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2-Bromo-6-methylpyridine-3-carbonitrile
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CAS No. 155265-57-9
- Cat. No. CS-0051989
- Purity≥96%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 155265-57-9
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General Information
- CAS No. 155265-57-9
- Cat. No. CS-0051989
- Purity ≥96%
- MDL No. None
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₇H₅BrN₂
- Molecular Weight 197.03
- Synonym(s) 2-Bromo-6-methylnicotinonitrile
- SMILES CC1=CC=C(C#N)C(Br)=N1
Description
2-Bromo-6-methylpyridine-3-carbonitrile features a strategically positioned bromine atom and electron-withdrawing nitrile group on a methyl-substituted pyridine scaffold, enabling direct functionalization in cross-coupling and nucleophilic substitution reactions. The sterically accessible C2 position facilitates efficient derivatization under standard conditions, while the bench-stable, moisture-tolerant nature ensures reliable handling in synthetic workflows.
Application
2-Bromo-6-methylpyridine-3-carbonitrile serves as a versatile building block in medicinal chemistry and heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its bromo and cyano functional groups. The methyl substituent enhances electron density at the pyridine ring, improving reactivity in C–H functionalization and Suzuki-Miyaura coupling protocols. Bench-stable and compatible with standard purification methods, it facilitates efficient construction of complex pyridine-based scaffolds used in pharmaceutical development.
Synthesis
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Route1
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In-stock
4241-27-4 - ~71%
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In-stock
155265-57-9
References
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Banyu Pharmaceutical Co., Ltd. Patent: US6114524 A1, 2000 ;
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Route2
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In-stock
72918-03-7 - ~77%
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In-stock
155265-57-9
References
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Victory, P.; Borrell, J. I.; Castejon, P.; Martinez-Teipel, B.; Vidal-Ferran, A. Anales de Quimica, 1993 , vol. 89, p. 625 - 628
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Route3
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1163297-78-6 - ~%
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In-stock
155265-57-9
References
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Maloney, Kevin M.; Nwakpuda, Emily; Kuethe, Jeffrey T.; Yin, Jingjun Journal of Organic Chemistry, 2009 , vol. 74, # 14 p. 5111 - 5114
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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-H312-H315-H319-H332-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 36.68
- LogP 2.0242
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 0
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Key Words
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