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2‑Bromo‑2′‑methoxyacetophenone (IUPAC name: 2‑bromo‑1‑(2‑methoxyphenyl)ethanone, also known as o‑methoxyphenacyl bromide, 2‑methoxyphenacyl bromide, α‑bromo‑2′‑methoxyacetophenone, bromomethyl 2‑methoxyphenyl ketone, CAS: 31949‑21‑0) is a highly reactive bromoacetyl aromatic ketone bearing a methoxy group at the ortho position of the phenyl ring. Its molecular formula is C₉H₉BrO₂, with a molecular weight of 229.07 g/mol, and it appears as a white to off‑white or greyish‑green crystalline solid with a melting point of 43‑45°C.

The ortho‑methoxy substitution is the key to the compound’s unique synthetic value: the bromoacetyl group can undergo nucleophilic substitution with nitrogen, oxygen and sulfur nucleophiles, while the ortho‑methoxy directing group imposes strict regiocontrol in heterocyclic cyclisations — a feature that is absent in 4′‑methoxy or unsubstituted regioisomers, which fail to replicate either the MurA binding or the correct heterocyclic regiochemistry required for biologically active scaffolds. This robust, well‑characterised halogenated ketone is an essential building block for medicinal chemistry, pharmaceutical development, agrochemical research and material science.

From a synthetic perspective, 2‑bromo‑2′‑methoxyacetophenone can be prepared by α‑bromination of 2′‑methoxyacetophenone. In one high‑yielding protocol, copper(II) bromide (2.97 g, 6.66 mmol) is combined with 1‑(2‑methoxyphenyl)ethanone (0.50 g, 3.33 mmol) in ethyl acetate and chloroform, and the mixture is stirred at 70 °C under a nitrogen atmosphere for 8 hours. The crude product is purified by column chromatography to afford the desired compound in 96 % yield as a brown liquid.

The global antibacterial drug market, valued at approximately USD 44 billion in 2024, is projected to grow at a compound annual growth rate (CAGR) of 4‑5 % through 2032, driven by the increasing prevalence of drug‑resistant bacterial infections and the urgent need for new classes of antibiotics that act via novel mechanisms of action.

Core Application Fields

Market demand for 2‑bromo‑2′‑methoxyacetophenone is strongly concentrated in four high‑value sectors: antibacterial research (≈35‑40 % of total consumption), antiviral & heterocyclic drug synthesis (≈30‑35 %), pharmaceutical intermediate manufacturing (≈15‑20 %), and agrochemical R&D (≈5‑10 %). The compound‘s unique ortho‑methoxy substitution pattern is the key to its utility across these diverse applications.

1. Antibacterial Research & MurA Inhibitor Development (≈35‑40 % of total consumption). 2‑Bromo‑2′‑methoxyacetophenone is an irreversible inhibitor of MurA (UDP‑N‑acetylglucosamine enolpyruvyl transferase), an essential enzyme in bacterial cell wall biosynthesis. The compound covalently modifies the MurA active site and has been shown to inhibit MurA from Escherichia coli with an IC₅₀ value of 0.38 μM, making it approximately 103‑fold more potent than the reference MurA inhibitor MurA‑IN‑2 (IC₅₀ = 39 μM). The ortho‑methoxy directing group is absolutely essential for activity: 2‑bromoacetophenone and 4′‑methoxy regioisomers completely fail to replicate MurA binding, confirming the stringent structure‑activity relationship (SAR) of this scaffold. This high potency positions the compound as a valuable tool for antibacterial drug discovery programs targeting drug‑resistant Gram‑positive and Gram‑negative pathogens.

Beyond direct enzyme inhibition, the compound also serves as a key building block in the synthesis of antibacterial agents belonging to the benzofuran class. It has been shown to be a potent inhibitor against both Gram‑positive and Gram‑negative bacteria, acting by binding to the pyridinium ring of DNA gyrase, thereby inhibiting DNA replication and transcription, preventing the production of new proteins and causing cell death by apoptosis or necrosis.

