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

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

CAS No. 29274-28-0
Cat. No. CS-W003800
Purity≥97%
MDL No.MFCD11846313

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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+
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4-Chloro-1H-pyrazolo[3,4-b]pyridine|CS-W003800

Structure of 29274-28-0

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General Information

CAS No. 29274-28-0
Cat. No. CS-W003800
Purity ≥97%
MDL No. MFCD11846313
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄ClN₃
Molecular Weight 153.57
Synonym(s) 5-chloro-2,8,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene
SMILES Clc1ccnc2c1cn[nH]2

Description

4-Chloro-1H-pyrazolo[3,4-b]pyridine is a heterocyclic scaffold featuring a chlorinated pyrazolopyridine core, offering enhanced electron-withdrawing character and structural rigidity. This moiety integrates readily into kinase inhibitor architectures and serves as a key building block in medicinal chemistry campaigns targeting purine-binding sites.

Application

4-Chloro-1H-pyrazolo[3,4-b]pyridine serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. Its chlorine substituent facilitates reliable C–H activation and Suzuki-Miyaura coupling, while the fused pyrazolopyridine core provides structural rigidity and favorable pharmacophoric properties for target-directed synthesis. The compound exhibits excellent bench stability and compatibility with common purification methods, making it well-suited for scalable applications in API development and library synthesis.

Synthesis

Route1
- In-stock
  
  924909-17-1
- ~99%
- In-stock
  
  29274-28-0
References
- ARRAY BIOPHARMA INC.; GENENTECH, INC.; DEMEESE, Jason; GAUDINO, John; NEITZEL, Alicia, Tarin; LUNGHOFER, Paul; JEONGBEOB, Seo; HONGQI, Tian; YOUNG, Wendy, B.; SUTHERLIN, Daniel, P. Patent: WO2009/33084 A1, 2009 ; Location in patent: Page/Page column 104 ; WO 2009/033084 A1
Route2
- 924909-12-6
- ~23%
- In-stock
  
  29274-28-0
References
- CHUGAI SEIYAKU KABUSHIKI KAISHA; The University of Tokyo Patent: EP1921078 A1, 2008 ; Location in patent: Page/Page column 33 ; EP 1921078 A1
Route3
- 84054-00-2
- ~%
- In-stock
  
  29274-28-0
References
- Dorn, Helmut; Ozegowski, Ruediger Journal fuer Praktische Chemie (Leipzig), 1982 , vol. 324, # 4 p. 557 - 562

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 41.57
LogP 1.6113
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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4-Chloro-1H-pyrazolo[3,4-b]pyridine

CAS No. 29274-28-0

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