3-Bromo-1H-pyrazolo[3,4-b]pyridine

Name: 3-Bromo-1H-pyrazolo[3,4-b]pyridine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 68618-36-0
Cat. No. CS-W010552
Purity≥98%
MDL No.MFCD08669476

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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3-Bromo-1H-pyrazolo[3,4-b]pyridine|CS-W010552

Structure of 68618-36-0

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General Information

CAS No. 68618-36-0
Cat. No. CS-W010552
Purity ≥98%
MDL No. MFCD08669476
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrN₃
Molecular Weight 198.02
Synonym(s) 1H-PYRAZOLO[3,4-B]PYRIDINE, 3-BROMO-
SMILES BrC1=NNC2=C1C=CC=N2

Description

3-Bromo-1H-pyrazolo[3,4-b]pyridine features a fused heterocyclic core with a bromine substituent at the 3-position, enabling direct functionalization in cross-coupling reactions. This electron-deficient scaffold integrates readily into pharmaceutical and agrochemical discovery pipelines, offering high reactivity under standard palladium-catalyzed conditions.

Application

3-Bromo-1H-pyrazolo[3,4-b]pyridine serves as a versatile building block for heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions with high efficiency. The bromo group facilitates reliable functionalization in Suzuki, Stille, and Negishi transformations, while the fused pyrazolo-pyridine core provides inherent stability and favorable electronic properties for medicinal chemistry applications. This compound exhibits excellent bench stability and simplifies purification, making it well-suited for iterative synthesis of complex nitrogen-containing scaffolds.

Synthesis

Route1
- In-stock
  
  271-73-8
- ~85%
- In-stock
  
  68618-36-0
References
- ARRAY BIOPHARMA INC.; GENENTECH, INC.; AHRENDT, Kateri A.; BUCKMELTER, Alexandre J.; DE MEESE, Jason; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen R.; LUNGHOFER, Paul; MORENO, David; NEWHOUSE, Brad; REN, Li; SEO, Jeongbeob; TIAN, Hongqi; WENGLOWSKY, Steven Mark; FENG, Bainian; GUNZNER, Janet; MALESKY, Kim; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; YOUNG, Wendy B. Patent: WO2009/111279 A1, 2009 ; Location in patent: Page/Page column 81 ; WO 2009/111279 A1
Route2
- 63682-42-8
- ~90%
- In-stock
  
  68618-36-0
References
- Kocevar, Marijan; Stanovnik, Branko; Tisler, Miha Monatshefte fuer Chemie, 1988 , vol. 119, p. 597 - 604
Route3
- In-stock
  
  36404-88-3
- ~%
- In-stock
  
  68618-36-0
References
- Canadian Journal of Chemistry, , vol. 66, # 3 p. 420-428

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
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 41.57
LogP 1.7204
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Key Words

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3-Bromo-1H-pyrazolo[3,4-b]pyridine

CAS No. 68618-36-0

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