Methyl 2-amino-5-bromo-3-iodobenzoate

Name: Methyl 2-amino-5-bromo-3-iodobenzoate
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CAS No. 289039-83-4
Cat. No. CS-0105628
Purity≥95%
MDL No.MFCD00673015

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Methyl 2-amino-5-bromo-3-iodobenzoate|CS-0105628

Structure of 289039-83-4

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General Information

CAS No. 289039-83-4
Cat. No. CS-0105628
Purity ≥95%
MDL No. MFCD00673015
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₇BrINO₂
Molecular Weight 355.96
Synonym(s) Benzoic acid, 2-amino-5-bromo-3-iodo-, methyl ester
SMILES O=C(OC)C1=CC(Br)=CC(I)=C1N

Description

Methyl 2-amino-5-bromo-3-iodobenzoate features a uniquely substituted aromatic core bearing bromo and iodo groups at meta positions relative to the ester, with an amino group ortho to the ester. This electron-deficient scaffold enables direct functionalization in cross-coupling reactions, integrating seamlessly into complex molecular architectures under standard conditions.

Application

Methyl 2-amino-5-bromo-3-iodobenzoate serves as a versatile building block for palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl scaffolds. The strategically positioned amino, bromo, and iodo groups offer orthogonal reactivity for sequential functionalization, while the methyl ester provides a handle for downstream derivatization. Bench-stable and compatible with standard synthetic protocols, it facilitates rapid access to complex substituted aromatic systems relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  52727-57-8
- ~83%
- In-stock
  
  289039-83-4
References
- Conte-Mayweg, Aurelia; Kuehne, Holger; Luebbers, Thomas; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe Patent: US2006/30613 A1, 2006 ; Location in patent: Page/Page column 21-22 ;

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 52.32
LogP 2.4225
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Iodide

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Methyl 2-amino-5-bromo-3-iodobenzoate

CAS No. 289039-83-4

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