Lot numbers can be found on the outside label of a product:
3-(Methyl(phenyl)amino)acrylaldehyde
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CAS No. 14189-82-3
- Cat. No. CS-0188131
- Purity≥98%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 14189-82-3
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General Information
- CAS No. 14189-82-3
- Cat. No. CS-0188131
- Purity ≥98%
- MDL No. None
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₁₁NO
- Molecular Weight 161.20
- Synonym(s) 3-N-METHYL-N-PHENYLAMINOACROLEINI
- SMILES CN(C=CC=O)C1=CC=CC=C1
Description
3-(Methyl(phenyl)amino)acrylaldehyde is a reactive enal featuring a conjugated system that enables efficient coupling in synthetic transformations. The electron-rich amino group enhances nucleophilicity, while the aldehyde functionality supports selective derivatization under mild conditions. This compound integrates readily into complex molecular architectures requiring controlled reactivity and spatial orientation.
Application
3-(Methyl(phenyl)amino)acrylaldehyde serves as a versatile α,β-unsaturated aldehyde building block for the synthesis of substituted pyridines, quinolines, and other heterocyclic scaffolds via condensation or cycloaddition reactions. Its conjugated enal system enables efficient Michael additions and Pictet–Spengler-type cyclizations, while the N-methyl-N-phenylamino group provides moderate electronic stabilization and favorable solubility in common organic solvents. The compound exhibits sufficient bench stability for routine handling and purification by flash chromatography, making it suitable for iterative synthetic sequences in medicinal chemistry and process development workflows.
Synthesis
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Route1
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624-67-9 -
100-61-8
- ~84%
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In-stock
14189-82-3
References
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RANBAXY LABORATORIES LIMITED Patent: WO2006/90256 A1, 2006 ; Location in patent: Page/Page column 11-12 ;
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Route2
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107-02-8
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100-61-8
- ~88%
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In-stock
14189-82-3
References
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Jin, Xiongjie; Yamaguchi, Kazuya; Mizuno, Noritaka Angewandte Chemie - International Edition, 2014 , vol. 53, # 2 p. 455 - 458 Angew. Chem., 2014 , vol. 126, # 2 p. 465 - 468,4
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Route3
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111-34-2
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93-61-8
- ~91%
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In-stock
14189-82-3
References
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Zacharia, James T.; Tanaka, Takanori; Hayashi, Masahiko Journal of Organic Chemistry, 2010 , vol. 75, # 22 p. 7514 - 7518
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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-P330-P362+P364-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 20.31
- LogP 1.8354
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 3
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Key Words
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