tert-Butyl 3-bromo-6-chloropicolinate

Name: tert-Butyl 3-bromo-6-chloropicolinate
Brand: ChemScene
Availability: InStock
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CAS No. 1235036-15-3
Cat. No. CS-0021571
Purity≥95%
MDL No.MFCD19443279

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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tert-Butyl 3-bromo-6-chloropicolinate|CS-0021571

Structure of 1235036-15-3

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General Information

CAS No. 1235036-15-3
Cat. No. CS-0021571
Purity ≥95%
MDL No. MFCD19443279
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₁BrClNO₂
Molecular Weight 292.56
Synonym(s) tert-butyl 3-bromo-6-chloropyridine-2-carboxylate
SMILES BrC1=C(C(OC(C)(C)C)=O)N=C(Cl)C=C1

Description

tert-Butyl 3-bromo-6-chloropicolinate features a sterically hindered tert-butyl ester paired with strategically positioned bromo and chloro substituents on the picolinate core. This combination enables direct functionalization in cross-coupling processes, where the electron-deficient pyridine ring facilitates palladium-catalyzed transformations. The molecule exhibits bench-stable handling characteristics and integrates readily into synthetic routes targeting complex heterocyclic architectures.

Application

tert-Butyl 3-bromo-6-chloropicolinate serves as a versatile building block in medicinal chemistry and process development, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The ortho-halogenated pyridine core provides excellent regioselectivity for Suzuki, Stille, and Negishi couplings, while the tert-butyl ester offers bench stability and straightforward deprotection under mild acidic conditions. Its compatibility with diverse functional groups makes it ideal for constructing complex heterocyclic scaffolds and API intermediates.

Synthesis

Route1
- In-stock
  
  929000-66-8
- 75-65-0
- ~97%
- In-stock
  
  1235036-15-3
References
- GENENTECH, INC.; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; ABBOTT LABORATORIES; BAELL, Jonathon, Bayldon; BUI, Chinh, Thien; COLMAN, Peter; CZABOTAR, Peter; DUDLEY, Danette, A.; FAIRBROTHER, Wayne, J.; FLYGARE, John, A.; LASSENE, Guillaume, Laurent; NDUBAKU, Chudi; NIKOLAKOPOULOS, George; SLEEBS, Brad, Edmund; SMITH, Brian, John; WATSON, Keith, Geoffrey; ELMORE, Steven, W.; HASVOLD, Lisa, A.; PETROS, Andrew, M.; SOUERS, Andrew, J.; TAO, Zhi-Fu; WANG, Le; WANG, Xilu; DESHAYES, Kurt Patent: WO2010/80503 A1, 2010 ; Location in patent: Page/Page column 232-233 ; WO 2010/080503 A1

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
Precautionary Statements : P264-P270-P330

Quality Control

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Computational Chemistry Data

TPSA 39.19
LogP 3.4528
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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tert-Butyl 3-bromo-6-chloropicolinate

CAS No. 1235036-15-3

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