826-74-4

Basic information

• Product Name: 1-VINYLNAPHTHALENE
• Synonyms: naphthalene,1-ethenyl-;α-vinylnaphthalene;ALPHA-VINYLNAPHTHALENE;1-VINYLNAPHTHALENE;1-ETHENYLNAPHTHALENE;1-Vinylnaphthalene (stabilized with TBC);(Naphthalen-1-yl)ethene;1-(1-Naphtyl)ethene
• CAS NO: 826-74-4
• Molecular Formula: C₁₂H₁₀
• Molecular Weight: 154.21
• EINECS: 212-560-5
• Product Categories: Aromatics Compounds;Aromatics;Mutagenesis Research Chemicals;Monomers;NLO MonomersPolymer Science;Non-Linear Optical (NLO) Materials;Photonic and Optical Materials;Vinyl Halides, Amines, Amides, and Other Vinyl Monomers;Naphthalene series
• Mol File: 826-74-4.mol

Chemical Properties

• Melting Point: 322 °C
• Boiling Point: 135-138 °C(lit.)
• Flash Point: 101 °C
• Appearance: liquid
• Density: 1.04 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.653(lit.)
• Storage Temp.: Refrigerator
• Solubility: Soluble in ethyl acetate, hexane and methanol.
• Sensitive: Moisture Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• CAS DataBase Reference: 1-VINYLNAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-VINYLNAPHTHALENE(826-74-4)
• EPA Substance Registry System: 1-VINYLNAPHTHALENE(826-74-4)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-51/53-22
• Safety Statements: 26-36-61
• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 2
• Hazardous Substances Data: 826-74-4(Hazardous Substances Data)

Usage

Uses

Used in Tobacco Industry:
1-VinylNaphthalene is used as a precursor of polynuclear aromatic hydrocarbons in tobacco smoke. It helps in the formation of these harmful compounds that are present in tobacco smoke.
Used in Pharmaceutical Industry:
1-VinylNaphthalene is used as a pharmaceutical intermediate. It is a key component in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medicines.
Used in Chemical Synthesis:
1-VinylNaphthalene may be used in the synthesis of 1-naphthyl-1,2-ethanediol, which can further be utilized as a metal hydrogenated catalyst. This application allows for the production of various chemical compounds and materials.
Used in Azidocyanation Reactions:
1-VinylNaphthalene may also be used as a substrate material to produce azidocyanation-based products. This application is useful in the synthesis of various organic compounds and materials with specific properties and functions.
Chemical Properties:
1-VinylNaphthalene is a colorless to pale green liquid with unique chemical properties. Its molecular structure and reactivity make it a valuable compound in various chemical reactions and applications.

Synthesis Reference(s)

Tetrahedron, 52, p. 915, 1996 DOI: 10.1016/0040-4020(95)00950-7

Purification Methods

Commercial material can contain up to 2% of poly-1-vinylnaphthalene. Fractionally distil it under reduced pressure using a spinning-band column, dry it with CaH2 and again distil it under vacuum. Store it in sealed ampoules in a freezer. It has max (cyclohexane) at 210 and 320nm. The picrate has m 105-106o. [Beilstein 5 H 585, 5 III 1773, 5 IV 1833.] It is an irritant.

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

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 1127-76-0 1-ethylnapthelene 
• 773-99-9 2-naphthaleneethanol 
• 68480-12-6 2-(1,2,3,4-tetrahydronaphthalen-1-yl)ethanol 
• 57605-95-5 1-(1-naphthyl)ethanol 
• 57999-53-8 3-bromo-3-[1]naphthyl-propionic acid 
• 60-29-7 diethyl ether 
• 75-07-0 acetaldehyde 
• 703-55-9 1-naphthylmagnesiumbromide 
• 593-60-2 Vinyl bromide 
• 50-00-0 formaldehyd 
• 23277-00-1 1-naphthylmethyltriphenylphosphonium chloride 
• 75-01-4 chloroethylene 

Downstream Products

• 63084-72-0 (+/-)-(3ar,3bξ,11ac)-3a,3b,11,11a-tetrahydro-phenanthro[1,2-c]furan-1,3-dione 
• 24743-25-7 5,6-Dioxo-5,6-dihydro-picen 
• 62222-40-6 2-(1-naphthyl)oxirane 
• 1127-76-0 1-ethylnapthelene 
• 6636-42-6 (+/-)-1-methyl-1,2,3,4-tetrahydro-phenanthrene-1r,2c-dicarboxylic acid-anhydride 
• 100900-16-1 benz-1,4-phenanthrenequinone 
• 1035-92-3 5-(naphthalen-1-yl)-3-phenyl-4,5-dihydroisoxazole 
• 68323-01-3 Methyl-(2-naphthalen-1-yl-ethyl)-diphenyl-silane 
• 116218-05-4 1-(1’-chloro-2’-phenylethyl)naphthalene 
• 36288-25-2 1-(4-methylphenyl)-2-(naphth-1-yl)ethene 
• 3960-21-2 1,2-di(naphthyl)ethene 
• 90-13-1 1-Chloronaphthalene 
• 81075-98-1 (1S,2R)-2-((S)-Benzyl-phenyl-phosphinoyl)-1,2,3,4-tetrahydro-phenanthrene-1-carboxylic acid methyl ester 
• 81075-99-2 (1R,2S)-2-((S)-Benzyl-phenyl-phosphinoyl)-1,2,3,4-tetrahydro-phenanthrene-1-carboxylic acid methyl ester 

Relevant articles and documents

Tertiary arsine ligands for the Stille coupling reaction

The Stille coupling reaction is one of the most important coupling reactions. It is well known that the triphenylarsine ligand can accelerate the reaction rate of Stille coupling. However, other arsine ligands have never been investigated for the Stille c

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.

