2-Bromo-5-Methoxyaniline

Name: 2-Bromo-5-Methoxyaniline
Brand: ChemScene
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CAS No. 59557-92-5
Cat. No. CS-W018520
Purity≥97%
MDL No.MFCD00070741

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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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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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General Information

CAS No. 59557-92-5
Cat. No. CS-W018520
Purity ≥97%
MDL No. MFCD00070741
Storage RT, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₈BrNO
Molecular Weight 202.05
Synonym(s) benzenamine, 2-bromo-5-methoxy-
SMILES NC1=CC(OC)=CC=C1Br

Description

2-Bromo-5-methoxyaniline features a bromine substituent at the ortho position relative to the amino group and a methoxy group at the para position, creating a uniquely activated aryl amine. This electronic profile enables direct coupling in Pd-catalyzed cross-coupling reactions without requiring additional protection. The molecule exhibits enhanced solubility in common organic solvents and maintains stability under standard bench conditions, facilitating its use in synthetic workflows targeting functionalized heterocycles and bioactive intermediates.

Application

2-Bromo-5-methoxyaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted anilines via Pd-catalyzed cross-coupling reactions. Its bromine and methoxy functionalities offer orthogonal reactivity for sequential functionalization, while the amine group facilitates direct derivatization or protection. The compound exhibits good bench stability and is compatible with standard purification protocols, making it well-suited for scalable synthesis and high-throughput screening campaigns.

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

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Computational Chemistry Data

TPSA 35.25
LogP 2.0399
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Bromo-5-Methoxyaniline

CAS No. 59557-92-5

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