Lot numbers can be found on the outside label of a product:
2-Chloro-8-methylquinoline
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CAS No. 4225-85-8
- Cat. No. CS-W021670
- Purity≥98%
- MDL No.MFCD11108682
*For research and further manufacturing use only, not for direct human use.
Structure of 4225-85-8
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General Information
- CAS No. 4225-85-8
- Cat. No. CS-W021670
- Purity ≥98%
- MDL No. MFCD11108682
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₈ClN
- Molecular Weight 177.63
- Synonym(s) Quinoline, 2-chloro-8-methyl-
- SMILES CC1=C2N=C(Cl)C=CC2=CC=C1
Description
2-Chloro-8-methylquinoline is a heterocyclic compound featuring a quinoline core with strategically positioned chlorine and methyl substituents. This electron-deficient scaffold integrates readily into transition metal-catalyzed coupling reactions, serving as a robust ligand in palladium-mediated transformations. The steric profile and electronic tuning offered by the 2-chloro and 8-methyl groups enhance coordination stability and reactivity control in catalytic systems.
Application
2-Chloro-8-methylquinoline serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its reactive C–Cl bond and electron-deficient quinoline core. The 8-methyl group enhances regioselectivity in subsequent functionalizations, while the molecule exhibits bench stability and ease of purification. It functions as a key scaffold for constructing bioactive heterocycles and pharmaceutical intermediates.
Synthesis
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Route1
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4053-38-7 - ~82%
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In-stock
4225-85-8
References
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ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E. Patent: WO2010/75200 A1, 2010 ; Location in patent: Page/Page column 90-91 ; WO 2010/075200 A1
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Route2
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In-stock
4053-36-5 - ~61%
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In-stock
4225-85-8
References
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AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge Patent: WO2011/143365 A1, 2011 ; Location in patent: Page/Page column 183 ; WO 2011/143365 A1
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Route3
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95-53-4
- ~%
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In-stock
4225-85-8
References
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AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge Patent: WO2011/143365 A1, 2011 ; WO 2011/143365 A1
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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 12.89
- LogP 3.19662
- H_Acceptors 1
- H_Donors 0
- Rotatable_Bonds 0
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Key Words
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