2. Antiviral & Heterocyclic Drug Synthesis (≈30‑35 % of total consumption). The compound is directly used as a reagent in the synthesis of 3‑biphenylimidazo[1,2‑a]pyridines and [1,2‑b]pyridazines, which have been identified as novel inhibitors of the Flaviviridae family of viruses, including hepatitis C virus (HCV) and other emerging flaviviruses. The ortho‑methoxy directing group is essential for the correct regiochemistry of the cyclisation; the 4′‑methoxy isomer yields products that fall outside the scope of the patent claims. The high purity grades available (≥98‑99 %) ensure consistent, reproducible cyclisation yields in multi‑step antiviral API syntheses.

The compound‘s bromoacetyl group is a versatile handle for constructing diverse heterocyclic pharmacophores. It can undergo nucleophilic substitution with amines, thiols and other nucleophiles to generate libraries of substituted acetophenone derivatives for high‑throughput screening in antiviral drug discovery campaigns.

3. Pharmaceutical Intermediate Manufacturing (≈15‑20 % of total consumption). 2‑Bromo‑2′‑methoxyacetophenone is widely used as a versatile pharmaceutical intermediate in the synthesis of various drug candidates and bioactive molecules. The reactive bromoacetyl group can be transformed into ketones, alcohols, ethers and esters, making it a flexible building block for constructing complex molecular architectures. The compound can also be used to synthesise other pharmaceutical intermediates and active pharmaceutical ingredients (APIs). Several patent families have cited the compound as a key starting material, including applications covering piperazine‑containing ferulic acid derivatives for CNS disorders, citral thiazole hydrazone derivatives with antimicrobial activity, pyrazolotriazines as kinase inhibitors, substituted aminoquinolones as DGKα inhibitors for immune activation, and mutant IDH inhibitors for cancer therapy.

4. Agrochemical R&D (≈5‑10 % of total consumption). The compound‘s ability to inhibit bacterial enzymes and its robust heterocyclic framework have attracted interest in agrochemical research, particularly for the development of novel crop protection agents. It is used as a building block in the synthesis of herbicidal and fungicidal compounds that interfere with essential bacterial or fungal pathways. Its stable, well‑characterised structure and predictable reactivity make it an ideal starting point for agrochemical lead optimisation.

5. Material Science & Organic Electronics (≈5 % of total consumption). 2‑Bromo‑2′‑methoxyacetophenone is used as a precursor for functionalised aromatic compounds in advanced material applications, including the preparation of covalent organic frameworks (COFs), metal‑organic frameworks (MOFs) and specialty polymers with tailored electronic properties.

Market Size, Supply & Pricing

The global market for 2‑bromo‑2′‑methoxyacetophenone is expanding at a CAGR of approximately 5‑7 %, driven by the compound‘s critical role in antibacterial and antiviral drug discovery. The increasing focus on novel antibacterial agents acting via the MurA pathway, combined with the growing demand for heterocyclic building blocks in antiviral API manufacturing, continue to support strong demand growth.

Key international suppliers include AK Scientific (95‑98 % purity), BenchChem (≥98 % purity), BOC Sciences, Sigma‑Aldrich (Aldrich, 98 % purity), Thermo Fisher Scientific (Alfa Aesar, 98 % purity), AbMole (≥98.0 % purity), CymitQuimica (≥95 % purity) and Biozol (USBiological). The compound is generally supplied as a white to off‑white or greyish‑green crystalline solid, with purity ranging from 95 % to ≥98 % (GC or HPLC), melting point 43‑45 °C (lit.), MDL MFCD00000196, EINECS 250‑870‑2. Storage conditions: 2‑8 °C, under inert atmosphere, in sealed, light‑protected containers.

Pricing varies by quantity and supplier. For R&D quantities (1‑5 g), the compound is typically priced at approximately USD 30‑50 per gram; for bulk industrial orders (25 g, 100 g, 500 g, 1 kg and above), custom pricing is available upon request.

Regional Market Dynamics

Asia‑Pacific, and China in particular, is the largest and fastest‑growing region for both production and consumption of 2‑bromo‑2′‑methoxyacetophenone. Chinese manufacturers have established dedicated large‑scale bromination and purification facilities, producing high‑purity material at competitive prices. India‘s rapidly expanding generic pharmaceutical and agrochemical API sector also drives significant volume demand.