Indene formation upon borane-induced cyclization of arylallenes, 1,1-carboboration, and retro-hydroboration

We herein report the reaction of arylallenes with tris(pentafluorophenyl)borane that yields pentafluorophenyl substituted indenes. The tris(pentafluorophenyl)borane induces the cyclization of the allene and transfers a pentafluorophenyl ring in the course of this reaction. A Hammett plot analysis and DFT computations indicate a 1,1-carboboration to be the C-C bond-forming step.

Method for preparing olefin compound under alkaline condition

The invention relates to a method for preparing an olefin compound under an alkaline condition. The method comprises the following steps: adding a solvent and an alkali catalyst into long-chain alcohol serving as a raw material, introducing sulfuryl fluoride gas, stirring for reaction, and separating and purifying to obtain the olefin compound. The olefin compound has a structural formula shown in the description; and in the formula, R is phenyl, substituted phenyl, heterocyclic aryl, fused ring aryl, substituted fused ring aryl or alkyl. An alkali-promoted alcohol-to-olefin conversion method developed by the invention is mild in reaction condition, simple and convenient to operate and low in instrument and equipment requirements, the long-chain alcohol is used as a reaction raw material, the price is low, the source is wide, and the yield of the prepared olefin compound is high; and the method effectively avoids the influence of acidic conditions on part of groups (acetal, ketal, epoxy and the like), is efficient in reaction and wide in substrate application range, can tolerate most of functional groups, and provides a new path for synthesis of complex olefins.

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.

AIR-STABLE NI(0)-OLEFIN COMPLEXES AND THEIR USE AS CATALYSTS OR PRECATALYSTS

The present invention relates to air stable, binary Ni(0)-olefin complexes and their use in organic synthesis.

Iron-Catalyzed Direct Julia-Type Olefination of Alcohols

Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substrate scope (primary and secondary alcohols) functional group tolerance (amino, nitro, halo, alkoxy, thiomethoxy, and S- A nd N-heterocyclic compounds) that can be scaled up. The unprecedented synthesis of 1-methyl naphthalenes proceeds via tandem methenylation/double dehydrogenation. Mechanistic study shows that the cleavage of the C-H bond of alcohol is the rate-determining step.

Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-yl Methyl Sulfone

The methylenation reagent 1-methylbenzimidazol-2-yl methyl sulfone 2 reacts with various aldehydes and ketones in the presence of t-BuOK (room temperature, 1 h) in dimethylformamide to give the corresponding terminal alkenes generally in high yields. For sensitive substrates, the reaction is better carried out at low temperature using sodium hexamethyldisilazide in 1,2-dimethoxyethane. The byproduct is easily removed from the products, and the reaction conditions are mild and practical. Reagent 2 can be easily prepared from commercially available 2-mercaptobenzimidazole 5 in 95% yield without any expensive reagents.

Pyrene-Tagged Alcoholic Ionic Liquids as Phase Transfer Catalysts for Nucleophilic Fluorination

Functional group?activity relationships of pyrene-tagged ionic liquid (PTIL)-based organocatalysts for nucleophilic fluorination using alkali metal fluorides (MFs) are described, which demonstrate that the pyrene, oligoether and alcohol moieties on the imidazolium ring are vital for efficient catalysis. Further investigation of these findings led to the discovery of new strategy, which showed superior catalyst separation process, i.e., catalyst is effortlessly separated from the reaction mixture using reduced graphene oxide. The catalytic efficiency of the PTIL as a phase transfer catalyst was demonstrated by the high conversion of the reactants up to 98% fluorinated yield using MFs in CH3CN or t-amyl alcohol. Importantly, the catalyst not only enhanced the reactivity of bimolecular nucleophilic substitutions (SN2) within a short reaction time and reduces the formation of by-products but also affords high yield with easy isolation and separation under mild conditions.

Carbosulfenylation of Alkenes with Organozinc Reagents and Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate

The electrophilic alkylthiolation of alkenes, initiated by dimethyl(methylthio)sulfonium salts and the subsequent addition of various heteronucleophilies has been well-established. Regarding the use of carbon nucleophiles, however, only carefully designed sp-type carbon sources have been successfully applied. We herein present our findings on the methylthiolation of alkenes with dimethyl(methylthio)sulfonium trifluoromethanesulfonate, followed by carbon-carbon bond formation in the presence of organozinc reagents, thus achieving a catalyst-free protocol toward to the carbosulfenylation of alkenes.