1-(3-broMo-4-(broMoMethyl)phenyl)ethanone

1-(3-Bromo-4-(bromomethyl)phenyl)ethanone (CAS 909190-70-1), also known as 3'-bromo-4'-(bromomethyl)acetophenone, is a multi‑substituted aromatic ketone that serves as a valuable synthetic building block in organic synthesis, medicinal chemistry, and pharmaceutical research. The molecular formula is C₉H₈Br₂O with a molecular weight of 291.97 g/mol, and the compound is typically supplied as a solid at purities ranging from 95% to 99%.

In pharmaceutical research, 1-(3-bromo-4-(bromomethyl)phenyl)ethanone has been identified as a key intermediate and impurity in the synthesis of the sphingosine‑1‑phosphate (S1P) receptor modulator Siponimod (marketed as Mayzent for the treatment of secondary progressive multiple sclerosis). It is officially registered as Siponimod Impurity 69 and is supplied with detailed characterization data compliant with regulatory guidelines, enabling analytical method development, method validation (AMV), quality control (QC), and ANDA applications. Siponimod itself is a potent and selective S1P1/S1P5 receptor agonist, and 1-(3-bromo-4-(bromomethyl)phenyl)ethanone plays a critical role in the synthetic pathway of this drug.

The compound has also demonstrated significant anticancer potential. Preliminary studies indicate that its derivatives exhibit cytotoxic effects against various cancer cell lines. For example, a related chlorinated analogue has shown strong activity against HCT-116 colon cancer (IC₅₀ = 2.9 μM) and MCF-7 breast cancer (IC₅₀ = 4.27 μM). A thiazole derivative incorporating a similar brominated scaffold induced apoptosis in A549 lung cancer cells via caspase‑3 activation (3.5‑fold at 20 μM) and inhibited AKT/mTOR phosphorylation (60% reduction at 10 μM).

In fine chemical synthesis, 1-(3-bromo-4-(bromomethyl)phenyl)ethanone is extensively used as a research chemical for pharmaceutical development, serving as an analytical standard for HPLC, a building block for constructing more complex bioactive molecules, and a versatile intermediate for polymer and specialty chemical applications.

Product Parameters

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Frequently Asked Questions (FAQ)

Q1: What are the primary applications of 1-(3-Bromo-4-(bromomethyl)phenyl)ethanone?

A: It is primarily used as Siponimod Impurity 69 (official reference standard) for quality control of the multiple sclerosis drug Siponimod (Mayzent), as a multi‑halogenated building block in medicinal chemistry (anticancer and anti‑inflammatory agents), as an analytical reference standard for HPLC, and as an intermediate in the synthesis of pharmaceutical compounds.

Q2：What is the role of this compound in Siponimod synthesis?

A: 1-(3-Bromo-4-(bromomethyl)phenyl)ethanone is a key intermediate and a process‑related impurity in the manufacturing of Siponimod (Mayzent), a potent selective S1P1/S1P5 receptor agonist used for the treatment of secondary progressive multiple sclerosis (SPMS). It is officially registered as Siponimod Impurity 69 and is used as a reference standard for analytical method development, QC, and ANDA applications.

Storage Conditions

● Temperature: Sealed in dry, 2–8°C (refrigerated). For long‑term storage, keep in a cool, dry place. Do not freeze.

● Container: Airtight, tightly sealed container (glass preferred)

● Atmosphere: Store under inert gas (nitrogen or argon) — the bromomethyl group is moisture‑sensitive.

● Light Protection: Protect from light.

● Desiccation: Keep in a dry environment; exposure to moisture may cause hydrolysis of the bromomethyl group.

● Incompatibilities: Strong oxidizing agents, strong bases, strong acids, nucleophiles, and moisture.

● Stability: Stable when stored under inert gas at recommended temperatures for up to 24 months.

● Stock Solution Storage: Prepare solutions in anhydrous DMSO or DMF. Store at –20°C in single‑use aliquots; use within 1 month.

● DOT/IATA Transport: Not hazardous material under normal transport conditions.

Handling recommendation: The compound is moisture‑sensitive and may cause severe burns. Always handle in a well‑ventilated fume hood. Wear appropriate PPE: chemical‑resistant gloves (nitrile or neoprene, double‑gloving recommended), safety goggles, lab coat, and a face shield when handling larger quantities. Avoid generating dust. After opening, purge the container with dry inert gas and reseal tightly. Return to refrigerated storage promptly. In case of skin contact, wash immediately with plenty of water and seek medical attention. In case of eye contact, rinse cautiously with water for at least 15 minutes and seek medical advice. Safety data sheet (SDS) is available upon request.

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