Methyl 4-bromo-2-nitrobenzoate

Name: Methyl 4-bromo-2-nitrobenzoate
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CAS No. 158580-57-5
Cat. No. CS-W022847
Purity≥98%
MDL No.MFCD10699645

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Methyl 4-bromo-2-nitrobenzoate|CS-W022847

Structure of 158580-57-5

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Description

Methyl 4-bromo-2-nitrobenzoate features a bromine atom at the para position relative to the ester group and a nitro substituent at the ortho position, creating a highly electron-deficient aromatic scaffold. This combination enables selective cross-coupling reactions under palladium catalysis, delivering complex substituted benzoates with high regiocontrol. The molecule exhibits excellent stability under standard bench conditions and integrates seamlessly into synthetic sequences requiring orthogonal functionalization.

Application

Methyl 4-bromo-2-nitrobenzoate serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable bromo group. The nitro functionality provides a handle for selective reduction and subsequent functionalization, while the ester group offers compatibility with standard deprotection and transformation protocols. Its bench-stable nature and predictable reactivity make it well-suited for multi-step synthesis of heterocyclic scaffolds and pharmaceutical intermediates.

General Information

CAS No. 158580-57-5
Cat. No. CS-W022847
Purity ≥98%
MDL No. MFCD10699645
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆BrNO₄
Molecular Weight 260.04
Synonym(s) Benzoic acid, 4-bromo-2-nitro-, methyl ester
SMILES O=C(OC)C1=CC=C(Br)C=C1[N+]([O-])=O

Computational Chemistry Data

TPSA 69.44
LogP 2.1439
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

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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Other Classifications

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 4-bromo-2-nitrobenzoate

CAS No. 158580-57-5

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