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2-Chloro-3-nitro-6-phenylpyridine
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CAS No. 187242-88-2
- Cat. No. CS-0186600
- Purity≥97%
- MDL No.MFCD22380358
*For research and further manufacturing use only, not for direct human use.
Structure of 187242-88-2
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General Information
- CAS No. 187242-88-2
- Cat. No. CS-0186600
- Purity ≥97%
- MDL No. MFCD22380358
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₁H₇ClN₂O₂
- Molecular Weight None
- Synonym(s) 2-chloro-3-nitro-6-phenyl pyridine
- SMILES C1=CC=C(C=C1)C2=NC(=C(C=C2)[N+](=O)[O-])Cl
Description
2-Chloro-3-nitro-6-phenylpyridine features a fused pyridine core bearing a chloro group at the 2-position, a nitro substituent at the 3-position, and a phenyl ring attached at the 6-position. This electron-deficient heterocycle serves as a key intermediate in the synthesis of functionalized pharmaceuticals and agrochemicals, offering enhanced reactivity in cross-coupling and nucleophilic substitution processes under standard conditions.
Application
2-Chloro-3-nitro-6-phenylpyridine serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its reactive chloropyridine functionality. The ortho-nitro group enhances electrophilicity and facilitates subsequent reduction or substitution cascades. Its phenyl substituent provides steric and electronic modulation, while the molecule exhibits sufficient bench stability for routine handling. This compound functions effectively in constructing complex pharmaceutical scaffolds and functionalized aryl systems under standard reaction conditions.
Synthesis
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References
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Smithkline Beecham Corporation Patent: US2008/242685 A1, 2008 ; Location in patent: Page/Page column 16 ;
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Route2
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In-stock
102266-15-9 - ~45%
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In-stock
187242-88-2
References
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Troschuetz, Reinhard; Karger, Alexander Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 4 p. 1147 - 1151
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Route3
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In-stock
1131-80-2 - ~%
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In-stock
187242-88-2
References
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Troschutz; Karger Journal of Heterocyclic Chemistry, 1996 , vol. 33, # 6 p. 1815 - 1821
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Safety Information
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GHS Pictogram :
N/A
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GHS No : N/A
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Signal Word : N/A
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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 : N/A
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Precautionary Statements : N/A
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Quality Control
Computational Chemistry Data
- TPSA 56.03
- LogP 3.3102
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 2
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Key Words
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