2-Amino-6-bromopyridin-3-ol

Name: 2-Amino-6-bromopyridin-3-ol
Brand: ChemScene
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CAS No. 934758-27-7
Cat. No. CS-W005713
Purity≥95%
MDL No.MFCD11110242

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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+
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General Information

CAS No. 934758-27-7
Cat. No. CS-W005713
Purity ≥95%
MDL No. MFCD11110242
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₅BrN₂O
Molecular Weight 189.01
Synonym(s) 2-Amino-6-bromo-3-hydroxypyridine
SMILES NC1=NC(Br)=CC=C1O

Description

2-Amino-6-bromopyridin-3-ol features a bromine substituent at the 6-position and a hydroxyl group at the 3-position of the pyridine core, enabling direct functionalization in cross-coupling reactions. The amino group enhances nucleophilicity, while the electron-deficient ring facilitates palladium-catalyzed transformations. This scaffold offers high reactivity under standard conditions and demonstrates stability during handling.

Application

2-Amino-6-bromopyridin-3-ol serves as a versatile building block in medicinal chemistry, enabling efficient access to substituted pyridine scaffolds via Pd-catalyzed cross-coupling and electrophilic substitution reactions. Its dual amino and hydroxyl functionalities offer orthogonal reactivity for sequential derivatization, while the bromine atom provides a reliable handle for C–C bond formation. The compound exhibits good bench stability and is readily purified by recrystallization, facilitating its use in high-throughput synthesis of API candidates and functionalized heterocycles.

Synthesis

Route1
- In-stock
  
  443956-08-9
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- In-stock
  
  934758-27-7
References
- O'Donnell, Christopher J.; Rogers, Bruce N.; Bronk, Brian S.; Bryce, Dianne K.; Coe, Jotham W.; Cook, Karen K.; Duplantier, Allen J.; Evrard, Edelweiss; Hajos, Mihaly; Hoffmann, William E.; Hurst, Raymond S.; Maklad, Noha; Mather, Robert J.; McLean, Stafford; Nedza, Frank M.; O'Neill, Brian T.; Peng, Langu; Qian, Weimin; Rottas, Melinda M.; Sands, Steven B.; Schmidt, Anne W.; Shrikhande, Alka V.; Spracklin, Douglas K.; Wong, Diane F.; Zhang, Andy; Zhang, Lei Journal of Medicinal Chemistry, 2010 , vol. 53, # 3 p. 1222 - 1237

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 59.14
LogP 1.1319
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Amino-6-bromopyridin-3-ol

CAS No. 934758-27-7

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