Lot numbers can be found on the outside label of a product:
6-Chloro-2-methylquinoline
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CAS No. 92-46-6
- Cat. No. CS-0113039
- Purity≥98%
- MDL No.MFCD00051735
*For research and further manufacturing use only, not for direct human use.
Structure of 92-46-6
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General Information
- CAS No. 92-46-6
- Cat. No. CS-0113039
- Purity ≥98%
- MDL No. MFCD00051735
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₈ClN
- Molecular Weight 177.63
- Synonym(s) 6-Chloroquinaldine
- SMILES CC1=NC2=CC=C(Cl)C=C2C=C1
Description
6-Chloro-2-methylquinoline is a heterocyclic scaffold featuring a chlorine substituent at the 6-position and a methyl group at the 2-position, enabling tailored electronic and steric properties. This configuration enhances solubility in organic media while maintaining stability under standard reaction conditions. The compound serves as a key building block in medicinal chemistry, particularly for developing kinase inhibitors and bioactive small molecules where halogen bonding and lipophilic interactions are advantageous.
Application
6-Chloro-2-methylquinoline serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C6 position via palladium-catalyzed cross-coupling reactions. Its methyl group at C2 enhances electronic modulation and provides steric control, while the chloro substituent offers high reactivity in Suzuki, Stille, and Negishi couplings. The scaffold exhibits excellent bench stability and compatibility with diverse reaction conditions, facilitating efficient access to complex quinoline-based pharmacophores.
Synthesis
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Route1
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1004545-72-5 - ~92%
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In-stock
92-46-6
References
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Zhang, Zuhui; Tan, Jiajing; Wang, Zhiyong Organic Letters, 2008 , vol. 10, # 2 p. 173 - 175
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Route2
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106-47-8
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109-92-2
- ~74%
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In-stock
92-46-6
References
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Verma, Sanny; Verma, Deepak; Jain, Suman L. Tetrahedron Letters, 2014 , vol. 55, # 15 p. 2406 - 2409
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Route3
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106-47-8
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123-73-9
- ~88%
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In-stock
92-46-6
References
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Chaskar, Atul; Padalkar, Vikas; Phatangare, Kiran; Langi, Bhushan; Shah, Chetan Synthetic Communications, 2010 , vol. 40, # 15 p. 2336 - 2340
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS05,GHS07
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Signal Word : Danger
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UN#: 1759
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Class : 8
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Packing Group : Ⅲ
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Hazard Statements : H302-H315-H318-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-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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