1-Ethyl-4-ethynylbenzene

Base Information

• Chemical Name: 1-Ethyl-4-ethynylbenzene
• CAS No.: 40307-11-7
• Molecular Formula: C10H10
• Molecular Weight: 130.189
• Hs Code.: 29029090
• European Community (EC) Number: 609-817-2
• DSSTox Substance ID: DTXSID00193320
• Nikkaji Number: J1.737.380C
• Wikidata: Q72476633
• Mol file: 40307-11-7.mol

Synonyms:1-ethyl-4-ethynylbenzene;4-Ethylphenylacetylene;40307-11-7;1-ETHYL-4-ETH-1-YNYLBENZENE;Benzene, 1-ethyl-4-ethynyl-;P-ETHYLPHENYLACETYLENE;MFCD00173887;1-Ethyl-4-ethynyl-Benzene;Ethyl-4-ethynylbenzene;4-ethyl-1-ethynylbenzene;1-Ethynyl-4-ethylbenzene;DTXSID00193320;1-Ethyl-4-ethynylbenzene, 98%;1-ETHYL,4-ETHYNYL-BENZENE;AKOS005146065;AC-4955;CS-W013433;SB66851;AS-14581;SY018461;AM20060617;E0749;FT-0607757;A18741;EN300-103947;J-504607;Z1080385542

Chemical Property of 1-Ethyl-4-ethynylbenzene

Chemical Property:

• Appearance/Colour: White crystal
• Vapor Pressure: 1.04mmHg at 25°C
• Refractive Index: n20/D 1.5420(lit.)
• Boiling Point: 183.7 °C at 760 mmHg
• Flash Point: 53.1 °C
• PSA: 0.00000
• Density: 0.92 g/cm³
• LogP: 2.23030
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 130.078250319
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

99% ^*data from raw suppliers

1-Ethyl-4-ethynylbenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 16-26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=CC=C(C=C1)C#C
• Uses: Intermediates of Liquid Crystals 1-Ethyl-4-ethynylbenzene may be used to synthesize:2,4-bis[(4-ethylphenyl)ethynyl]-6-methoxy-1,3,5-triazine 2-[(4-ethylphenyl)ethynyl]-4-methoxy-6-(phenylethynyl)-1,3,5-triazine 2-chloro-4-[(4-ethylphenyl)ethynyl]-6-methoxy-1,3,5-triazine 4-chloro-6-[(4-ethylphenyl)ethynyl]-N,N-diphenyl-1,3,5-triazin-2-amine

Technology Process of 1-Ethyl-4-ethynylbenzene

There total 8 articles about 1-Ethyl-4-ethynylbenzene 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: 90.0%

(2-(4-ethylphenyl)ethynyl)trimethylsilane (393857-27-7) → 1-ethyl-4-ethynylbenzene (40307-11-7)

Guidance literature:

With potassium trimethylsilonate; In dimethyl sulfoxide; at 70 ℃; for 6h; Sealed tube; Schlenk technique;

DOI:10.1021/acs.joc.7b03139

Reference yield:

4-Ethyl-β,β'-dibromostyrene (59931-57-6) → 1-ethyl-4-ethynylbenzene (40307-11-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; 1.) -78 deg C, 1 h, 2.) r.t., 1 h;

Reference yield:

4-ethyl-1-iodobenzene (25309-64-2) → 1-ethyl-4-ethynylbenzene (40307-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; copper(I) bromide / toluene / 4 h / 20 °C / Inert atmosphere; Schlenk technique

2: potassium carbonate / methanol / 7 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; triethylamine; copper(I) bromide; In methanol; toluene;

DOI:10.1021/ol403684a

upstream raw materials:

4-ethylacetophenone

4-Ethyl-β,β'-dibromostyrene

4-ethylbenzylaldehyde

4-ethyl-1-iodobenzene

Downstream raw materials:

1,4-bis(p-ethylphenyl)buta-1,3-diyne

(E)-1-phenyl-4-(4-ethylphenyl)but-1-en-3-yne

((1E,4E)-5-chloro-5-(4-ethylphenyl)penta-1,4-diene-1,3-diyl)dibenzene

((1E,4E)-5-bromo-5-(4-ethylphenyl)penta-1,4-diene-1,3-diyl)dibenzene

Refernces

• 1、 Buendia, Julien,Darses, Benjamin,Dauban, Philippe. "Tandem catalytic C(sp3)-H amination/sila-sonogashira-hagihara coupling reactions with iodine reagents". supporting information. p. 5697 - 5701. Retrieved 2015/06/16.
• 2、 Xu, Caixia,Du, Weiyuan,Zeng, Yi,Dai, Bin,Guo, Hao. "Reactivity switch enabled by counterion: Highly chemoselective dimerization and hydration of terminal alkynes". supporting information. p. 948 - 951. Retrieved 2014/03/21.