6-Methoxy-2-vinylnaphthalene

Model: 63444-51-9

6-Methoxy-2-vinylnaphthalene features a naphthalene backbone with a methoxy group (–OCH₃) at the 2‑position and a vinyl group (–CH＝CH₂) at the 6‑position. Its molecular formula is C₁₃H₁₂O, with a molecular weight of 184.23 g/mol, and it appears as a white to light yellow crystalline powder. The methoxy group enhances solubility in organic solvents, while the vinyl group provides a reactive site for key transformations such as hydroformylation, hydroesterification, and polymerization.

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Product Description

6-Methoxy-2-vinylnaphthalene is the critical starting material for the synthesis of Naproxen — one of the most widely used non‑steroidal anti‑inflammatory drugs (NSAIDs) worldwide. The vinyl side chain of 6‑Methoxy‑2‑vinylnaphthalene can be functionalized to introduce the propionic acid moiety that defines the Naproxen structure. Researchers have developed multiple catalytic routes from 6‑Methoxy‑2‑vinylnaphthalene to Naproxen, including:

● Hydroformylation‑oxidation: MVN (abbreviation for 6‑Methoxy‑2‑vinylnaphthalene) undergoes hydroformylation using Rh(CO)₂(acac) catalyst with dppe ligand, achieving >98% selectivity to the aldehyde precursor 2‑(6‑methoxynaphthyl)propanal (2‑MNP); subsequent oxidation using Na₂WO₄/H₂O₂ yields Naproxen with >80% selectivity.

● Hydroesterification: Pd complexes containing chelating nitrogen ligands (e.g., 2‑acetylpyridine) convert 6‑Methoxy‑2‑vinylnaphthalene directly to the methyl ester of Naproxen, with the best catalyst achieving a turnover frequency of 42 h⁻¹.

Beyond pharmaceutical synthesis, this compound is utilized in materials science (especially in the development of organic solar cells), asymmetric catalysis (enantioselective hydrocyanation processes), and coordination chemistry (as a bidentate ligand in palladium complexes).

Product Parameters

Parameter	Specification
CAS Number	63444-51-9
Molecular Formula	C₁₃H₁₂O
Molecular Weight	184.23 g/mol
Melting Point	88–91 °C
Appearance	White to light yellow powder to crystal
Physical Form	Solid
HS Code	29093090
Canonical SMILES	COC1=CC2=C(C=C1)C=C(C=C2)C=C
Safety Statements	S24/25: Avoid contact with skin and eyes
Purity	≥98.0% (GC)

Why Cosperpharm? – Our Competitive Advantages

Advantage	Detail
Production Strength	GMP-certified campus spanning 100+ mu, 3 multi-purpose workshops, 6 D-grade clean zone production lines, and 150+ reactors (20L–5000L), supporting high/low temp, anaerobic & hydrogenation; kg to ton scale production.
Fast Delivery	R&D samples: one week; commercial orders: 1–2 months after payment. Express (DHL/FedEx) or air/sea freight available.
Global Partners	Trusted by 30+ pharmaceutical companies in USA, Europe, India, Brazil, and Southeast Asia; long-term cooperation with generic drug manufacturers, CROs, and impurity standard distributors.
Licensed Exporter	Valid drug import/export license — no compliance delays.
Dual Quality Grades	Both research/pharma grade（≥98%）and high-purity impurity grade（≥99%）available to meet diverse customer needs.

Product Advantages

Advantage	What It Means for You
Direct route to Naproxen	The vinyl group is perfectly positioned for catalytic introduction of the propionic acid side chain — the pharmacophore of this blockbuster NSAID.
High regioselectivity	Hydroformylation using Rh(CO)₂(acac)/dppe achieves >98% selectivity to the desired aldehyde precursor, minimizing purification overhead.
Multiple catalytic pathways	Supports both rhodium-catalyzed hydroformylation and palladium-catalyzed hydroesterification, giving process chemists flexibility in route design.
Stable crystalline solid	Unlike many vinyl monomers that are oils or require stabilizers, MVN is a solid with a sharp melting point (88–91 °C), easy to weigh, handle, and purify.
Environmentally benign synthesis route	The hydroformylation-oxidation sequence uses H₂O₂ as the terminal oxidant and recyclable tungsten catalysts, offering a greener alternative to traditional stoichiometric oxidations.
Beyond pharmaceuticals	Serves as a versatile building block in materials science (organic solar cells), asymmetric catalysis, and coordination chemistry.

Frequently Asked Questions (FAQ)

Q1: Is 6-Methoxy-2-vinylnaphthalene the same as 2‑methoxy‑6‑vinylnaphthalene?

A: Yes. Both names refer to the same compound. The numbering is interchangeable — the methoxy group is at the 2‑position and the vinyl group at the 6‑position.

Q2: What is the primary application of this compound?

A: MVN is used as a key intermediate in the synthesis of Naproxen (a widely used NSAID for pain and inflammation). The vinyl group undergoes hydroformylation or hydroesterification to introduce the propionic acid side chain that defines the Naproxen structure.

Contact Cosperpharm — Your Trusted Source for Naproxen Intermediates

Developing a Naproxen process or exploring new catalytic transformations? Cosperpharm supplies 6-Methoxy-2-vinylnaphthalene (CAS 63444‑51‑9) with ≥98% purity, full analytical documentation, and flexible packaging options. Our team understands the critical role of high‑quality starting materials in pharmaceutical process development and can support your work from laboratory R&D to commercial scale.

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