Methyl 2-bromo-3-fluorobenzoate

Name: Methyl 2-bromo-3-fluorobenzoate
Brand: ChemScene
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CAS No. 647020-71-1
Cat. No. CS-0096404
Purity≥97%
MDL No.None

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Methyl 2-bromo-3-fluorobenzoate|CS-0096404

Structure of 647020-71-1

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General Information

CAS No. 647020-71-1
Cat. No. CS-0096404
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆BrFO₂
Molecular Weight 233.03
Synonym(s) Benzoic acid, 2-bromo-3-fluoro-, methyl ester
SMILES O=C(OC)C1=CC=CC(F)=C1Br

Description

Methyl 2-bromo-3-fluorobenzoate features a strategically positioned bromo and fluoro substituent on the aromatic ring, enabling selective coupling reactions in synthetic chemistry. The ester functionality supports further derivatization, while the halogen pattern enhances reactivity in palladium-catalyzed transformations. This compound serves as a key intermediate for bioactive molecule synthesis.

Application

Methyl 2-bromo-3-fluorobenzoate serves as a versatile building block in medicinal chemistry and synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The bromine center facilitates efficient Suzuki, Stille, or Negishi coupling, while the fluorine substituent enhances metabolic stability and modulates electronic properties. Its bench-stable nature and straightforward purification support scalable synthesis of complex heterocyclic scaffolds and bioactive molecules.

Synthesis

Route1
- 67-56-1
- In-stock
  
  132715-69-6
- ~%
- In-stock
  
  647020-71-1
References
- NEWLINK GENETICKS CORPORATION; MAUTINO, Mario; KUMAR, Sanjeev; WALDO, Jesse; JAIPURI, Firoz; KESHARWANI, Tanay Patent: WO2012/142237 A1, 2012 ; Location in patent: Page/Page column 101 ; WO 2012/142237 A1
Route2
- 186581-53-3
- In-stock
  
  132715-69-6
- ~90%
- In-stock
  
  647020-71-1
References
- Heiss, Christophe; Rausis, Thierry; Schlosser, Manfred Synthesis, 2005 , # 4 art. no. T11504SS, p. 617 - 621
Route3
- In-stock
  
  1121-86-4
- ~%
- In-stock
  
  647020-71-1
References
- Heiss, Christophe; Rausis, Thierry; Schlosser, Manfred Synthesis, 2005 , # 4 art. no. T11504SS, p. 617 - 621

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-3-fluorobenzoate

CAS No. 647020-71-1

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