tert-Butyl 5-bromonicotinate

Name: tert-Butyl 5-bromonicotinate
Brand: ChemScene
Availability: InStock
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CAS No. 263270-02-6
Cat. No. CS-0130061
Purity≥98%
MDL No.MFCD07367903

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FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Structure of 263270-02-6

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Description

tert-Butyl 5-bromonicotinate features a brominated pyridine ring with a sterically hindered tert-butyl ester, enabling stable coupling in cross-coupling reactions. This bench-stable reagent facilitates direct functionalization of heteroaromatic systems under mild conditions, delivering high yields in palladium-catalyzed transformations.

Application

tert-Butyl 5-bromonicotinate serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization at the C5 position of the pyridine ring. Its bromine substituent facilitates palladium-catalyzed cross-coupling reactions, including Suzuki, Stille, and Negishi couplings, with high efficiency and selectivity. The tert-butyl ester group provides excellent bench stability and compatibility with diverse reaction conditions, allowing straightforward deprotection to the corresponding carboxylic acid under mild acidic conditions. This combination of reactivity and robustness makes it ideal for constructing complex heterocyclic scaffolds and pharmaceutical intermediates.

General Information

CAS No. 263270-02-6
Cat. No. CS-0130061
Purity ≥98%
MDL No. MFCD07367903
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₂BrNO₂
Molecular Weight 258.11
Synonym(s) tert-butyl 5-bromopyridine-3-carboxylate
SMILES O=C(C1=CC(Br)=CN=C1)OC(C)(C)C

Computational Chemistry Data

TPSA 39.19
LogP 2.7994
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

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
Precautionary Statements : P264-P270-P330

Quality Control

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Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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tert-Butyl 5-bromonicotinate

CAS No. 263270-02-6

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