Ethynyl p-tolyl sulfone

Base Information

• Chemical Name: Ethynyl p-tolyl sulfone
• CAS No.: 13894-21-8
• Molecular Formula: C9H8 O2 S
• Molecular Weight: 180.227
• Hs Code.: 29041000
• European Community (EC) Number: 625-645-0
• ChEMBL ID: CHEMBL234895
• DSSTox Substance ID: DTXSID20403554
• Nikkaji Number: J471.571C
• Mol file: 13894-21-8.mol

Synonyms:Ethynyl p-tolyl sulfone;13894-21-8;1-(ethynylsulfonyl)-4-methylbenzene;Tosylacetylene;Benzene, 1-(ethynylsulfonyl)-4-methyl-;p-Toluenesulfonylacetylene;1-ethynylsulfonyl-4-methylbenzene;1-(ethynesulfonyl)-4-methylbenzene;MFCD00191647;Ethynylp-tolylsulfone;4-(Ethynylsulfonyl)toluene;CHEMBL234895;Ethynyl p-tolyl sulfone, 98%;SCHEMBL1721592;DTXSID20403554;FTHKWIMQNXVEHW-UHFFFAOYSA-N;1-ethynylsulfonyl-2-methyl-benzene;AKOS015840456;AS-63583;SY052661;CS-0134635;E0466;FT-0626366;EN300-114287;F21382;A807465;J-007202

Chemical Property of Ethynyl p-tolyl sulfone

Chemical Property:

• Vapor Pressure: 0.00233mmHg at 25°C
• Melting Point: 73-74 °C(lit.)
• Refractive Index: 1.552
• Boiling Point: 297.9°C at 760 mmHg
• Flash Point: 155.6°C
• PSA: 42.52000
• Density: 1.219g/cm³
• LogP: 2.44020
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: organic solvents: soluble(lit.)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 180.02450067
• Heavy Atom Count: 12
• Complexity: 280

Purity/Quality:

97% ^*data from raw suppliers

Ethynyl p-Tolyl Sulfone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)C#C
• General Description: ETHYNYL P-TOLYL SULFONE (also known as tosylacetylene or p-toluenesulfonylacetylene) is an alkynyl sulfone compound used as a key reactant in metal-free photoredox catalysis for forming C(sp³)-C(sp) bonds. In the described study, it participated in reactions with redox-activated primary amine derivatives, facilitated by Eosin Y photocatalysis under green LED light, to yield functionalized alkynes. Its role highlights its utility as an electrophilic alkyne source in synthetic transformations under mild, sustainable conditions.

Technology Process of Ethynyl p-tolyl sulfone

There total 22 articles about Ethynyl p-tolyl sulfone 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: 99.0%

trimethylsilyl p-tolylsulfonylacetylene (34452-56-7) → ethynyl p-tolyl sulfone (13894-21-8)

Guidance literature:

With sodium fluoride; In methanol; water; at 10 ℃; for 0.25h;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1997::AID-EJOC1997>3.0.CO;2-A

Reference yield: 88.0%

(E)-1-(phenylseleno)-1-(trimethylsilyl)-2-(p-tolylsulfonyl)ethene (86409-87-2) → diphenyl diselenide (1666-13-3) + ethynyl p-tolyl sulfone (13894-21-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 3h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00166a030

Reference yield: 87.0%

ethynylphenyl-iodonium-1,1,1-trifluoromethanesulfonate (125803-61-4) + sodium 4-methylbenzenesulfinate (824-79-3) → ethynyl p-tolyl sulfone (13894-21-8)

Guidance literature:

In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.1021/jo00071a037

upstream raw materials:

1-ethynylsulfanyl-4-methyl-benzene

4-(toluene-4-sulfonyl)-isoxazol-5-ylamine

trimethylsilyl p-tolylsulfonylacetylene

ethynylphenyl-iodonium-1,1,1-trifluoromethanesulfonate

Downstream raw materials:

(E)-1--2-tosylethylene

1-Methyl-4-[(E)-2-(2-methyl-cyclohex-2-enyl)-ethenesulfonyl]-benzene

1-Methyl-4-[(E)-2-(2-methylene-cyclohexyl)-ethenesulfonyl]-benzene

7-methoxycarbonyl-2-p-toluenesulfonyl-7-azanorbornadiene

Refernces

Redox-Activated Amines in C(sp³)-C(sp) and C(sp³)-C(sp²) Bond Formation Enabled by Metal-Free Photoredox Catalysis

10.1021/acscatal.8b03437

The research presented in an academic article in the American Chemical Society journal ACS Catalysis focused on the development of a metal-free, photoredox catalytic strategy to form C(sp3)-C(sp) and C(sp3)-C(sp2) bonds using redox-activated primary amine derivatives. The study explored the reaction between 2,4,6-triphenylpyridinium salts and alkynyl-p-toluenesulfones to synthesize functionalized alkynes. The experiments, conducted under green LED light, involved the use of Eosin Y as a photocatalyst, DIPEA as a sacrificial reductant, and a MeOH/DCE mixture as a solvent system. The reaction conditions were optimized and the scope of the reaction was investigated using a variety of substrates, including secondary alkyl, primary benzyl, and allyl-bound primary amines as well as complex drug molecules. The study also included mechanistic studies to understand the reactivity differences between primary and secondary alkyl-substituted pyridinium salts, using techniques such as fluorescence quenching, cyclic voltammetry, and kinetic studies in conjunction with relevant chemical reactions and analytical experiments to validate the effectiveness of their strategy.