Lot numbers can be found on the outside label of a product:
methyl 4-cyano-3-fluorobenzoate
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CAS No. 268734-34-5
- Cat. No. CS-W000768
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 268734-34-5
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General Information
- CAS No. 268734-34-5
- Cat. No. CS-W000768
- Purity ≥97%
- MDL No. None
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₉H₆FNO₂
- Molecular Weight 179.15
- Synonym(s) benzoic acid, 4-cyano-3-fluoro-, methyl ester
- SMILES COC(=O)c1ccc(C#N)c(F)c1
Description
Methyl 4-cyano-3-fluorobenzoate features a strategically positioned cyano and fluorine substituent on the aromatic ring, delivering enhanced electron-withdrawing character and improved metabolic stability. This combination enables efficient coupling in transition-metal-catalyzed reactions, particularly in Suzuki-Miyaura and Buchwald-Hartwig transformations, where the fluorine acts as a traceless directing group. The ester functionality provides solubility in common organic solvents and facilitates downstream derivatization.
Application
Methyl 4-cyano-3-fluorobenzoate serves as a versatile building block in medicinal chemistry, enabling efficient access to fluorinated heterocycles and bioactive scaffolds. Its orthogonal functionality—cyano, fluoro, and ester groups—permits selective transformations under standard conditions. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for multi-step synthesis campaigns and process development.
Synthesis
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Route1
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67-56-1 -
201230-82-2
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In-stock
105942-08-3 - ~98%
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In-stock
268734-34-5
References
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Martinelli, Joseph R.; Watson, Donald A.; Freckmann, Dominique M. M.; Barder, Timothy E.; Buchwald, Stephen L. Journal of Organic Chemistry, 2008 , vol. 73, # 18 p. 7102 - 7107
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Route2
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67-56-1
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In-stock
176508-81-9 - ~88%
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In-stock
268734-34-5
References
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MERCK SERONO S.A. Patent: WO2009/80663 A1, 2009 ; Location in patent: Page/Page column 96-97 ; WO 2009/080663 A1
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Route3
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In-stock
105942-08-3
- ~%
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In-stock
268734-34-5
References
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Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo Patent: US2002/115640 A1, 2002 ; Title/Abstract Full Text Show Details Claiborne, Akiyo K.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo Patent: US2003/87940 A1, 2003 ;
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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 50.09
- LogP 1.48398
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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