57134-53-9

Basic information

• Product Name: 5-ETHYNYL-BENZO[1,3]DIOXOLE
• Synonyms: 5-ETHYNYL-BENZO[1,3]DIOXOLE;5-Ethynyl-1,3-benzodioxole;Einecs 260-583-4;5-Ethynylbenzo[d][1,3]dioxole
• CAS NO: 57134-53-9
• Molecular Formula: C₉H₆O₂
• Molecular Weight: 146.14
• EINECS: 260-583-4
• Mol File: 57134-53-9.mol

Chemical Properties

• Melting Point: 31°C
• Boiling Point: 222.9°Cat760mmHg
• Flash Point: 90.1°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 0.148mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 5-ETHYNYL-BENZO[1,3]DIOXOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ETHYNYL-BENZO[1,3]DIOXOLE(57134-53-9)
• EPA Substance Registry System: 5-ETHYNYL-BENZO[1,3]DIOXOLE(57134-53-9)

Safety Data

• Hazardous Substances Data: 57134-53-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Ethynyl-benzo[1,3]dioxole is used as a building block for the synthesis of various organic compounds, leveraging its unique structure and reactivity to form a wide range of chemical products.
Used in Materials Science:
In the field of materials science, 5-ethynyl-benzo[1,3]dioxole is utilized as a precursor to functionalized aromatic compounds, contributing to the development of new materials with specific properties.
Used in Organic Electronic Materials:
5-Ethynyl-benzo[1,3]dioxole is used in the development of organic electronic materials due to its potential applications in optoelectronic devices, taking advantage of its aromatic nature and electronic properties.
Used in Pharmaceutical Preparation:
As a starting material, 5-ethynyl-benzo[1,3]dioxole is employed in the preparation of pharmaceuticals, where its unique structure can be leveraged to create novel drug candidates.
Used in Agrochemicals:
5-Ethynyl-benzo[1,3]dioxole also serves as a starting material for the preparation of agrochemicals, where its chemical properties can be harnessed to develop new compounds for agricultural applications.
Used in Organic Semiconductors:
Due to its electronic properties, 5-ethynyl-benzo[1,3]dioxole is used as a component in organic semiconductors, where it can contribute to the performance of these materials in various electronic devices.

InChI:InChI=1/C9H6O2/c1-2-7-3-4-8-9(5-7)11-6-10-8/h1,3-5H,6H2

Upstream product

• 10231-46-6 3-(benzo[d][1,3]dioxol-5-yl)propiolic acid 
• 62-53-3 aniline 
• 120-57-0 piperonal 
• 39598-55-5 (bromomethylene)triphenylphosphorane 
• 994-89-8 tributylethynyltin 
• 109586-40-5 1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate 
• 92449-54-2 5-(2,2-dibromovinyl)-1,3-benzodioxol 
• 64-17-5 ethanol 
• 17207-73-7 2-bromo-1-[3,4-methylenedioxyphenyl]ethylene 
• 51346-95-3 PhSO₂C(Li)HPh 
• 57134-51-7 5-(1,2-dibromo-ethyl)-benzo[1,3]dioxole 
• 634151-51-2 1-benzo[1,3]dioxol-5-yl-2-chloro-2-(toluene-4-sulfinyl)-ethanol 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 

Downstream Products

• 123212-43-1 ({(1R,2R)-2-[(E)-1-Benzo[1,3]dioxol-5-yl-2-(dimethyl-phenyl-silanyl)-vinyl]-2-hydroxy-cyclopentyl}-methyl-amino)-acetonitrile 
• 135191-26-3 (+/-)-cis-2--1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol 
• 150357-74-7 (1S,2S)-N-<(1S)-Methylbenzyl>-N-(cyanomethyl)-1-<(1,3-benzodioxol-5-yl)ethynyl>-2-aminocyclopentanol 
• 131575-70-7 1-bromo-1-(3,4-methylenedioxyphenyl)-2-phenylsulphonylethene 
• 158074-66-9 (Z)-5-<1-Bromo-2-(dimethylphenylsilyl)ethenyl>-1,3-benzodioxole 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 952595-72-1 C₂₄H₂₇NO₄ 
• 791064-77-2 (E)-3-Benzo[1,3]dioxol-5-yl-5-{1-[3-(5-hydroxy-1,4,5,6-tetrahydro-pyrimidin-2-ylamino)-benzoyl]-piperidin-4-yl}-pent-4-enoic acid methyl ester 
• 710947-08-3 4-(4-benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-[1,2,3]triazol-2-yl)-benzonitrile 
• 710946-96-6 4-(4-benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-[1,2,3]triazol-2-ylmethyl)-benzonitrile 
• 158074-77-2 (4Z,6Z)-3-(Methoxymethoxy)-7-(dimethylphenylsilyl)-6-<(3,4-methylenedioxy)phenyl>-4,6-heptadien-1-ol 
• 158074-84-1 (4Z,6Z)-3-(Methoxymethoxy)-7-(dimethylphenylsilyl)-6-<(3,4-methylenedioxy)phenyl>-4,6-heptadienal 

