827-54-3

Basic information

• Product Name: 2-Vinylnaphthalene
• Synonyms: Naphthalene,2-vinyl- (8CI);(2-Naphthyl)ethylene;(Naphthalen-2-yl)ethene;2-Ethenylnaphthalene
• CAS NO: 827-54-3
• Molecular Formula: C₁₂H₁₀
• Molecular Weight: 154.2078
• EINECS: 212-573-6
• Mol File: 827-54-3.mol

Chemical Properties

• Melting Point: 63-67℃
• Boiling Point: 270.9 °C at 760 mmHg
• Flash Point: 115.5 °C
• Appearance: Tan powder
• Density: 1.031 g/cm³
• Water Solubility: INSOLUBLE
• CAS DataBase Reference: 2-Vinylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Vinylnaphthalene(827-54-3)
• EPA Substance Registry System: 2-Vinylnaphthalene(827-54-3)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R20/22:; R36/38:
• Safety Statements: S26:; S36:
• Hazardous Substances Data: 827-54-3(Hazardous Substances Data)

Usage

Uses

Used in Plastics and Resins Production:
2-Vinylnaphthalene is used as a precursor in the synthesis of various polymers, contributing to the development of plastics and resins. Its unique structure allows for the creation of materials with specific properties tailored for different applications.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 2-Vinylnaphthalene serves as an intermediate in the production of various medications. Its chemical properties make it a valuable component in the synthesis of complex drug molecules.
Used in Fragrance Industry:
2-Vinylnaphthalene is utilized as a monomer for the production of vinyl naphthalene resins, which are essential in the formulation of fragrances. Its distinct floral scent makes it a desirable ingredient in creating a wide range of scents for perfumes and other aromatic products.
However, it is important to note that 2-Vinylnaphthalene is a potential irritant. It can cause skin and eye irritation upon contact and may have harmful effects if inhaled, necessitating proper handling and safety measures during its use in various applications.

InChI:InChI=1/C12H10/c1-2-10-7-8-11-5-3-4-6-12(11)9-10/h2-9H,1H2

Upstream product

• 1485-07-0 naphthalen-2-ethanol 
• 139277-83-1 8-(2-Naphthyl)-7-thianonane-1-thiol 
• 580-13-2 2-bromonaphthalene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 939-27-5 2-ethylnaphthalene 
• 83612-52-6 (E)‐3‐(o‐tolyl)acryloyl chloride 
• 2627-95-4 tetramethyldivinyldisiloxane 
• 90-11-9 1-Bromonaphthalene 
• 74-85-1 ethene 
• 141-97-9 ethyl acetoacetate 
• 93-08-3 methyl 2-naphthyl ketone 
• 25236-64-0 2,2,2-trifluoroethyl methanesulfonate 
• 66-99-9 β-naphthaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 

Downstream Products

• 109699-80-1 benz-1,4-phenanthrenequinone 
• 110773-63-2 2-(2-naphthyl)propanal 
• 439667-97-7 N-(4-tolylsulfonyl)-2-(2-naphthyl)aziridine 
• 66-99-9 β-naphthaldehyde 
• 2039-70-5 (E)-2-styrylnaphthalene 
• 143879-58-7 1-N-acetyl-2-(2-naphthyl)-3-(phenylseleno)indole 

Relevant articles and documents

Functionalized styrene synthesis via palladium-catalyzed C[sbnd]C cleavage of aryl ketones

We report herein the synthesis of functionalized styrenes via palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between aryl ketone derivatives and potassium vinyltrifluoroborate. The employment of pyridine-oxazoline ligand was the key to the cleavage of unstrained C[sbnd]C bond. A variety of functional groups and biologically important moleculars were well tolerated. The orthogonal Suzuki–Miyaura coupling demonstrated the synthetic practicability.

Palladium-Catalyzed Benzylic Silylation of Diarylmethyl Carbonates with Silylboranes under Base-Free Conditions

A palladium-catalyzed benzylic silylation of diarylmethyl carbonates with silylboranes has been developed. The reaction proceeds smoothly even under external base-free conditions, and the corresponding benzylic silanes are formed in good to high yields. The obtained benzyl silane derivatives can work as the benzylic nucleophiles by the action of a suitable fluoride source and react with some carbon electrophiles to deliver the corresponding benzylic C?C cross-coupled products. Additionally, while still preliminary, the allylic silylation of the isoelectronic allylic carbonates is also achieved.

Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent

A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.

N-Methylphenothiazine S-Oxide Enabled Oxidative C(sp2)–C(sp2) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums

Herein, we report the development of a transition-metal-free oxidative C(sp2)–C(sp2) coupling of readily available boronic acids and organolithiums via phenothiazinium ions. Various biaryl, styrene, and diene derivatives were obtained using this reaction system. The key to this process is N-methylphenothiazine S-oxide (PTZSO), which allows efficient conversion of boronic acids to phenothiazinium ions. The mechanism of phenothiazinium formation using PTZSO was investigated using theoretical calculations and experiments, which provided insight into the unique reactivity of PTZSO.

Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings

Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

Electro-mediated PhotoRedox Catalysis for Selective C(sp3)–O Cleavages of Phosphinated Alcohols to Carbanions

We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage of C(sp3)?O bonds of phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which are E-selective and can be made Z-selective in a tandem reduction/photosensitization process where both steps are photoelectrochemically promoted. Spectroscopy, computation, and catalyst structural variations reveal that our new naphthalene monoimide-type catalyst allows for an intimate dispersive precomplexation of its radical anion form with the phosphinate substrate, facilitating a reactivity-determining C(sp3)?O cleavage. Surprisingly and in contrast to previously reported photoexcited radical anion chemistries, our conditions tolerate aryl chlorides/bromides and do not give rise to Birch-type reductions.

Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights

A rhodium-catalyzed denitrogenative formal (3 + 3) transannulation of 1,2,3-thiadiazoles with alk-2-enals is achieved, producing 2,3-dihydrothiopyran-4-ones in moderate to excellent yields. An inverse KIE of 0.49 is obtained, suggesting the reversibility of the oxidative addition of thioacyl Rh(i) carbenes to alk-2-enals. The late-stage structural modifications of steroid compounds are realized. Moreover, our studies show that thioacyl carbenes have different reactivities to those of α-oxo and α-imino carbenes, and highlight the importance of heteroatoms in deciding the reactivities of heterovinyl carbenes.

Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane

We herein disclose the first Ni-catalyzed Hiyama coupling of aryl halides with vinylsilanes. This protocol uses cheap, nontoxic, and stable vinyltrimethoxysilane as the vinyl donor, proceeds under mild and ligand-free conditions, furnishing a diverse variety of styrene derivatives in high yields with excellent functional group compatibility.

Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage

Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.