Lot numbers can be found on the outside label of a product:
4-Iodopyridin-2-amine
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CAS No. 552331-00-7
- Cat. No. CS-0040803
- Purity≥97%
- MDL No.MFCD09038163
*For research and further manufacturing use only, not for direct human use.
Structure of 552331-00-7
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General Information
- CAS No. 552331-00-7
- Cat. No. CS-0040803
- Purity ≥97%
- MDL No. MFCD09038163
- Storage 4°C, protect from light, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₅H₅IN₂
- Molecular Weight 220.01
- Synonym(s) 4-lodopyridin-2-aMine
- SMILES NC1=NC=CC(I)=C1
Description
4-Iodopyridin-2-amine serves as a key building block in the synthesis of functionalized heterocycles, particularly in palladium-catalyzed cross-coupling reactions. The iodine atom enables efficient C–X bond activation, while the pyridin-2-amine moiety provides a directing group for regioselective transformations. This compound exhibits robust stability under standard conditions and facilitates the rapid assembly of complex molecular architectures in medicinal chemistry and materials science applications.
Application
4-Iodopyridin-2-amine serves as a versatile building block in cross-coupling chemistry, enabling efficient access to substituted pyridines via palladium-catalyzed reactions. The iodide group provides high reactivity in Suzuki, Stille, and Negishi couplings, while the ortho-amine functions as a directing group or handles as a hydrogen-bond donor in downstream transformations. Bench-stable and readily purified by chromatography, it facilitates rapid scaffold diversification in medicinal chemistry and materials science applications.
Synthesis
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Route1
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In-stock
22282-70-8 - ~61%
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In-stock
552331-00-7
References
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Takeda Pharmaceutical Company Limited Patent: US2011/39893 A1, 2011 ; Location in patent: Page/Page column 25 ;
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Route2
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504-29-0 - ~62%
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In-stock
552331-00-7
References
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AKAAL PHARMA PTY LTD; GROBELNY, Damian W; GILL, Gurmit S Patent: WO2014/63199 A1, 2014 ; Location in patent: Page/Page column 58; 59 ;
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Route3
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405939-28-8 - ~98%
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In-stock
552331-00-7
References
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Edmondson, Scott D.; Mastracchio, Anthony; Mathvink, Robert J.; He, Jiafang; Harper, Bart; Park, You-Jung; Beconi, Maria; Di Salvo, Jerry; Eiermann, George J.; He, Huaibing; Leiting, Barbara; Leone, Joseph F.; Levorse, Dorothy A.; Lyons, Kathryn; Patel, Reshma A.; Patel, Sangita B.; Petrov, Aleksandr; Scapin, Giovanna; Shang, Jackie; Roy, Ranabir Sinha; Smith, Aaron; Wu, Joseph K.; Xu, Shiyao; Zhu, Bing; Thornberry, Nancy A.; Weber, Ann E. Journal of Medicinal Chemistry, 2006 , vol. 49, # 12 p. 3614 - 3627
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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 38.91
- LogP 1.2684
- H_Acceptors 2
- H_Donors 1
- Rotatable_Bonds 0
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Key Words
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