Lot numbers can be found on the outside label of a product:
6-Nitro-1,2,3,4-tetrahydroquinoline
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CAS No. 14026-45-0
- Cat. No. CS-0043686
- Purity≥96%
- MDL No.MFCD00541472
*For research and further manufacturing use only, not for direct human use.
Structure of 14026-45-0
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General Information
- CAS No. 14026-45-0
- Cat. No. CS-0043686
- Purity ≥96%
- MDL No. MFCD00541472
- Storage RT, protect from light
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₉H₁₀N₂O₂
- Molecular Weight 178.19
- Synonym(s) 6-Nitro-1,2,3,4-tetrahydro-chinolin
- SMILES O=[N+]([O-])C1=CC2=C(C=C1)NCCC2
Description
6-Nitro-1,2,3,4-tetrahydroquinoline features a fused heterocyclic core with a nitro group at the 6-position, imparting strong electron-withdrawing character. This configuration enhances reactivity in transition-metal-catalyzed couplings and facilitates downstream functionalization. The saturated quinoline framework ensures improved solubility and stability compared to aromatic analogs, enabling reliable use in synthetic sequences requiring moisture-tolerant, bench-stable intermediates.
Application
6-Nitro-1,2,3,4-tetrahydroquinoline serves as a versatile intermediate in medicinal chemistry, enabling direct functionalization at the aromatic ring and facilitating subsequent reduction or coupling reactions. Its nitro group provides strong electron-withdrawing character, enhancing regioselectivity in electrophilic substitution and supporting efficient transition-metal-catalyzed cross-couplings. The tetrahydroquinoline core offers metabolic stability and favorable pharmacokinetic properties, making it a practical scaffold for building diverse heterocyclic libraries. Bench-stable and readily purified by column chromatography, it functions reliably in multi-step synthesis workflows.
Synthesis
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Route1
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In-stock
22246-16-8 - ~%
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In-stock
14026-45-0
References
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WO2013/159095 A1, ; Paragraph 0083 ;
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Route2
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1290608-22-8 - ~82%
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In-stock
14026-45-0
References
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Cordeiro, Alessandra; Shaw, Julian; O'Brien, John; Blanco, Fernando; Rozas, Isabel European Journal of Organic Chemistry, 2011 , # 8 p. 1504 - 1513
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Route3
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924829-59-4
- ~90%
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In-stock
14026-45-0
References
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Cordeiro, Alessandra; Shaw, Julian; O'Brien, John; Blanco, Fernando; Rozas, Isabel European Journal of Organic Chemistry, 2011 , # 8 p. 1504 - 1513
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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 55.17
- LogP 1.9529
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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