Methyl 3-bromo-4-methoxybenzoate

Name: Methyl 3-bromo-4-methoxybenzoate
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CAS No. 35450-37-4
Cat. No. CS-W012726
Purity≥96%
MDL No.MFCD00210463

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Methyl 3-bromo-4-methoxybenzoate|CS-W012726

Structure of 35450-37-4

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General Information

CAS No. 35450-37-4
Cat. No. CS-W012726
Purity ≥96%
MDL No. MFCD00210463
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₉BrO₃
Molecular Weight 245.07
Synonym(s) Methyl 3-Bromo-p-anisate
SMILES O=C(OC)C1=CC=C(OC)C(Br)=C1

Description

Methyl 3-bromo-4-methoxybenzoate features a bromine atom at the meta position relative to the ester, paired with a para-methoxy group that enhances electron density. This combination enables selective functionalization in cross-coupling reactions. The methyl ester facilitates downstream derivatization, while the molecule exhibits stability under standard bench conditions and compatibility with palladium-catalyzed transformations.

Application

Methyl 3-bromo-4-methoxybenzoate serves as a versatile building block for Suzuki-Miyaura and Negishi coupling reactions, enabling efficient construction of biaryl scaffolds. The bromo group exhibits high reactivity under standard palladium catalysis, while the methoxy and ester functionalities provide orthogonal handles for further derivatization. Its bench-stable crystalline form facilitates handling and purification, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

Route1
- 121-98-2
- ~99%
- In-stock
  
  35450-37-4
References
- Ogura, Tetsuhiro; Usuki, Toyonobu Tetrahedron, 2013 , vol. 69, # 13 p. 2807 - 2815
Route2
- In-stock
  
  99-58-1
- 74-88-4
- ~92%
- In-stock
  
  35450-37-4
References
- ELI LILLY AND COMPANY Patent: WO2005/100301 A1, 2005 ; Location in patent: Page/Page column 55 ; WO 2005/100301 A1
Route3
- In-stock
  
  14348-41-5
- 74-88-4
- ~%
- In-stock
  
  35450-37-4
References
- WO2009/78983 A1, ; Page/Page column 86 ; WO 2009/078983 A1

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 35.53
LogP 2.2443
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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Methyl 3-bromo-4-methoxybenzoate

CAS No. 35450-37-4

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