Relevant articles and documents

Anti-inflammatory, ulcerogenic and platelet activation evaluation of novel 1,4-diaryl-1,2,3-triazole neolignan-celecoxib hybrids

This study reports the synthesis of novel neolignans-celecoxib hybrids and the evaluation of their biological activity. Analogs 8–13 (L13-L18) exhibited anti-inflammatory activity, inhibited glycoprotein expression (P-selectin) related to platelet activation, and were considered non– ulcerogenic in the animal model, even with the administration of 10 times higher than the dose used in reference therapy. In silico drug-likeness showed that the analogs are compliant with Lipinski's rule of five. A molecular docking study showed that the hybrids 8–13 (L13-L18) fitted similarly with celecoxib in the COX-2 active site. According to this data, it is possible to infer that extra hydrophobic interactions and the hydrogen interactions with the triazole core may improve the selectivity towards the COX-2 active site. Furthermore, the molecular docking study with P-selectin showed the binding affinity of the analogs in the active site, performing important interactions with amino acid residues such as Tyr 48. Whereas the P-selectin is a promising target to the design of new anti-inflammatory drugs with antithrombotic properties, a distinct butterfly-like structure of 1,4-diaryl-1,2,3-triazole neolignan-celecoxib hybrids synthesized in this work may be a safer alternative to the traditional COX-2 inhibitors.

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.

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5-disubstituted isoxazole compounds based on 5-nitrofuran scaffolds

Nineteen 3,5-disubstituted-isoxazole analogs were synthesized based on nitrofuran scaffolds, by a [3 + 2] cycloaddition reaction between terminal acetylenes and 5-nitrofuran chloro-oxime. The compounds were obtained in moderate to very good yields (45–91%). The antileishmanial activity was assayed against the promastigote and amastigote forms of Leishmania (Leishmania) amazonensis. Alkylchlorinated compounds 14p–r were active on both the promastigote and amastigote forms, with emphasis on compound 14p, which showed strong activity against the amastigote form (IC50 = 0.6 μM and selectivity index [SI] = 5.2). In the alkyl series, compound 14o stands out with an IC50 = 8.5 μM and SI = 8.0 on the amastigote form. In the aromatic series, the most active compounds were those containing electron-donor groups, such as trimethoxy isoxazole 14g (IC50 = 1.2 μM and SI = 20.2); compound 14h, with IC50 = 7.0 μM and SI = 6.1; and compound 14j containing the 4-SCH3 group, with IC50 = 5.7 μM and SI = 10.2. In addition, the antifungal activity of 19 nitrofuran isoxazoles was evaluated against five strains of Candida (C. albicans, C. parapsilosis, C. krusei, C. tropicalis, and C. glabrata). Eleven isoxazole derivatives were active against C. parapsilosis, and compound 14o was found to be the most active (minimal inhibitory concentration [MIC] = 3.4 μM) for this strain. Compound 14p was active against all the strains tested, with an MIC = 17.5 μM for C. glabrata, lower than that of the fluconazole used as the reference drug.

Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N -propargylanilines with diverse carbon pronucleophiles: Facile access to functionalized tetrahydroquinolines

Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with two types of carbon pronucleophiles (nitromethane as a sp3 carbon pronucleophile and phenylacetylenes as sp carbon pronucleophiles) proceeded to give the 2-substituted tetrahydroquinolines in good yields with 100percent atomic utilization without any additional external oxidants.

