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Ethyl 2,6-dichloroisonicotinate
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CAS No. 1604-14-4
- Cat. No. CS-0037453
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 1604-14-4
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General Information
- CAS No. 1604-14-4
- Cat. No. CS-0037453
- Purity ≥97%
- MDL No. None
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₈H₇Cl₂NO₂
- Molecular Weight 220.05
- Synonym(s) Ethyl 2,6-dichloropyridine-4-carboxylate
- SMILES CCOC(=O)C1=CC(=NC(=C1)Cl)Cl
Description
Ethyl 2,6-dichloroisonicotinate features a pyridine core with strategically positioned chlorine substituents at the 2- and 6-positions, enhancing electrophilic reactivity. This electron-deficient heterocycle integrates readily into synthetic sequences requiring halogen-directed functionalization. The ethyl ester group enables direct manipulation via hydrolysis or nucleophilic substitution. Bench-stable and moisture-tolerant, it serves as a robust building block for pharmaceutical intermediates and agrochemicals.
Application
Ethyl 2,6-dichloroisonicotinate serves as a versatile building block in medicinal chemistry, enabling the synthesis of substituted isonicotinates and heterocyclic scaffolds. Its dual chloro substituents enhance electrophilicity at the ring, facilitating nucleophilic aromatic substitution and transition-metal-catalyzed coupling reactions. The ester group provides a handle for selective transformations, while the compound exhibits good bench stability and ease of purification—key attributes for scalable synthesis and process development.
Synthesis
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Route1
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In-stock
75308-46-2 -
64-17-5 - ~%
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In-stock
1604-14-4
References
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ACTELION PHARMACEUTICALS LTD Patent: WO2009/24905 A1, 2009 ; Location in patent: Page/Page column 51 ; WO 2009/024905 A1
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Route2
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101990-72-1
- ~%
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In-stock
1604-14-4
References
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Ciba-Geigy Corporation Patent: US4968344 A1, 1990 ;
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Route3
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7664-93-9
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In-stock
5398-44-7 - ~%
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In-stock
1604-14-4
References
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The Wellcome Foundation Limited Patent: US5202356 A1, 1993 ;
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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 39.19
- LogP 2.5651
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 2
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