METHYL-2-BROMO-4-BROMOMETHYLBENZOATE

Methyl 2-bromo-4-(bromomethyl)benzoate (CAS 128577-48-0) is a strategically bifunctional halogenated aromatic ester engineered for pharmaceutical intermediate synthesis, agrochemical development, and materials science applications. This molecule integrates a benzoate core—a benzene ring with a methyl ester substituent—with two distinct bromine functionalities: an aryl bromine at the C2 position and a benzyl bromine (bromomethyl) at the C4 position. This dual-bromine architecture with differentiated reactivity enables orthogonal synthetic strategies: the benzyl bromide is highly reactive towards nucleophilic substitution (SN2), while the aryl bromide is suited for Pd-catalyzed cross-coupling (Suzuki, Stille, Negishi). The methyl ester moiety provides additional versatility for hydrolysis to the acid, transesterification, or amide coupling. Compared to its positional isomer (CAS 78471-43-9, 4-bromo-2-bromomethyl), this compound features reversed substitution patterns (2-Br/4-CH₂Br vs. 4-Br/2-CH₂Br), which may influence steric accessibility and reaction kinetics in sequential functionalization. This intermediate is particularly valuable for constructing complex biaryl systems, fused heterocycles, kinase inhibitor cores, and functional materials where controlled sequential derivatization at the bromine sites is critical. Manufactured under controlled conditions, it supports drug discovery programs requiring modular access to differentially halogenated aromatic esters with tunable reactivity. Related Categories: Mol file: 128577-48-0.mol

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Product Name	Methyl 2-bromo-4-(bromomethyl)benzoate
CAS Number	128577-48-0
Chinese Name	2-溴-4-溴甲基苯甲酸甲酯
Synonyms	Methyl 2-bromo-4-(bromomethyl)benzoate; Methyl 4-(bromomethyl)-2-bromobenzoate; 2-Bromo-4-(bromomethyl)benzoic acid methyl ester
Chinese Synonyms	2-溴-4-溴甲基苯甲酸甲酯; 4-溴甲基-2-溴苯甲酸甲酯
Molecular Formula	C₉H₈Br₂O₂
Molecular Weight	307.97 g/mol
Purity	≥ 98% (HPLC/GC area normalization)
Product Category	Pharmaceutical Intermediates / Benzoic Acid Derivatives / Orthogonal Dihalides
Appearance	White to Off-white Crystalline Solid
Melting Point	~55-60°C (estimated, may exist as low-melting solid)
Storage Conditions	Store at 2-8°C under inert atmosphere (nitrogen), protected from light and moisture. Handle with caution: Lachrymator and alkylating agent. Use appropriate PPE (gloves, goggles) and operate in a fume hood. Avoid contact with strong bases and nucleophiles.
Shelf Life	18-24 months under recommended storage conditions
Packaging	100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements (amber glass recommended)
Applications	Kinase inhibitor synthesis, biaryl construction via sequential coupling, heterocyclic library construction, agrochemical intermediate synthesis, functional material precursor, orthogonal functionalization studies
Reactivity	Suitable for nucleophilic substitution (C4-CH₂Br), Pd-catalyzed cross-coupling (C2-ArBr), ester hydrolysis, transesterification, amide coupling (after hydrolysis), and sequential derivatization
Special Note	✅ Orthogonal Dihalo Scaffold—Benzyl Br (C4, SN2) vs. Aryl Br (C2, Cross-coupling). Positional Isomer of CAS 78471-43-9 (reversed Br/CH₂Br positions). Potent Alkylating Agent—handle with appropriate PPE. Part of our halogenated aromatic ester series.