One-pot synthesis of unsymmetrical 1,3-butadiyne derivatives and their application in the synthesis of unsymmetrical 2,5-diarylthiophenes

A one-pot protocol was developed for the synthesis of unsymmetrical 1,3-butadiynes. The procedure is based on two sequential reactions: deprotection of R–C≡C–C≡C– C(Me)2OH derivatives in a retro-Favorskii reaction to furnish a terminal 1,3-butadiyne compound, which reacted with aryl iod-ides in a Sonogashira-type cross-coupling reaction catalyzed by Pd(PPh3)4 and CuI, using TBAOH as activator and toluene as solvent under reflux for 10 min. We also studied in situ thiocycli-zation of 1,3-butadiynes, leading to unsymmetrical 2,5-diaryl-thiophenes. The principal features of this method are operational simplicity, good substrate scope, very fast reaction, and high yields.

Design, synthesis and antitrypanosomatid activities of 3,5-diaryl-isoxazole analogues based on neolignans veraguensin, grandisin and machilin G

Using bioisosterism as a medicinal chemistry tool, 16 3,5-diaryl-isoxazole analogues of the tetrahydrofuran neolignans veraguensin, grandisin and machilin G were synthesized via 1,3-dipolar cycloaddition reactions, with yields from 43% to 90%. Antitrypanosomatid activities were evaluated against Trypanosoma cruzi, Leishmania (L.) amazonensis and Leishmania (V.) braziliensis. All compounds were selective for the Leishmania genus and inactive against T.?cruzi. Isoxazole analogues showed a standard activity on both promastigotes of L.?amazonensis and L.?braziliensis. The most active compounds were 15, 16 and 19 with IC50 values of 2.0, 3.3 and 9.5?μM against L.?amazonensis and IC50 values of 1.2, 2.1 and 6.4?μM on L.?braziliensis, respectively. All compounds were noncytotoxic, showing lower cytotoxicity (>250?μM) than pentamidine (78.9?μM). Regarding the structure–activity relationship (SAR), the methylenedioxy group was essential to antileishmanial activity against promastigotes. Replacement of the tetrahydrofuran nucleus by an isoxazole core improved the antileishmanial activity.

Method for synthesizing alkyne through catalytic asymmetric cross coupling (by machine translation)

The invention belongs to the field of, asymmetric synthesis, and discloses a method for catalyzing asymmetric cross- coupling to synthesize: an alkyne, and the L method comprises, the following steps, of A: preparing B a cuprous, salt and C a: ligand; preparing a catalyst; adding a base; reacting the compound with the compound with the compound; and reacting the compound with the compound. Of these, one of them, X is selected from the group consisting of, R halogens. 1 Optionally substituted heteroarylsulfonylcyanamide groups selected from the, group consisting, of optionally substituted, phenyl groups In-flight vehicle, R6 Trialkyl silyl groups or alkyl radicals, R2 Cycloalkyl radicals optionally substituted with an, optionally substituted alkyl, (CH radical2 )n R4 Multi,layer chain, n＝0-10,R saw blade4 A group selected, from, the group consisting of phenyl, alkenyl, aralkynyls, noonyloxy,and, noonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylphenyl disiloxy-radicals. R3 A ligand, selected from hydrogen or any of the functional groups, is selected from the group consisting of, hydrogen and any L other functional group. The method, R disclosed by the, A invention has the, advantages of good catalytic, R ’ effect, wide application range. and high catalytic efficiency, and the, method disclosed by the, invention has the. advantages of good catalytic effect, wide application range and high catalytic efficiency. (by machine translation)

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.

COMPOUNDS AND USES THEREOF

The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

Novel method for preparing decumbenine B

The invention provides a novel method for preparing a natural compound decumbenine B. The method comprises the following steps: (i) enabling a compound shown as a formula 4 and a compound shown as a formula 5 to be in contact under a condition suitable for carbon-carbon coupling, so as to generate a compound shown as a formula 3; (ii) carrying out cyclization on the compound shown as the formula 3and ammonium acetate under a suitable condition, so as to generate a compound 2; (iii) enabling the compound shown as the formula 2 and paraformaldehyde to react under the suitable condition, so as to generate the compound decumbenine B shown as a formula 1. (The formula 5, the formula 4, the formula 3, the formula 2 and the formula 1 are shown in the description.).