5-Ethynyl-benzo[1,3]dioxole

Base Information

• Chemical Name: 5-Ethynyl-benzo[1,3]dioxole
• CAS No.: 57134-53-9
• Molecular Formula: C9H6 O2
• Molecular Weight: 146.145
• Hs Code.: 2932999099
• European Community (EC) Number: 260-583-4
• UNII: R5TCC7VX7J
• DSSTox Substance ID: DTXSID60205771
• Nikkaji Number: J349.095E
• Wikidata: Q83079424
• Mol file: 57134-53-9.mol

Synonyms:57134-53-9;5-ETHYNYL-BENZO[1,3]DIOXOLE;5-Ethynylbenzo[d][1,3]dioxole;5-ethynyl-1,3-benzodioxole;5-Ethynylbenzo-1,3-dioxole;1,3-BENZODIOXOLE, 5-ETHYNYL-;EINECS 260-583-4;4-ethynyl-1,2-methylenedioxybenzene;R5TCC7VX7J;5-ethynyl-1,3-dioxaindane;SCHEMBL861172;YSCK0422;DTXSID60205771;MFCD07777106;AKOS005216173;AB42394;5-ETHYNYL-2H-1,3-BENZODIOXOLE;s12364;AS-19739;CS-0147889;FT-0692718;EN300-640746;A913227

Chemical Property of 5-Ethynyl-benzo[1,3]dioxole

Chemical Property:

• Vapor Pressure: 0.148mmHg at 25°C
• Melting Point: 31°C
• Boiling Point: 222.9°Cat760mmHg
• Flash Point: 90.1°C
• PSA: 18.46000
• Density: 1.24g/cm³
• LogP: 1.39660
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 146.036779430
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

98%min ^*data from raw suppliers

5-Ethynylbenzo[d][1,3]dioxole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CC2=C(C=C1)OCO2

Technology Process of 5-Ethynyl-benzo[1,3]dioxole

There total 35 articles about 5-Ethynyl-benzo[1,3]dioxole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

5-<2-(Trimethylsilyl)ethenyl>-1,3-benzodioxole (147771-00-4) → 3,4-methylenedioxyphenylethyne (57134-53-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield: 95.0%

5-(2,2-dibromovinyl)-1,3-benzodioxol (92449-54-2) → 3,4-methylenedioxyphenylethyne (57134-53-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; -78 deg C, 1h, then RT, 1.5 h;

Reference yield: 87.0%

1-chloro-2-(3,4-methylenedioxyphenyl)-1-(p-tolylsulfinyl)-ethene (596118-98-8) → 3,4-methylenedioxyphenylethyne (57134-53-9)

Guidance literature:

1-chloro-2-(3,4-methylenedioxyphenyl)-1-(p-tolylsulfinyl)-ethene; With tert-butylmagnesium chloride; ethylmagnesium chloride; In tetrahydrofuran; at -78 ℃;

With N,N,N,N,N,N-hexamethylphosphoric triamide; PhSO₂C(Li)HPh; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1248/cpb.51.966

upstream raw materials:

3-(benzo[d][1,3]dioxol-5-yl)propiolic acid

aniline

piperonal

(bromomethylene)triphenylphosphorane

Downstream raw materials:

(Z)-5-<1-Bromo-2-(dimethylphenylsilyl)ethenyl>-1,3-benzodioxole

1-(benzo[d][1,3]dioxol-6-yl)ethanone

(4Z,6Z)-3-(Methoxymethoxy)-7-(dimethylphenylsilyl)-6-<(3,4-methylenedioxy)phenyl>-4,6-heptadien-1-ol

(4Z,6Z)-3-(Methoxymethoxy)-7-(dimethylphenylsilyl)-6-<(3,4-methylenedioxy)phenyl>-4,6-heptadienal

Refernces

• 1、 Tian, Ming-Qing,Shen, Zhen-Yao,Zhao, Xuefei,Walsh, Patrick J.,Hu, Xu-Hong. "Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical". supporting information. p. 9706 - 9711. Retrieved 2021/03/19.
• 2、 Trefzger, Ozildéia S.,Barbosa, Natália V.,Scapolatempo, Renata L.,das Neves, Amarith R.,Ortale, Maria L. F. S.,Carvalho, Diego B.,Honorato, Ant?nio M.,Fragoso, Mariana R.,Shuiguemoto, Cristiane Y. K.,Perdomo, Renata T.,Matos, Maria F. C.,Chang, Marilene R.,Arruda, Carla C. P.,Baroni, Adriano C. M.. "Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5-disubstituted isoxazole compounds based on 5-nitrofuran scaffolds". . . Retrieved 2019/12/27.