Lot numbers can be found on the outside label of a product:
Methyl 3-formyl-1H-indole-5-carboxylate
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CAS No. 197506-83-5
- Cat. No. CS-W006662
- Purity≥97%
- MDL No.MFCD00211075
*For research and further manufacturing use only, not for direct human use.
Structure of 197506-83-5
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General Information
- CAS No. 197506-83-5
- Cat. No. CS-W006662
- Purity ≥97%
- MDL No. MFCD00211075
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₁H₉NO₃
- Molecular Weight 203.19
- Synonym(s) METHYL 3-FORMYLINDOLE-5-CARBOXYLATE
- SMILES O=C(C1=CC2=C(NC=C2C=O)C=C1)OC
Description
Methyl 3-formyl-1H-indole-5-carboxylate features a dual functional group architecture: an electron-rich indole core paired with a reactive aldehyde at the 3-position and a methyl ester at the 5-position. This arrangement enables direct integration into multicomponent coupling reactions, particularly in transition-metal-catalyzed C–H functionalizations and conjugate additions. The formyl group facilitates nucleophilic attack under mild conditions, while the ester serves as a handle for downstream derivatization. The molecule exhibits bench-stable behavior and is compatible with standard synthetic protocols in medicinal chemistry and natural product synthesis.
Application
Methyl 3-formyl-1H-indole-5-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to biologically relevant indole scaffolds. The orthogonal formyl and ester functionalities facilitate sequential transformations—such as reductive amination, Wittig reactions, and coupling protocols—while maintaining stability under standard bench conditions. Its utility is well-documented in the construction of heterocyclic libraries and API intermediates requiring precise functional group positioning.
Synthesis
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Route1
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In-stock
1011-65-0 -
68-12-2 - ~99%
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In-stock
197506-83-5
References
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Boehringer Ingelheim Pharmaceuticals, Inc. Patent: US2006/276496 A1, 2006 ; Location in patent: Page/Page column 62; 63 ; US 20060276496 A1
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Route2
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In-stock
1011-65-0
- ~89%
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In-stock
197506-83-5
References
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Laboratorios Menarini S.A. Patent: US5990142 A1, 1999 ;
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Route3
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In-stock
1011-65-0
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100-61-8
- ~54%
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In-stock
197506-83-5
References
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Wu, Wenliang; Su, Weiping Journal of the American Chemical Society, 2011 , vol. 133, # 31 p. 11924 - 11927
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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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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Quality Control
Computational Chemistry Data
- TPSA 59.16
- LogP 1.767
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 2
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Key Words
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