15727-65-8

Basic information

• Product Name: 1-ETHYNYLNAPHTHALENE
• Synonyms: 1-naphthylacetylene;1-naphthylethyne;Naphthalene, 1-ethynyl-;naphthalene,1-ethynyl-;α-ethynylnaphthalene;(1-Naphtyl)acetylene;1-Ethynylnaphthalene 97%
• CAS NO: 15727-65-8
• Molecular Formula: C₁₂H₈
• Molecular Weight: 152.19
• EINECS: 200-258-5
• Product Categories: Alkynes;Organic Building Blocks;Terminal;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 15727-65-8.mol

Chemical Properties

• Melting Point: 1°C
• Boiling Point: 209.67°C (rough estimate)
• Flash Point: 96 °F
• Appearance: /
• Density: 1.070 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: n20/D 1.6500(lit.)
• CAS DataBase Reference: 1-ETHYNYLNAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYNYLNAPHTHALENE(15727-65-8)
• EPA Substance Registry System: 1-ETHYNYLNAPHTHALENE(15727-65-8)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 15727-65-8(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
1-Ethynylnaphthalene is used as a key intermediate in the synthesis of various organic compounds, such as bis-6,6′-(ethynyl-1-naphthalene)-2,2′-bipyridine. This application is due to its unique structure, which allows for further chemical reactions and the creation of new molecules with different properties and potential uses.
2. Used in Research and Development:
1-Ethynylnaphthalene may also be utilized in research and development for exploring its chemical properties, reactivity, and potential applications in various industries. Its unique structure and synthetic accessibility make it an interesting candidate for studying new reactions and developing novel compounds.
3. Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 1-Ethynylnaphthalene could potentially be used in the pharmaceutical industry for the development of new drugs or drug candidates. Its unique structure and synthetic versatility may allow for the creation of new molecules with therapeutic properties.
4. Used in Material Science:
1-Ethynylnaphthalene may also find applications in material science, particularly in the development of new materials with specific properties. Its unique structure could be exploited to create materials with improved mechanical, electrical, or optical characteristics.

InChI:InChI=1/C12H8/c1-2-10-7-5-8-11-6-3-4-9-12(10)11/h1,3-9H

Upstream product

• 77150-84-6 (Z)-1-(β-bromovinyl)naphthalene 
• 591-51-5 phenyllithium 
• 67665-33-2 1-(1-chloro-vinyl)-naphthalene 
• 58229-02-0 1-(2,2-Dichloro-1-fluoro-vinyl)-naphthalene 
• 558-13-4 carbon tetrabromide 
• 66-77-3 1-naphthaldehyde 
• 3246-80-8 9-phenyl-9H-xanthene 
• 40888-18-4 2-methyl-4-(1-naphthalen-2-yl)but-3-yn-2-ol 
• 31838-47-8 1-(1-naphthyl)-1,2-dibromoethane 
• 39598-55-5 (bromomethylene)triphenylphosphorane 
• 104784-51-2 1-(trimethylsilyl)ethynylnaphthalene 
• 85924-92-1 1-methylene-1H-cyclobutanaphthalene 
• 16176-23-1 3-(naphthalen-1-yl)propiolaldehyde 
• 90-14-2 1-Iodonaphthalene 

Downstream Products

• 24148-98-9 1-Phenyl-3-<1>naphthyl-propin-1-on-oxim 
• 108213-37-2 2,5-dichloro-3,6-diethoxy-4-hydroxy-4-(1-naphthylethynyl)-2,5-cyclohexadienone 
• 3246-80-8 9-phenyl-9H-xanthene 
• 941-98-0 1'-naphthacetophenone 
• 293744-63-5 N-Methyl-2-naphthalen-1-ylethynyl-benzamide 
• 604-53-5 1,1'-bisnaphthalene 
• 72735-70-7 2-(4-methylphenyl)ethynylnaphthalene 
• 221910-11-8 2-[2-(1-naphthyl)ethynyl]benzenamine 
• 914675-27-7 (S)-2,2-dimethyl-4-[3-(naphthalen-1-ylethynyl)benzyloxymethyl]-1,3-dioxolane 
• 923026-47-5 4-naphthalen-1-yl-1-[(3-phenylprop-2-yn-1-yl)oxy]but-3-yn-2-one 

Relevant articles and documents

Substituted Tetraethynylethylene–Tetravinylethylene Hybrids

A general synthetic approach to molecular structures that are hybrids of tetraethynylethylene (TEE) and tetravinylethylene (TVE) is reported. The synthesis permits the controlled preparation of many previously inaccessible structures, including examples w

Nickel-Catalyzed Decarbonylative Cycloaddition of Benzofuran-2,3-diones with Alkynes to Flavones

Using dppe as the ligand, the Nickel-catalyzed decarbonylative cycloaddition of benzofuran-2,3-diones with alkynes was established, and a variety of functional flavones were synthesized in 65–99% yields. Terminal alkynes with substituted phenyl groups and internal alkynes such as aryl acyl acetylenes and diphenylacetylenes are suitable for this reaction. The effects of bases on the reactions of different types of alkyne substrates were also investigated and discussed. (Figure presented.).

Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical

Direct oxidative C(sp)?H/C(sp3)?H cross-coupling offers an ideal and environmentally benign protocol for C(sp)?C(sp3) bond formations. As such, reactivity and site-selectivity with respect to C(sp3)?H bond cleavage have remained a persistent challenge. Herein is reported a simple method for iron-catalyzed/silver-mediated tertiary alkylation of terminal alkynes with readily available and versatile 1,3-dicarbonyl compounds. The reaction is suitable for an array of substrates and proceeds in a highly selective manner even employing alkanes containing other tertiary, benzylic, and C(sp3)?H bonds alpha to heteroatoms. Elaboration of the products enables the synthesis of a series of versatile building blocks. Control experiments implicate the in situ generation of a tertiary carbon-centered radical species.

Polycyclic aromatic hydrocarbon-substituted push-pull chromophores: An investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches

A series of new push-pull chromophores were synthesized in moderate to very high yields (65%-97%) by treating TCNE and TCNQ with alkynes substituted by electron-rich diethylaniline and polycyclic aromatic hydrocarbons. Some of the chromophores exhibit strong intramolecular charge-transfer bands in the near-IR region with λmax values between 695 and 749 nm. With the help of experimental and theoretical analysis, it is concluded that the trend in λmax values is affected by PAH substituents sterically, not electronically. Steric constraints led to the increased dihedral angles, reducing conjugation efficiencies. The absorption properties of push-pull compounds have been investigated in solvents possessing different polarities. All chromophores exhibited positive solvatochromism. As an additional proof of efficient charge-transfer in push-pull chromophores, quinoid character (dr) values were predicted using calculated bond lengths. Remarkably, substantial dr values (0.045-0.049) were predicted for donor diethylaniline rings in all compounds. The effects of various polycyclic aromatic hydrocarbons on optical and nonlinear optical properties were also studied by computational methods. Several parameters, such as band gaps, Mulliken electronegativity, chemical hardness and softness, dipole moments, average polarizability, first hyperpolarizability, were predicted for chromophores at the B3LYP/6-31++G(d,p) level of theory. The predicted first hyperpolarizability β(tot) values vary between 198 to 538 × 10-30 esu for the reported push-pull chromophores in this study. The highest predicted β(tot) value in this study is 537.842 × 10-30 esu, 8150 times larger than the predicted β(tot) value of benchmark NLO material urea, suggests possible utilization of these chromophores in NLO devices. The charge-transfer character of the synthesized structures was further confirmed by HOMO-LUMO depictions and electrostatic potential maps.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea

Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block

A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.

Synthesis of alkynes under dry reaction conditions

An easy synthetic method was developed under dry reaction conditions for the preparation of terminal alkynes from 1,1-dibromoalkenes and in the presence of succinimide which acts as a nucleophile and proton donor. It was demonstrated with the synthesis of a broad spectrum of terminal alkynes and extended to synthesize internal alkynes under tandem reaction conditions.

Electrochemical Synthesis of 1-Naphthols by Intermolecular Annulation of Alkynes with 1,3-Dicarbonyl Compounds

C-centered radical cyclization under electrochemical conditions is a feasible strategy for constructing cyclic structures. Reported herein is the electrochemical synthesis of highly functionalized 1-naphthols using alkynes and 1,3-dicarbonyl compounds by

Tertiary amines acting as Alkyl radical equivalents enabled by a P/N heteroleptic Cu(I) photosensitizer

An unprecedented exploration of tertiary amines as alkyl radical equivalents for cross-coupling with aromatic alkynes to access allylarenes has been achieved by a P/N heteroleptic Cu(I)based photosensitizer under photoredox catalysis conditions. Mechanist

Copper-Mediated Deacylative Coupling of Ynones via C-C Bond Activation under Mild Conditions

The intermolecular deacylative coupling of unstrained ynones via C-C bond activation was accomplished by a CuCl-bpy system under mild reaction conditions. This protocol features facile cleavage of the C-C bond at room temperature, broad substrate scope, and efficient construction of important symmetric and unsymmetrical 1,3-diyne adducts through homo or cross coupling of ynones, respectively. The preliminary mechanistic investigations indicated that an acyl copper(III) complex is likely involved in this process.