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7-(Diethylamino)-2-oxo-2H-chromene-3-carbaldehyde
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CAS No. 57597-64-5
- Cat. No. CS-0127686
- Purity≥98%
- MDL No.MFCD00438856
*For research and further manufacturing use only, not for direct human use.
Structure of 57597-64-5
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General Information
- CAS No. 57597-64-5
- Cat. No. CS-0127686
- Purity ≥98%
- MDL No. MFCD00438856
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₄H₁₅NO₃
- Molecular Weight 245.27
- Synonym(s) 7-N,N-diethylaminocoumarin-3-carboxaldehyde
- SMILES O=CC1=CC2=CC=C(N(CC)CC)C=C2OC1=O
Description
7-(Diethylamino)-2-oxo-2H-chromene-3-carbaldehyde features a conjugated chromenone core with a diethylamino group enhancing electron density at the C7 position and a formyl group at C3 enabling nucleophilic addition. This scaffold integrates readily into synthetic routes for fluorescent probes and photoactive materials, offering tunable photophysical properties under standard conditions.
Application
7-(Diethylamino)-2-oxo-2H-chromene-3-carbaldehyde serves as a versatile building block in the synthesis of fused heterocycles and bioactive scaffolds. Its conjugated aldehyde and enone functionality enables efficient Michael additions, aldol condensations, and Pechmann-type cyclizations. The diethylamino group enhances electron density at the chromenone core, facilitating nucleophilic transformations while maintaining bench stability and ease of purification under standard organic protocols.
Synthesis
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Route1
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In-stock
20571-42-0 -
68-12-2 - ~77%
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In-stock
57597-64-5
References
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Lacivita, Enza; Masotti, Anna Carmela; Jafurulla, Md.; Saxena, Roopali; Rangaraj, Nandini; Chattopadhyay, Amitabha; Colabufo, Nicola A.; Berardi, Francesco; Perrone, Roberto; Leopoldo, Marcello Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 22 p. 6628 - 6632
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Route2
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In-stock
20571-42-0
- ~%
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In-stock
57597-64-5
References
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Bayer Aktiengesellschaft Patent: US4018796 A1, 1977 ;
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Route3
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In-stock
17754-90-4 - ~%
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In-stock
57597-64-5
References
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Padmanabhan; Peri; Triggle Synthetic Communications, 1996 , vol. 26, # 4 p. 827 - 831
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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-P280-P302+P352
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Quality Control
Computational Chemistry Data
- TPSA 50.52
- LogP 2.4517
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 4
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Key Words
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