Imidazo[1,5-a]pyridine-6-carboxylic acid

Name: Imidazo[1,5-a]pyridine-6-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 256935-76-9
Cat. No. CS-W005633
Purity≥95%
MDL No.MFCD11042992

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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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Imidazo[1,5-a]pyridine-6-carboxylic acid|CS-W005633

Structure of 256935-76-9

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General Information

CAS No. 256935-76-9
Cat. No. CS-W005633
Purity ≥95%
MDL No. MFCD11042992
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆N₂O₂
Molecular Weight 162.15
Synonym(s) Imidazo[1,5-a]pyridine-6-carboxylic acid (9CI)
SMILES O=C(C1=CN2C(C=C1)=CN=C2)O

Description

Imidazo[1,5-a]pyridine-6-carboxylic acid features a fused heterocyclic core with a carboxylic acid group at the 6-position, enabling direct conjugation or derivatization. This scaffold combines enhanced planarity and electron-deficient character, facilitating integration into bioactive molecules. The functional group supports efficient coupling reactions under standard conditions, making it valuable for medicinal chemistry and materials development.

Application

Imidazo[1,5-a]pyridine-6-carboxylic acid serves as a versatile heterocyclic building block in medicinal chemistry, enabling the construction of bioactive scaffolds through standard amide coupling and derivatization protocols. Its carboxylic acid functionality facilitates direct conjugation with amines, while the fused imidazopyridine core exhibits favorable stability and solubility for downstream synthetic transformations. This compound functions as a key intermediate in the development of kinase inhibitors and other targeted therapeutics, offering robust compatibility with common reaction conditions and purification methods.

Synthesis

Route1
- 139183-89-4
- ~83%
- In-stock
  
  256935-76-9
References
- Li, Qun; Woods, Keith W.; Claiborne, Akiyo; Gwaltney, Ii, Stephen L.; Barr, Kenneth J.; Liu, Gang; Gehrke, Laura; Credo; Hui, Yu Hua; Lee, Jang; Warner, Robert B.; Kovar, Peter; Nukkala, Michael A.; Zielinski, Nicolette A.; Tahir, Stephen K.; Fitzgerald, Michael; Kim, Ki H.; Marsh, Kennan; Frost, David; Ng, Shi-Chung; Rosenberg, Saul; Sham, Hing L. Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 3 p. 465 - 469
Route2
- 139183-88-3
- ~%
- In-stock
  
  256935-76-9
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 12, # 3 p. 465 - 469

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

Quality Control

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Computational Chemistry Data

TPSA 54.6
LogP 1.0325
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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Imidazo[1,5-a]pyridine-6-carboxylic acid

CAS No. 256935-76-9

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