North America and Europe command the largest share of high‑purity R&D consumption (≥98‑99 %), driven by the highest concentration of antibacterial (MurA‑targeting), antiviral (Flaviviridae inhibitor) and cancer drug discovery programmes, as well as advanced agrochemical innovation. Customer requirements in these regions are stringent: documented purity by GC/HPLC, full traceability, heavy metals analysis (≤10 ppm, ICH Q3D), residual solvents by GC‑headspace, and stability data for long‑term storage.

Japan and the Republic of Korea demand ultra‑high‑purity grades for advanced pharmaceutical development and high‑performance material science applications.

Storage, Stability & Regulatory Considerations

2‑Bromo‑2′‑methoxyacetophenone (CAS 31949‑21‑0) is classified as a Corrosive (C) hazardous substance with UN number UN 3261, hazard class 8, packing group II. GHS hazard statements: H314 (Causes severe skin burns and eye damage), H318 (Causes serious eye damage). The compound is also a lachrymator, and exposure should be avoided. Precautionary statements: P260 (Do not breathe dusts or mists), P264 (Wash skin thoroughly after handling), P280 (Wear protective gloves/clothing/eye protection/face protection), P301+P330+P331 (If swallowed: rinse mouth. Do NOT induce vomiting), P303+P361+P353 (If on skin: remove contaminated clothing and rinse with water), P305+P351+P338+P310 (If in eyes: rinse cautiously with water, remove contact lenses, continue rinsing and seek medical advice), P363 (Wash contaminated clothing before reuse), P405 (Store locked up) and P501 (Dispose of contents/container to approved waste disposal plant).

The powder is stable for up to three years when stored at –20 °C and for up to two years at 4 °C; stock solutions are stable for up to six months at –80 °C. The compound is stable for a few days during ordinary shipping and time spent in customs. The compound should be stored in a tightly sealed, dry, light‑protected container, kept away from strong oxidising agents and strong bases. A hazmat fee may apply to certain package sizes and shipment methods.

In the European Union, the compound is subject to REACH regulations (EC‑No. 250‑870‑2); importers and manufacturers must provide Safety Data Sheets (SDS). In the United States, it is regulated under TSCA as a research chemical (Note: the compound may not be listed on the TSCA inventory; buyers must verify regulatory status before commercial use); for pharmaceutical API use, adherence to cGMP guidelines (21 CFR Parts 210/211) is required. In China, the compound is listed in the Inventory of Existing Chemical Substances (IECSC) with customs HS code 2914700090 and requires safety production licences for manufacturing facilities.

Future Outlook

The market outlook for 2‑bromo‑2′‑methoxyacetophenone is tied to four core drivers: (1) the continued expansion of the global antibacterial market, with increasing focus on novel MurA‑targeting agents to combat drug‑resistant pathogens; (2) the sustained development of Flaviviridae inhibitors (HCV, dengue, Zika, emerging flaviviruses) that rely on the ortho‑methoxy bromoacetyl scaffold for correct heterocyclic regiochemistry; (3) the rapid growth of Asian CRO/CDMO sectors supplying intermediates to global pharmaceutical and agrochemical companies; and (4) the increasing adoption of the compound in heterocyclic drug discovery, material science and agrochemical research.

Shanghai XinChem Co., Ltd. (XinChem)

As a world‑leading supplier of pharmaceutical intermediates, bromoacetophenone derivatives and fine chemicals, Shanghai XinChem Co., Ltd. (XinChem) has always focused on the innovative needs of the pharmaceutical, agrochemical and material science industries. Relying on core advantages in bromination chemistry, heterocyclic synthesis and rigorous quality assurance, we provide high‑quality 2‑Bromo‑2′‑methoxyacetophenone (o‑Methoxyphenacyl bromide, CAS 31949‑21‑0) to global customers.

