2-Amino-5-bromo-3-pyridinol

Name: 2-Amino-5-bromo-3-pyridinol
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 39903-01-0
Cat. No. CS-D1535
Purity≥97%
MDL No.MFCD09744143

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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+
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Structure of 39903-01-0

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General Information

CAS No. 39903-01-0
Cat. No. CS-D1535
Purity ≥97%
MDL No. MFCD09744143
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₅BrN₂O
Molecular Weight 189.01
Synonym(s) 2-Amino-3-hydroxy-5-bromopyridine; 2-Amino-5-bromo-3-hydroxypyridine; 5-Bromo-3-hydroxy-2-aminopyridine; 2-Hydroxy-3-Amino-5-Bromo Pyridine
SMILES OC1=CC(Br)=CN=C1N

Description

2-Amino-5-bromo-3-pyridinol features a brominated pyridinol core with complementary amino and hydroxyl functionalities, enabling direct incorporation into heterocyclic scaffolds. This bench-stable derivative serves as a key building block for bioactive molecules in medicinal chemistry and materials science.

Application

2-Amino-5-bromo-3-pyridinol serves as a versatile building block for heterocyclic synthesis, enabling efficient access to functionalized pyridine scaffolds. Its orthogonal reactivity—combining a nucleophilic amino group with a readily displaced bromide—facilitates palladium-catalyzed cross-coupling and electrophilic substitution reactions. The compound exhibits excellent bench stability and is compatible with standard purification protocols, making it well-suited for medicinal chemistry campaigns and process-scale applications.

Synthesis

Route1
- In-stock
  
  21594-52-5
- ~10%
- In-stock
  
  39903-01-0
References
- PFIZER INC. Patent: WO2006/21886 A1, 2006 ; Location in patent: Page/Page column 64; 65 ; WO 2006/021886 A1
Route2
- In-stock
  
  16867-03-1
- ~%
- In-stock
  
  39903-01-0
References
- Tatipaka, Hari Babu; Gillespie, J. Robert; Chatterjee, Arnab K.; Norcross, Neil R.; Hulverson, Matthew A.; Ranade, Ranae M.; Nagendar, Pendem; Creason, Sharon A.; McQueen, Joshua; Duster, Nicole A.; Nagle, Advait; Supek, Frantisek; Molteni, Valentina; Wenzler, Tanja; Brun, Reto; Glynne, Richard; Buckner, Frederick S.; Gelb, Michael H. Journal of Medicinal Chemistry, 2014 , vol. 57, # 3 p. 828 - 835
Route3
- In-stock
  
  35486-42-1
- 12775-96-1
- ~%
- In-stock
  
  39903-01-0
References
- Ciba-Geigy Corporation Patent: US4033975 A1, 1977 ;

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-5-bromo-3-pyridinol

CAS No. 39903-01-0

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