Methyl 4-bromo-2-chlorobenzoate

Name: Methyl 4-bromo-2-chlorobenzoate
Brand: ChemScene
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CAS No. 185312-82-7
Cat. No. CS-W003730
Purity≥97%
MDL No.MFCD10566823

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Methyl 4-bromo-2-chlorobenzoate|CS-W003730

Structure of 185312-82-7

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General Information

CAS No. 185312-82-7
Cat. No. CS-W003730
Purity ≥97%
MDL No. MFCD10566823
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆BrClO₂
Molecular Weight None
Synonym(s) 4-Bromo-2-Chloro-Benzoic Acid Methyl Ester
SMILES COC(C1=C(Cl)C=C(Br)C=C1)=O

Description

Methyl 4-bromo-2-chlorobenzoate features a dual halogenated aromatic core with bromine at the para position and chlorine at the ortho position relative to the ester group. This electron-deficient scaffold enables direct functionalization in cross-coupling reactions, serving as a key building block for pharmaceutical intermediates and agrochemicals under standard conditions.

Application

Methyl 4-bromo-2-chlorobenzoate serves as a versatile building block in cross-coupling chemistry, enabling palladium-catalyzed Suzuki, Stille, and Negishi reactions due to its orthogonal halogen reactivity. The ortho-chloro and para-bromo substituents provide distinct sites for selective functionalization, while the methyl ester group supports downstream transformations including hydrolysis and amidation. Bench-stable and readily purified by recrystallization, it is well-suited for medicinal chemistry campaigns and process-scale synthesis.

Synthesis

Route1
- In-stock
  
  59748-90-2
- ~95%
- In-stock
  
  185312-82-7
References
- Eli Lilly and Company Patent: US5786325 A1, 1998 ;
Route2
- 67-56-1
- In-stock
  
  59748-90-2
- ~97%
- In-stock
  
  185312-82-7
References
- ANACOR PHARMACEUTICALS, INC.; CHEN, Daitao; ORR, Matthew; SLIGAR, Jessica; JACOBS, Robert; PLATTNER, Jacob, J. Patent: WO2011/19618 A1, 2011 ; Location in patent: Page/Page column 149-150 ;
Route3
- In-stock
  
  59748-90-2
- 74-88-4
- ~%
- In-stock
  
  185312-82-7
References
- EP2017257 A1, ; Page/Page column 20 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362+P364

Quality Control

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Computational Chemistry Data

TPSA 26.3
LogP 2.8891
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 4-bromo-2-chlorobenzoate

CAS No. 185312-82-7

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