101268-22-8

Basic information

• Product Name: 1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE
• Synonyms: 1-(4-TOLUENESULFONYL)-3,3-DIMETHYLBUTANE-2-ONE;1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTAN-2-ONE;1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE;1-(4-Toluenesulfonyl)-3,3-dimethylbutan-2-one
• CAS NO: 101268-22-8
• Molecular Formula: C₁₃H₁₈O₃S
• Molecular Weight: 254.35
• Mol File: 101268-22-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 114.5-115 °C(Solv: water (7732-18-5); methanol (67-56-1))
• Boiling Point: 399.4±42.0 °C(Predicted)
• Appearance: /
• Density: 1.119±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE(101268-22-8)
• EPA Substance Registry System: 1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE(101268-22-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 101268-22-8(Hazardous Substances Data)

Usage

Description

1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE, also known as TosMIC or Evans' Oxazolidinone, is an organic compound characterized by a toluene group attached to a sulphur atom and a butane-2-one group. It is a colorless liquid with a strong, pungent odor and exhibits strong electrophilic properties due to the presence of the toluene sulphonyl group.

Uses

Used in Pharmaceutical Industry:
1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE is used as a reagent in organic synthesis for the production of pharmaceuticals. Its strong electrophilic nature makes it a valuable component in the synthesis of various drug molecules.
Used in Agrochemical Industry:
In the agrochemical industry, 1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE is utilized as a reagent in the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Polymer Manufacturing:
1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE is employed as a reagent in the manufacturing of polymers, playing a crucial role in the production of various types of polymers with specific properties.
Used in Organic Synthesis:
1-(4-TOLUENESULPHONYL)-3,3-DIMETHYLBUTANE-2-ONE is used as an intermediate in organic synthesis for the production of other organic compounds, showcasing its versatility and importance in the synthesis of a wide range of chemical products.

Upstream product

• 30263-65-1 1,1-dibromo-3,3-dimethylbutan-2-one 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 5469-26-1 1-Bromopinacolon 
• 98-59-9 p-toluenesulfonyl chloride 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 4124-41-8 p-toluenesulfonylanhydride 
• 630-18-2 tert-butyl isocyanide 
• 1538-98-3 p-tosyldiazomethane 
• 630-19-3 pivalaldehyde 
• 17510-46-2 3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene 

Relevant articles and documents

Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones

A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the 'sulfonyl-azide-free' ('SAFE') protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.

Photoinduced rearrangement of vinyl tosylates to β-ketosulfones

We developed a photoinduced radical fragmentation and rearrangement of vinyl tosylates that enables efficient formation of β-ketosulfones. This process is based on the photoinitiated homolysis of vinyl tosylate to release a sulfinyl radical from the tosyl group and the subsequent addition of a sulfinyl radical to another vinyl tosylate to form the desired β-ketosulfones. This simple protocol features a broad scope with both aromatic and aliphatic substrates, convenient reagents and operating systems.

Synthesis, X-ray Structure and Reactions of (2-Oxoalkyl)triarylbismuthonium Salts

Treatment of triarylbismuth difluorides 1 with silyl enol ethers 2 in the presence of boron trifluoride-diethyl ether or trimethylsilyl trifluoromethanesulfonate (triflate) gave (2-oxoalkyl)triarylbismuthonium tetrafluoroborates 3 and triflates 4 in good yields.A similar reaction of the difluorides 1 with hexamethyldisiloxane in the presence of the latter acid reagent led to the formation of oxybis(triarylbismuth) ditriflates 5.X-Ray crystallographic analyses of compounds 3a, 4a and 5a showed that the first two onium salts have a distorted tetrahedral geometry and the last, a μ-oxo type compound, has a distorted trigonal bipyramidal geometry around the bismuth centre.The stability of these bismuthonium salts may reasonably be attributed to the intramolecular coordinative interaction between the bismuth and oxygen atoms and also low nucleophilicity of the counter ions employed.The bismuthonium salt 3f readily underwent onium exchange with the phosphine 6 and the sulfide 9 to afford the corresponding phosphonium and sulfonium salts 7 and 10.The salts 3 and 4 also underwent coupling with a variety of nucleophiles such as the enolate 11, piperidine 13, the phenoxides 15, the thiolates 17, the sulfinate 19 and the halides 21 to afford the corresponding α-substituted ketones 12, 14, 16, 18, 20 and 22 in moderate to good yields, together with a good recovery of triphenylbismuthine 8.