Lot numbers can be found on the outside label of a product:
tert-Butyl 5-bromonicotinate
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CAS No. 263270-02-6
- Cat. No. CS-0130061
- Purity≥98%
- MDL No.MFCD07367903
*For research and further manufacturing use only, not for direct human use.
Structure of 263270-02-6
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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
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.
Synthesis
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Route1
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20826-04-4 -
In-stock
24424-99-5 - ~96%
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In-stock
263270-02-6
References
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Wright, Stephen W. Journal of Heterocyclic Chemistry, 2012 , vol. 49, # 2 p. 442 - 445
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Route2
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20826-04-4
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75-65-0 - ~%
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In-stock
263270-02-6
References
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MERCK and CO., INC.; BANYU PHARMACEUTICAL CO., LTD. Patent: WO2008/88692 A2, 2008 ; Location in patent: Page/Page column 105 ;
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Route3
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20826-04-4
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67098-46-8
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In-stock
263270-02-6
References
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Tanaka, Taisaku; Sugawara, Hajime; Maruoka, Hiroshi; Imajo, Seiichi; Muto, Tsuyoshi Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 14 p. 4233 - 4249
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302
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Precautionary Statements : P264-P270-P330
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Quality Control
Computational Chemistry Data
- TPSA 39.19
- LogP 2.7994
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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