6-Azaindole-3-carboxaldehyde

Name: 6-Azaindole-3-carboxaldehyde
Brand: ChemScene
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CAS No. 25957-65-7
Cat. No. CS-W009006
Purity≥96%
MDL No.MFCD08272238

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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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Structure of 25957-65-7

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General Information

CAS No. 25957-65-7
Cat. No. CS-W009006
Purity ≥96%
MDL No. MFCD08272238
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆N₂O
Molecular Weight 146.15
Synonym(s) 1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde
SMILES O=CC1=CNC2=C1C=CN=C2

Description

6-Azaindole-3-carboxaldehyde features a nitrogen-substituted indole core paired with an aldehyde handle at the 3-position, enabling direct incorporation into bioconjugation workflows. The electron-deficient heterocycle enhances reactivity in nucleophilic addition reactions, while the bench-stable aldehyde group tolerates standard handling protocols. This scaffold serves as a key building block for targeted probe synthesis and medicinal chemistry campaigns.

Application

6-Azaindole-3-carboxaldehyde serves as a versatile building block for heterocyclic synthesis, enabling efficient construction of indole-based scaffolds through standard condensation and coupling reactions. The aldehyde functionality facilitates direct functionalization and acts as a key handle in iterative synthesis workflows. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for medicinal chemistry campaigns and process development.

Synthesis

Route1
- In-stock
  
  271-29-4
- 4885-02-3
- ~%
- In-stock
  
  25957-65-7
References
- KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothée; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim Patent: WO2013/45516 A1, 2013 ; Location in patent: Page/Page column 200 ;
Route2
- In-stock
  
  271-29-4
- 100-97-0
- ~32%
- In-stock
  
  25957-65-7
References
- Nakano, Hirofumi; Saito, Nae; Parker, Lorien; Tada, Yukio; Abe, Masanao; Tsuganezawa, Keiko; Yokoyama, Shigeyuki; Tanaka, Akiko; Kojima, Hirotatsu; Okabe, Takayoshi; Nagano, Tetsuo Journal of Medicinal Chemistry, 2012 , vol. 55, # 11 p. 5151 - 5164

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 45.75
LogP 1.3754
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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6-Azaindole-3-carboxaldehyde

CAS No. 25957-65-7

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