2-Bromo-4-chloro-6-methoxyaniline

Name: 2-Bromo-4-chloro-6-methoxyaniline
Brand: ChemScene
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CAS No. 1261895-84-4
Cat. No. CS-0150463
Purity≥98%
MDL No.MFCD18311825

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2-Bromo-4-chloro-6-methoxyaniline|CS-0150463

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General Information

CAS No. 1261895-84-4
Cat. No. CS-0150463
Purity ≥98%
MDL No. MFCD18311825
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₇BrClNO
Molecular Weight 236.49
Synonym(s) None
SMILES COC1=CC(=CC(=C1N)Br)Cl

Description

2-Bromo-4-chloro-6-methoxyaniline features a tri-substituted aniline core with complementary halogen and methoxy functionalities, enabling direct coupling in cross-coupling reactions. The electron-donating methoxy group enhances nucleophilicity at the ortho position, while the bromo and chloro substituents provide orthogonal reactivity for sequential functionalization. This compound serves as a high-precision intermediate in the synthesis of complex heterocycles and bioactive molecules.

Application

2-Bromo-4-chloro-6-methoxyaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted heterocycles via Pd-catalyzed cross-coupling reactions. Its ortho-bromo functionality facilitates C–C bond formation under standard Suzuki, Stille, or Negishi conditions, while the meta-chloro and para-methoxy groups provide orthogonal reactivity and enhanced solubility. The compound exhibits excellent bench stability and is readily purified by crystallization, supporting reliable scale-up in process development workflows.

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-P362

Quality Control

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Computational Chemistry Data

TPSA 35.25
LogP 2.6933
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Bromo-4-chloro-6-methoxyaniline

CAS No. 1261895-84-4

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