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2,5-dichloroquinoline
  • 2,5-dichloroquinoline2,5-dichloroquinoline

2,5-dichloroquinoline

Model: 59412-12-3
2,5-dichloroquinoline (molecular formula: C₉H₅Cl₂N, molecular weight: 198.05 g/mol) is a halogenated quinoline derivative that serves as a valuable building block in medicinal chemistry and organic synthesis. The compound features a quinoline core with chlorine atoms at the 2‑ and 5‑positions. This substitution pattern significantly influences the molecule‘s electronic properties and provides two reactive handles for further functionalization via cross‑coupling reactions (Suzuki, Buchwald‑Hartwig, Ullmann, etc.) or nucleophilic aromatic substitution.

2,5-dichloroquinoline itself is a privileged scaffold present in numerous bioactive molecules, including antimalarials (chloroquine, mefloquine), antibacterials (fluoroquinolones), and anticancer agents. The introduction of chlorine atoms in 2,5-Dichloroquinoline enhances metabolic stability and lipophilicity while offering orthogonal sites for diversification. 2,5-Dichloroquinoline is typically obtained as an off-white to pale yellow solid (melting point 76–77 °C) and is stable when stored under inert atmosphere at 2–8 °C. Its predicted pKa of –0.77±0.50 reflects the basicity of the quinoline nitrogen, which is significantly reduced by the electron-withdrawing chlorines, a property that makes 2,5-Dichloroquinoline particularly useful for designing metabolically stable drug candidates.


Product Parameters (2,5-Dichloroquinoline, CAS 59412-12-3)

Parameter

Specification

CAS

59412-12-3

Molecular Formula

C₉H₅Cl₂N

Molecular Weight

198.05 g/mol

Purity (HPLC)

≥97% – ≥98% (≥99% reference grade available)

Appearance

Off-white to pale yellow solid

Melting Point

76–77 °C (hexane)

Boiling Point

304.0±22.0 °C (predicted)

Density

1.407±0.06 g/cm³ (predicted)

pKa

–0.77±0.50 (predicted)

Storage

Under inert gas (nitrogen or argon), at 2–8 °C

Stability

Stable when stored as recommended; protect from moisture and air

HS Code

2933499090

Application

Pharmaceutical intermediate, organic synthesis building block


Why Choose Cosperpharm for 2,5-dichloroquinoline?

● Reaction‑ready quality – Our 2,5‑dichloroquinoline is produced via a validated two‑step route (oxidation of 5‑chloroquinoline followed by chlorination with POCl₃), ensuring low residual metals and consistent substitution pattern.

● Scalable for your timeline – From 10 g for a screening library to 100 kg for a pilot campaign – we adapt to your phase.

● Strict inert storage – Each batch is packed under argon to prevent moisture pick‑up and shipped with a desiccant.

● Full traceability – Every delivery includes a CoA with HPLC purity, and we can provide NMR/MS data on request.

● Regulatory ready – As a licensed exporter, we support your DMF, IND, or ANDA filings with appropriate documentation.


Typical Preparation Route (for reference)

2,5-Dichloroquinoline is commonly prepared from 5‑chloroquinoline via N‑oxidation followed by chlorination:

Step 1: 5‑Chloroquinoline (30 g, 183 mmol) is treated with m‑CPBA (39 g, 192 mmol) in DCM at 15 °C for 12 h, quenched with Na₂SO₃ solution, and extracted. The crude product is purified by column chromatography to give the N‑oxide intermediate (yield ~49%).

Step 2: The N‑oxide (19 g, 106 mmol) is reacted with POCl₃ (32 g, 212 mmol) in DCM at 40 °C for 1.5 h. After aqueous work‑up and purification, 2,5‑dichloroquinoline is obtained as a white solid (yield ~40%).

This route is reliable and can be scaled up under controlled conditions.


Storage & Handling Recommendations

● Storage: Keep under inert atmosphere (nitrogen or argon) at 2–8 °C in a tightly sealed container. Avoid exposure to air, moisture, and strong oxidants.

● Stability: Stable for at least 24 months when stored as recommended.

● Handling: Use in a fume hood with standard PPE (gloves, goggles, lab coat). The compound may be an irritant – avoid inhalation and skin contact.


Contact us

Interested in 2,5-Dichloroquinoline (CAS 59412‑12‑3)? We make it easy to get started.

● Request a sample – small quantities shipped within a week.

● Ask for a quote – competitive pricing, any volume.

● Custom documentation – CoA, MSDS, NMR, or special packaging.

● Technical discussion – our chemists can help with application advice.

Simply email or call us – tell us what you need, and we’ll take care of the rest. Cosperpharm is here to be your long‑term, reliable partner for 2,5‑dichloroquinoline and other heterocyclic intermediates.


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