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

Name: 2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole
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CAS No. 1402166-32-8
Cat. No. CS-0153832
Molecule weight289.99
Purity≥97%
MDL No.MFCD13181957

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2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole|CS-0153832

Structure of 1402166-32-8

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General Information

CAS No. 1402166-32-8
Cat. No. CS-0153832
Purity ≥97%
MDL No. MFCD13181957
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₃BBrNO₂S
Molecular Weight 289.99
Synonym(s) 2-Bromothiazole-5-boronic acid pinacol ester
SMILES CC1(C)C(C)(C)OB(C2=CN=C(Br)S2)O1

Description

This boronate-functional thiazole integrates seamlessly into Suzuki-Miyaura cross-coupling reactions under standard conditions. The tetramethyl-1,3,2-dioxaborolane moiety enhances stability and reactivity, while the bromine substituent enables orthogonal functionalization. Bench-stable and moisture-tolerant, this compound streamlines access to complex heteroaromatic architectures in medicinal chemistry and materials science.

Application

2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole serves as a versatile Suzuki-Miyaura coupling building block, enabling efficient C–C bond formation under mild conditions. The boronate ester group exhibits excellent stability, facilitates straightforward purification, and tolerates a range of functional groups. Its thiazole core provides a rigid, electron-deficient heterocyclic scaffold commonly found in bioactive molecules, making it well-suited for medicinal chemistry and materials science applications.

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-P280-P302+P352

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Computational Chemistry Data

TPSA 31.35
LogP 2.2048
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Thiazole compounds

Key Words

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

CAS No. 1402166-32-8

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