Lot numbers can be found on the outside label of a product:
4-Chloro-3-nitro-2(1H)-pyridinone
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CAS No. 165547-79-5
- Cat. No. CS-0020074
- Purity≥98%
- MDL No.MFCD09701353
*For research and further manufacturing use only, not for direct human use.
Structure of 165547-79-5
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General Information
- CAS No. 165547-79-5
- Cat. No. CS-0020074
- Purity ≥98%
- MDL No. MFCD09701353
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₅H₃ClN₂O₃
- Molecular Weight 174.54
- Synonym(s) 4-Chloro-3-nitro-1,2-dihydropyridin-2-one; 4-Chloro-3-nitro-2-hydroxypyridine; 4-Chloro-3-nitro-2-pyridone; 4-Chloro-3-nitropyridin-2-ol; 4-chloro-3-nitropyridin-2(1H)-one
- SMILES O=C1C([N+]([O-])=O)=C(Cl)C=CN1
Description
4-Chloro-3-nitro-2(1H)-pyridinone features a fused heterocyclic core with orthogonal electron-withdrawing groups: a chloro substituent at C4 and a nitro group at C3. This combination imparts high electrophilicity, enabling direct coupling in transition-metal-catalyzed cross-coupling reactions. The pyridinone scaffold ensures stability under standard reaction conditions while offering tunable reactivity for synthetic applications in medicinal chemistry and agrochemical development.
Application
4-Chloro-3-nitro-2(1H)-pyridinone serves as a versatile building block in heterocyclic synthesis, enabling efficient construction of pyridine-based scaffolds through nucleophilic substitution and coupling reactions. The chloro group at C4 facilitates reliable functionalization under mild conditions, while the nitro substituent enhances electrophilicity for downstream transformations. Its bench-stable crystalline form simplifies handling and purification, making it well-suited for medicinal chemistry campaigns and process development workflows.
Synthesis
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Route1
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In-stock
89282-12-2 - ~89%
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In-stock
165547-79-5
References
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Cleator, Ed; Scott, Jeremy P.; Avalle, Paulo; Bio, Matthew M.; Brewer, Sarah E.; Davies, Antony J.; Gibb, Andrew D.; Sheen, Faye J.; Stewart, Gavin W.; Wallace, Debra J.; Wilson., Robert D. Organic Process Research and Development, 2013 , vol. 17, # 12 p. 1561 - 1567
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Route2
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In-stock
5975-12-2 - ~46%
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In-stock
165547-79-5
References
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Ahn, Sung Oh; Park, Chan Hee; Im, Jun Hwan; Lee, Soon Ok; Lee, Kyoung June; Cho, Seong Wook; Ko, Kwang Seok; Han, Sun Young; Lee, Won Il Patent: US2011/28467 A1, 2011 ; Location in patent: Page/Page column 53 ; US 20110028467 A1
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Route3
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In-stock
6980-08-1 - ~%
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In-stock
165547-79-5
References
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WO2010/89773 A2, ; Page/Page column 15 ;
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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 76
- LogP 0.9365
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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