7-(Benzyloxy)-1H-indole-3-carbaldehyde

Name: 7-(Benzyloxy)-1H-indole-3-carbaldehyde
Brand: ChemScene
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CAS No. 92855-65-7
Cat. No. CS-W008442
Purity≥98%
MDL No.MFCD00055979

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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+
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7-(Benzyloxy)-1H-indole-3-carbaldehyde|CS-W008442

Structure of 92855-65-7

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General Information

CAS No. 92855-65-7
Cat. No. CS-W008442
Purity ≥98%
MDL No. MFCD00055979
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₁₃NO₂
Molecular Weight 251.28
Synonym(s) 7-Benzyloxyindole-3-carbaldehyde
SMILES O=CC1=CNC2=C1C=CC=C2OCC3=CC=CC=C3

Description

7-(Benzyloxy)-1H-indole-3-carbaldehyde integrates a benzyl ether-stabilized indole scaffold with a reactive aldehyde handle, enabling direct coupling in C–H functionalization and heterocycle synthesis. This bench-stable derivative facilitates efficient access to biologically relevant indole alkaloid analogs under standard conditions.

Application

7-(Benzyloxy)-1H-indole-3-carbaldehyde serves as a versatile building block in medicinal chemistry, enabling efficient access to indole-based scaffolds through standard coupling and functional group transformation protocols. The benzyloxy group provides orthogonal protection for phenolic hydroxyls, while the aldehyde functionality facilitates reductive amination, imine formation, and Mannich reactions. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for iterative synthesis workflows.

Synthesis

Route1
- In-stock
  
  20289-27-4
- 68-12-2
- ~99%
- In-stock
  
  92855-65-7
References
- Fujii, Akihito; Fujima, Yoshito; Harada, Hiroshi; Ikunaka, Masaya; Inoue, Toru; Kato, Shiro; Matsuyama, Keisuke Tetrahedron Asymmetry, 2001 , vol. 12, # 23 p. 3235 - 3240
Route2
- In-stock
  
  20289-27-4
- 100-61-8
- ~65%
- In-stock
  
  92855-65-7
References
- Li, Lan-Tao; Huang, Juan; Li, Hong-Ying; Wen, Li-Juan; Wang, Peng; Wang, Bin Chemical Communications, 2012 , vol. 48, # 42 p. 5187 - 5189

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 42.09
LogP 3.5594
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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7-(Benzyloxy)-1H-indole-3-carbaldehyde

CAS No. 92855-65-7

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