89568-79-6

Basic information

• Product Name: 1,3-Dithiane, 2-(4-methylphenyl)-2-phenyl-
• CAS NO: 89568-79-6
• Molecular Formula: C17H18S2
• Molecular Weight: 286.462
• Mol File: 89568-79-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,3-Dithiane, 2-(4-methylphenyl)-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dithiane, 2-(4-methylphenyl)-2-phenyl-(89568-79-6)
• EPA Substance Registry System: 1,3-Dithiane, 2-(4-methylphenyl)-2-phenyl-(89568-79-6)

Safety Data

• Hazardous Substances Data: 89568-79-6(Hazardous Substances Data)

Upstream product

• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 106-38-7 para-bromotoluene 
• 109-80-8 1.3-propanedithiol 
• 134-84-9 4-Methylbenzophenone 

Downstream Products

• 92517-97-0 1-[(3-Butylsulfanyl-propylsulfanyl)-phenyl-methyl]-4-methyl-benzene 
• 109-80-8 1.3-propanedithiol 
• 134-84-9 4-Methylbenzophenone 
• 92517-93-6 1-[1-(3-Butylsulfanyl-propylsulfanyl)-1-phenyl-propyl]-4-methyl-benzene 
• 620-83-7 1-methyl-4-(phenylmethyl)benzene 

Relevant articles and documents

Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN

A mild process using a combination of TMSCl and NaI in acetonitrile is used to regenerate carbonyl compounds from a variety of dithiane and dithiolane derivatives. This easy to handle and inexpensive protocol is also efficient to deprotect oxygenated and mixed acetals as 1,3-dioxanes, 1,3-dioxolanes and 1,3-oxathianes quantitatively. As a possible extension of this method, it was also shown that nitrogenated substrates such as hydrazones, N-tosylhydrazones, and ketimines reacted well under these conditions to give the expected ketones in high yields. The methodology proposed herein is a good alternative to the existing methods since it does not use metals, oxidants, reducing agents, acidic or basic media, and keto-products were obtained in high to excellent yields.

Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions

A novel metal-free process allowing the reductive desulfurization of various benzylic dithioketals to afford diarylmethane and benzylester derivatives with good to excellent yields is reported. At room temperature, this mild reduction process requires only the use of TMSCl and NaI in CH2Cl2 and tolerates a large variety of functional groups. (Figure presented.).

Reversed-polarity synthesis of Diaryl Ketones through palladium-catalyzed direct Arylation of 2-Aryl-1,3-dithianes

An umpolung approach to the synthesis of diaryl ketones has been developed based on in situ generation of acyl anion equivalents and their catalytic arylation. This method entails the base-promoted, palladium-catalyzed direct C-H arylation of 2- aryl-1,3-dithianes with aryl bromides. Use of MNACHTUNGTRENUNG( SiMe3)2 (M=Li, Na) base results in reversible deprotonation of the weakly acidic dithiane. In the presence of a Pd(NiXantphos)-based catalyst and aryl bromide, cross-coupling of the metallated 2-aryl- 1,3-dithiane takes place under mild conditions (2 h at rt) with yields as high as 96%. The resulting 2,2- diaryl-1,3-dithianes were converted into diaryl ketones by either molecular iodine, N-bromo succinimide (NBS) or Selectfluor in the presence of water. The dithiane arylation/hydrolysis can be performed in a one-pot procedure to yield a variety of diaryl ketones in good to excellent yields. This method is suitable for rapid and large-scale synthesis of diaryl ketones. A one-pot preparation of anti-cholesterol drug fenofibrate (TriCor) has been achieved on 10.0 mmol scale in 86% yield.