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 
• 32298-46-7 2,2'-(ethane-1,1-diyl)dinaphthalene 
• 22364-54-1 naphthalen-2-yl(trimethylsilyl)methanone 
• 74-85-1 ethene 
• 450-58-8 2-naphthyldiazonium tetrafluoroborate 
• 64363-88-8 cis-1,2,3,4,4a,9,10,10a-octahydrophenanthrene 
• 3020-28-8 (iodomethyl)triphenylphosphonium iodide 
• 66-99-9 β-naphthaldehyde 
• 139277-83-1 8-(2-Naphthyl)-7-thianonane-1-thiol 
• 580-13-2 2-bromonaphthalene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 91-58-7 2-chloronaphthalene 
• 2876-71-3 methyl 2-naphthylacetate 
• 939-27-5 2-ethylnaphthalene 

Downstream Products

• 65253-81-8 6-Phenyl-5,6-dihydro-benzophenanthren 
• 55024-84-5 naphth[1,2-a]anthracene-9,14-dione 
• 55024-85-6 5-(1,4-Dioxo-1,4-dihydro-naphthalen-2-yl)-naphtho[1,2-a]anthracene-9,14-dione 
• 21461-46-1 (E)-2-(2-nitrovinyl)naphthalene 
• 66-99-9 β-naphthaldehyde 
• 93-09-4 naphthalene-2-carboxylate 
• 27544-18-9 (S)-1-(2-Naphthyl)ethanol 
• 52193-85-8 (R)-1-(2-Naphthyl)ethanol 
• 2017-68-7 2-(naphthalen-2-yl)ethanamine 
• 3082-62-0 (1S)-1-(2-naphthyl)ethylamine 
• 1201-74-7 (R)-[1-(naphthalen-2-yl)ethyl]amine 
• 109699-80-1 benz-1,4-phenanthrenequinone 
• 110773-63-2 2-(2-naphthyl)propanal 
• 136415-67-3 3-(naphthalen-2-yl)propanal 

Relevant articles and documents

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.

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.

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.

Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides

A copper-catalyzed radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides has been developed. The copper-based catalytic system proved crucial for cleavage of the C-C bond of cyclobutanone oximes and for selective C-S bond-formation involving persistent sulfonyl-metal radical intermediates. This protocol is distinguished by the low-cost catalytic system, which does not require ligand, base, or toxic cyanide salt, and by the use of readily accessible starting materials, as well as broad substrate scope, providing an efficient approach to various diversely substituted cyano-containing sulfones.

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

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.

KO-t-Bu Catalyzed Thiolation of β-(Hetero)arylethyl Ethers via MeOH Elimination/hydrothiolation

Herein, we describe a KO-t-Bu catalyzed thiolation of β-(hetero)arylethyl ethers through MeOH elimination to form (hetero)arylalkenes followed by anti-Markovnikov hydrothiolation to afford linear thioethers. The system works well with a variety of β-(hetero)arylethyl ethers, including electron-deficient, electron-neutral, electron-rich, and branched substrates and a range of aliphatic and aromatic thiols.