Ethyl 4-bromo-2-methylbenzoate

Ethyl 4-bromo-2-methylbenzoate (CAS 220389-34-4) is a strategically functionalized halogenated aromatic ester engineered for pharmaceutical intermediate synthesis, agrochemical development, and materials science applications. This molecule integrates a benzoate core—a benzene ring with an ethyl ester substituent—with a bromine atom at the C4 position and a methyl group at the C2 position. The ethyl ester moiety serves as a versatile handle for hydrolysis to the free acid, transesterification, or amide coupling (after hydrolysis), while the C4-bromo substituent enables Pd-catalyzed cross-coupling (Suzuki, Stille, Negishi, Sonogashira). The ortho-methyl group provides steric modulation, metabolic stability enhancement, and electronic tuning compared to unsubstituted analogs. Compared to its free acid analog (CAS 68837-59-2), this ethyl ester form offers enhanced lipophilicity and improved membrane permeability for cellular assays. Compared to its tert-butyl ester analog (CAS 445003-37-2), the ethyl group requires base-mediated hydrolysis rather than acid-mediated deprotection, providing orthogonal synthetic flexibility. This intermediate is particularly valuable for constructing NSAID analogs, kinase inhibitor cores, agrochemical actives, and functional materials where controlled ester hydrolysis and cross-coupling diversification are critical. Manufactured under controlled conditions, it supports drug discovery programs requiring modular access to differentially protected halogenated aromatic acids.

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Product Name	Ethyl 4-bromo-2-methylbenzoate
CAS Number	220389-34-4
Chinese Name	4-溴-2-甲基苯甲酸乙酯
Synonyms	Ethyl 4-bromo-2-methylbenzoate; 4-Bromo-2-methylbenzoic acid ethyl ester; Ethyl 2-methyl-4-bromobenzoate
Chinese Synonyms	4-溴-2-甲基苯甲酸乙酯; 2-甲基-4-溴苯甲酸乙酯; 4-溴邻甲苯甲酸乙酯
Molecular Formula	C₁₀H₁₁BrO₂
Molecular Weight	243.09 g/mol
Purity	≥ 98% (HPLC/GC area normalization)
Product Category	Pharmaceutical Intermediates / Benzoic Acid Derivatives / Halogenated Aromatic Esters
Appearance	Colorless to Pale Yellow Liquid
Boiling Point	~260-270°C at 760 mmHg (estimated)
Density	~1.45 g/cm³ at 20°C (estimated)
Refractive Index	n₂₀/D ~1.55 (estimated)
Storage Conditions	Store in a cool, dry, well-ventilated area away from light and moisture. Keep container tightly closed under inert atmosphere (nitrogen). Protect from strong bases to avoid ester hydrolysis and from strong oxidizing agents.
Shelf Life	24 months under recommended storage conditions
Packaging	100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements
Applications	NSAID analog synthesis, kinase inhibitor development, Pd-catalyzed cross-coupling (C4-Br), ester hydrolysis to free acid, agrochemical intermediate synthesis, functional material precursor
Reactivity	Suitable for Pd-catalyzed cross-coupling (C4-Br displacement), ester hydrolysis (NaOH/KOH), transesterification, amide coupling (after hydrolysis), electrophilic aromatic substitution at C3/C5/C6, and sequential functionalization
Special Note	✅ Ethyl Ester Protected Acid—base-labile hydrolysis vs. acid-labile tert-butyl ester (CAS 445003-37-2). C4-Br enables cross-coupling. Distinct from free acid (CAS 68837-59-2) by protection status. Part of our halogenated aromatic ester series.