Methyl 2-bromo-4-fluorobenzoate

Name: Methyl 2-bromo-4-fluorobenzoate
Brand: ChemScene
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CAS No. 653-92-9
Cat. No. CS-0041783
Purity≥98%
MDL No.MFCD06204026

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FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Methyl 2-bromo-4-fluorobenzoate|CS-0041783

Structure of 653-92-9

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General Information

CAS No. 653-92-9
Cat. No. CS-0041783
Purity ≥98%
MDL No. MFCD06204026
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆BrFO₂
Molecular Weight 233.03
Synonym(s) Methyl 4-fluoro-2-bromobenzoate
SMILES COC(=O)C1=C(Br)C=C(F)C=C1

Description

Methyl 2-bromo-4-fluorobenzoate features a strategically positioned bromine and fluorine substituent on the aromatic ring, enabling selective cross-coupling reactions. The ester functionality provides stability and facilitates downstream derivatization under standard conditions. This ortho-bromo, para-fluoro motif supports efficient palladium-catalyzed transformations in complex molecule synthesis.

Application

Methyl 2-bromo-4-fluorobenzoate serves as a versatile building block in medicinal chemistry and synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its ortho-bromo and para-fluoro substituents. The methyl ester group provides a handle for further functionalization, while the molecule exhibits excellent bench stability and compatibility with standard reaction conditions, facilitating efficient synthesis of complex aryl scaffolds.

Synthesis

Route1
- 67-56-1
- In-stock
  
  1006-41-3
- ~94%
- In-stock
  
  653-92-9
References
- Kawai, Junya; Chikkade, Prasanna Kumara; Shimizu, Yohei; Kanai, Motomu Angewandte Chemie - International Edition, 2013 , vol. 52, # 28 p. 7177 - 7180
Route2
- In-stock
  
  1006-41-3
- 18107-18-1
- ~99%
- In-stock
  
  653-92-9
References
- Allison, Brett D.; Gomez, Laurent; Grice, Cheryl A.; Hack, Michael D.; Morrow, Brian J.; Motley, S. Timothy; Santillan, Alejandro; Shaw, Karen J.; Schwarz, Kimberly L.; Tang, Liu Y.; Venkatesan, Hariharan; Wiener, John J. M. Patent: US2006/223810 A1, 2006 ; Location in patent: Page/Page column 28 ;
Route3
- In-stock
  
  1006-41-3
- 74-88-4
- ~%
- In-stock
  
  653-92-9
References
- US6407250 B1, ; US6511999 B2, ; US2002/128233 A1, ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 26.3
LogP 2.3748
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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Methyl 2-bromo-4-fluorobenzoate

CAS No. 653-92-9

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