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
• Article Data: 110

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

Chemical Properties

Colourless to Pale Green Liquid

Uses

Different sources of media describe the Uses of 826-74-4 differently. You can refer to the following data:
1. A precursor of polynuclear aromatic hydrocarbons in tobacco smoke.
2. 1-Vinylnaphthalene is used as a precursor of polynuclear aromatic hydrocarbons in tobacco smoke. It is also used as pharmaceutical intermediate.
3. 1-Vinylnaphthalene may be used in the synthesis of 1-naphthyl-1,2-ethanediol, which can further be utilized as a metal hydrogenated catalyst. It may also be used as a substrate material to produce azidocyanation based products.

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

• 773-99-9 2-naphthaleneethanol 
• 60-29-7 diethyl ether 
• 75-07-0 acetaldehyde 
• 703-55-9 1-naphthylmagnesiumbromide 
• 593-60-2 Vinyl bromide 
• 41332-02-9 2-α-naphthylethyl chloride 
• 51463-46-8 dimethyl (α-naphthyl)diazomethylphosphonate 
• 99747-74-7 1-naphthyl triflate 
• 75-11-6 diiodomethane 
• 66-77-3 1-naphthaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 90-11-9 1-Bromonaphthalene 
• 754-05-2 ethenyltrimethylsilane 
• 90-14-2 1-Iodonaphthalene 

Downstream Products

• 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 
• 43017-75-0 1-naphthylacetaldehyde 
• 62222-40-6 2-Naphthalen-1-yl-oxirane 
• 86457-72-9 (-)-1-vinylnaphthalene oxide 
• 91-20-3 naphthalene 
• 827-54-3 2-naphthylethylene 
• 83-32-9 acenaphthene 
• 90-12-0 1-Methylnaphthalene 

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.

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.