Lot numbers can be found on the outside label of a product:
5-Chloro-2-hydroxy-3-nitropyridine
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CAS No. 21427-61-2
- Cat. No. CS-W002380
- Purity≥98%
- MDL No.MFCD00114884
*For research and further manufacturing use only, not for direct human use.
Structure of 21427-61-2
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General Information
- CAS No. 21427-61-2
- Cat. No. CS-W002380
- Purity ≥98%
- MDL No. MFCD00114884
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₅H₃ClN₂O₃
- Molecular Weight 174.54
- Synonym(s) 5-chloro-3-nitropyridin-2(1H)-one; 5-Chloro-2-hydroxy-3-nitropyridine
- SMILES O=C1C([N+]([O-])=O)=CC(Cl)=CN1
Description
5-Chloro-2-hydroxy-3-nitropyridine features a trifunctional pyridine core integrating a chlorine atom, a hydroxyl group, and a nitro moiety. This electron-deficient heterocycle enables selective coupling reactions under mild conditions. The hydroxyl group enhances solubility in polar solvents while the nitro group serves as a potent acceptor for nucleophilic substitution. Bench-stable and moisture-tolerant, this compound functions as a key intermediate in the synthesis of pharmaceuticals and agrochemicals.
Application
5-Chloro-2-hydroxy-3-nitropyridine serves as a versatile building block in heterocyclic synthesis, enabling efficient functionalization at the C-2 and C-3 positions. The ortho-nitro and hydroxyl groups facilitate electrophilic substitution and metal-catalyzed coupling reactions, while the 5-chloro substituent provides a handle for palladium-mediated cross-coupling. Its bench-stable nature and compatibility with standard purification methods make it suitable for iterative synthetic sequences in medicinal chemistry and agrochemical development.
Synthesis
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Route1
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In-stock
1072-98-6 - ~81%
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In-stock
21427-61-2
References
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Ciba-Geigy Corporation Patent: US5274100 A1, 1993 ;
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Route2
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In-stock
4214-79-3 - ~%
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In-stock
21427-61-2
References
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Bioorganic and Medicinal Chemistry Letters, , vol. 23, # 13 p. 3983 - 3987
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Route3
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5409-39-2 - ~%
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In-stock
21427-61-2
References
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Journal of the American Pharmaceutical Association (1912-1977), , vol. 38, p. 70 Journal of the Chemical Society, , p. 2590,2593
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS05,GHS07
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Signal Word : Danger
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UN#: 1759
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Class : 8
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Packing Group : Ⅲ
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Hazard Statements : H302-H315-H318-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 76
- LogP 0.9365
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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