5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole

Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole
Brand: ChemScene
Availability: InStock
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CAS No. 1086111-09-2
Cat. No. CS-W006517
Purity≥95%
MDL No.MFCD10697440

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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole|CS-W006517

Structure of 1086111-09-2

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General Information

CAS No. 1086111-09-2
Cat. No. CS-W006517
Purity ≥95%
MDL No. MFCD10697440
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₄BNO₂S
Molecular Weight 211.09
Synonym(s) Thiazole-5-boronic acid pinacol ester
SMILES CC1(C)C(C)(C)OB(C2=CN=CS2)O1

Description

This boronate-functionalized thiazole integrates readily into Suzuki-Miyaura cross-coupling reactions under standard conditions. The tetramethyl-1,3,2-dioxaborolane moiety ensures excellent stability and ease of handling, while the heteroaromatic thiazole core enables direct incorporation into complex molecular architectures.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. Its stable tetramethylboronate group enables efficient coupling with aryl, heteroaryl, and vinyl halides under mild conditions. The thiazole core provides a versatile heterocyclic scaffold for medicinal chemistry and materials science applications. Bench-stable and readily purified by flash chromatography, it facilitates reliable synthesis of complex molecular architectures.

Synthesis

Route1
- In-stock
  
  3034-55-7
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  1086111-09-2
References
- WO2009/151598 A1, ; Page/Page column 167 ; WO 2009/151598 A1
Route2
- In-stock
  
  76-09-5
- In-stock
  
  79265-30-8
- ~70%
- In-stock
  
  1086111-09-2
References
- Primas, Nicolas; Bouillon, Alexandre; Lancelot, Jean-Charles; El-Kashef, Hussein; Rault, Sylvain Tetrahedron, 2009 , vol. 65, # 29-30 p. 5739 - 5746

Safety Information

Download SDS

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

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Computational Chemistry Data

TPSA 31.35
LogP 1.4423
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Thiazole compounds

Key Words

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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole

CAS No. 1086111-09-2

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