzuki-Miyaura coupling under mild conditions. Its tert-butyl ester functionality offers orthogonal protection and simplifies purification, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

Route1
- 61676-62-8
- In-stock
  
  192189-07-4
- ~56%
- In-stock
  
  942070-45-3
References
- Watson, Charlotte G.; Aggarwal, Varinder K. Organic Letters, 2013 , vol. 15, # 6 p. 1346 - 1349
Route2
- 120-72-9
- ~%
- In-stock
  
  942070-45-3
References
- European Journal of Organic Chemistry, , # 24 p. 4532 - 4535
Route3
- In-stock
  
  192189-07-4
- 25015-63-8
- ~%
- In-stock
  
  942070-45-3
References
- Organic and Biomolecular Chemistry, , vol. 9, # 9 p. 3139 - 3141

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 49.69
LogP 3.7237
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

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tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

CAS No. 942070-45-3

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