1. Technical Advantages

High Purity & Consistency: Our product achieves purity ≥98‑99 % (GC/HPLC), white to off‑white crystalline powder, molecular weight 229.07 g/mol, melting point 43‑45 °C, MDL MFCD00000196, and moisture <0.5 % (KF titration). Each batch is tested for bromoacetyl content to ensure reliable reactivity in nucleophilic substitution and cyclisation reactions.
Low Impurity Profile: Strict control of residual solvents (<0.5 % total), heavy metals (≤10 ppm, ICH Q3D compliant), residual brominating agents and related substances by HPLC‑UV ensures high synthetic performance for pharmaceutical, agrochemical and material science applications.
Pharmaceutical‑Grade Quality: The compound is tested for full ICH Q3C (residual solvents) and ICH Q3D (heavy metals), and is available with DMF support for pharmaceutical intermediate customers.
Batch‑to‑Batch Uniformity: Rigorous analytical testing (GC, HPLC, NMR, LC‑MS, heavy metals by ICP‑MS, residual solvents by GC‑headspace, Karl Fischer titration) guarantees consistent quality and reproducible yields across all production lots.

2. Product Advantages

Versatile Bromoacetyl Scaffold with Ortho‑Methoxy Directing Group: Directly used as a key building block for MurA‑targeting antibacterials (IC₅₀ = 0.38 μM), 3‑biphenylimidazo[1,2‑a]pyridines and [1,2‑b]pyridazines (Flaviviridae inhibitors), heterocyclic pharmacophores, pharmaceutical intermediates and bioactive molecules.
Proven Potency & Regiocontrol: The ortho‑methoxy group is essential for MurA binding and correct heterocyclic cyclisation; 4′‑methoxy and unsubstituted regioisomers are inactive and yield incorrect regiochemistry.
Flexible Packaging Options: 1 g, 5 g, 10 g, 25 g, 50 g, 100 g, 500 g, 1 kg glass bottles/HDPE containers (R&D/pilot); 5 kg, 10 kg, 25 kg, 50 kg HDPE drums/fiber drums (industrial). Full custom packaging available for pharmaceutical, agrochemical and material science campaigns.
Reliable Supply Chain: Annual capacity in the multi‑metric‑ton range, with dedicated temperature‑controlled warehousing (2‑8 °C, under inert gas, dry, light‑protected, sealed containers) and just‑in‑time delivery capabilities.

3. Application Fields

Pharmaceutical Intermediates: Key building block for MurA inhibitors (antibacterials targeting drug‑resistant pathogens), Flaviviridae inhibitors (HCV, dengue, Zika), heterocyclic drug candidates, piperazine‑containing ferulic acid derivatives, citral thiazole hydrazone derivatives, pyrazolotriazines (kinase inhibitors), substituted aminoquinolones (DGKα inhibitors), and mutant IDH inhibitors (cancer therapy).
Antibacterial Research: Direct MurA inhibitor (IC₅₀ = 0.38 μM, E. coli), SAR lead for novel Gram‑positive and Gram‑negative antibiotics, DNA gyrase inhibitor (benzofuran class).
Agrochemical Intermediates: Building block for herbicides, fungicides and crop protection agents.
Material Science & Organic Electronics: Precursor for covalent organic frameworks (COFs), metal‑organic frameworks (MOFs) and functionalised polymers with tailored electronic properties.
CRO/CDMO Custom Synthesis: Essential custom‑synthesised intermediate for medicinal chemistry outsourcing, hit‑to‑lead optimisation and preclinical synthesis.

4. Service Support
Our technical team provides full impurity profiling (GC purity, HPLC‑UV related substances, residual solvents by GC‑headspace, heavy metals by ICP‑MS, LC‑MS identity confirmation), custom purification to any desired specification, and complete regulatory documentation (Certificate of Analysis, Technical Data Sheet, Safety Data Sheet, REACH compliance, TSCA certification, DMF support for pharmaceutical customers). We also offer custom synthesis of bromoacetophenone derivatives, cold‑chain logistics and just‑in‑time delivery.

5. Why Choose XinChem

Professionalism: 20 + years in the pharmaceutical intermediate, heterocyclic chemistry and fine chemical industries.
Flexibility: Tailored to customer purity specifications, packaging sizes and regulatory documentation requirements.
Cost‑effectiveness: High purity at competitive industrial pricing.

Post time: Jun-07-2026

The Versatile Bromoacetyl Scaffold for MurA-Targeting Antibacterials, Antiviral Agents and Pharmaceutical Synthesis: 2-Bromo-2′-methoxyacetophenone (CAS 31949-21-0)