PHENYL 2-(TRIMETHYLSILYLETHYNYL) SULFONE

Base Information

• Chemical Name: PHENYL 2-(TRIMETHYLSILYLETHYNYL) SULFONE
• CAS No.: 32501-93-2
• Molecular Formula: C11H14O2SSi
• Molecular Weight: 238.382
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID90400434
• Nikkaji Number: J308.285G
• Wikidata: Q82203416
• Mol file: 32501-93-2.mol

Synonyms:1-benzenesulfonyl-2-trimethylsilylacetylene;1-benzenesulphonyl-2-trimethylsilylacetylene;phenylsulfonylethynyltrimethylsilane;phenyl trimethylsilylethynyl sulfone;

Chemical Property of PHENYL 2-(TRIMETHYLSILYLETHYNYL) SULFONE

Chemical Property:

• Vapor Pressure: 0.000828mmHg at 25°C
• Melting Point: 65-66 °C
• Boiling Point: 315.1oC at 760 mmHg
• Flash Point: 144.3oC
• PSA: 42.52000
• Density: 1.102g/cm3
• LogP: 5.99560
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 238.04837739
• Heavy Atom Count: 15
• Complexity: 366

Purity/Quality:

1-PHENYLSULFONYL-2-(TRIMETHYLSILYL)ACETYLENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C[Si](C)(C)C#CS(=O)(=O)C1=CC=CC=C1

Technology Process of PHENYL 2-(TRIMETHYLSILYLETHYNYL) SULFONE

There total 5 articles about PHENYL 2-(TRIMETHYLSILYLETHYNYL) 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: 81.0%

phenylthioethynyl trimethylsilane (63139-23-1) → 1-(Phenylsulfonyl)-2-(trimethylsilyl)acetylene (32501-93-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/chem.201903392

Reference yield: 75.0%

benzenesulfonyl chloride (98-09-9) + Bis(trimethylsilyl)ethyne (14630-40-1) → 1-(Phenylsulfonyl)-2-(trimethylsilyl)acetylene (32501-93-2)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1016/0022-328X(85)87362-9

Reference yield:

diphenyldisulfane (882-33-7) → 1-(Phenylsulfonyl)-2-(trimethylsilyl)acetylene (32501-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 °C

2.1: 3-chloroperoxybenzoic acid / CH₂Cl₂

With n-butyllithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ol060608y

upstream raw materials:

benzenesulfonyl chloride

Bis(trimethylsilyl)ethyne

phenylthioethynyl trimethylsilane

diphenyldisulfane

Downstream raw materials:

3,5-Dinitro-benzoic acid (1S,2S)-2-methyl-3-oxo-2-vinyl-cyclopentyl ester

3,5-Dinitro-benzoic acid (1R,2S)-2-methyl-3-oxo-2-vinyl-cyclopentyl ester

2-methyl-2-<(Z)-2-(phenylsulfonyl)vinyl>-1,3-cyclopentanedione

4-(benzenesulfonyl)-3-(trimethylsilyl)phenol

Refernces

• 1、 Chandanshive, Jay Zumbar,Bonini, Bianca Flavia,Gentili, Denis,Fochi, Mariafrancesca,Bernardi, Luca,Franchini, Mauro Comes. "Regiocontrolled synthesis of ring-fused thieno[2,3-c]pyrazoles through 1,3-dipolar cycloaddition of nitrile imines with sulfur-based acetylenes". experimental part. p. 6440 - 6447. Retrieved 2011/01/13.
• 2、 Chen,Trudell. "A simplified method for the preparation of ethynyl P-tolyl sulfone and ethynyl phenyl sulfone". . p. 3149 - 3155. Retrieved 2007/10/02.