5616-55-7

Basic information

• Product Name: Benzaldehyde ethane-1,2-diyl dithioacetal
• Synonyms: 2-Phenyl-1,3-dithiolane;Benzaldehyde (ethane-1,2-diyl)dithioacetal;Benzaldehyde ethane-1,2-diyl dithioacetal
• CAS NO: 5616-55-7
• Molecular Formula: C₉H₁₀S₂
• Molecular Weight: 182.3057
• Mol File: 5616-55-7.mol
• Article Data: 120

Chemical Properties

• Melting Point: 68-70 °C
• Boiling Point: 307°Cat760mmHg
• Flash Point: 147.4°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 0.00135mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Benzaldehyde ethane-1,2-diyl dithioacetal(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde ethane-1,2-diyl dithioacetal(5616-55-7)
• EPA Substance Registry System: Benzaldehyde ethane-1,2-diyl dithioacetal(5616-55-7)

Safety Data

• Hazardous Substances Data: 5616-55-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 433, 1989 DOI: 10.1080/00397918908050683Tetrahedron Letters, 32, p. 2259, 1991 DOI: 10.1016/S0040-4039(00)79696-1

InChI:InChI=1/C9H10S2/c1-2-4-8(5-3-1)9-10-6-7-11-9/h1-5,9H,6-7H2

Upstream product

• 100-52-7 benzaldehyde 
• 540-63-6 ethane-1,2-dithiol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 2183-30-4 3-(1,3-dithiolan-2-ylidene)pentane-2,4-dione 
• 5721-88-0 2-phenyl-1,3-oxathiolane 
• 776-88-5 5,5-dimethyl-2-phenyl-[1,3]dioxane 
• 774-48-1 (diethoxymethyl)benzene 
• 5908-41-8 benzoyltrimethylsilane 
• 65-85-0 benzoic acid 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 6784-59-4 1-(1,3-dithiolan-2-ylidene)propan-2-one 
• 932-90-1 Benzaldoxime 
• 836684-88-9 2-(1,3-dithiolan-2-ylidene)-3-oxobutanamide 

Downstream Products

• 1196-58-3 (1-ethylpropyl)benzene 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 74-84-0 ethane 
• 4808-30-4 bis(tributyltin)sulfide 
• 108-88-3 toluene 
• 139-66-2 diphenyl sulfide 
• 949-00-8 phenyl dithiobenzoate 
• 100-52-7 benzaldehyde 
• 1822-73-7 phenylthioethylene 
• 420-12-2 thirane 
• 74-85-1 ethene 
• 108-98-5 thiophenol 
• 71-43-2 benzene 
• 36456-49-2 2-Phenyl-1,3-dithiolane 1,1,3,3-tetraoxide 

Relevant articles and documents

PhIO-Mediated oxidative dethioacetalization/dethioketalization under water-free conditions

Treatment of thioacetals and thioketals with iodosobenzene in anhydrous DCM conveniently afforded the corresponding carbonyl compounds in high yields under water-free conditions. The mechanistic studies indicate that this dethioacetalization/dethioketalization process does not need water and the oxygen of the carbonyl products comes from the hypervalent iodine reagent.

Mesoporous sBa-15 silica catalyst functionalized with phenylsulfonic acid groups (SbA-15-ph-So3h) as efficient nanocatalyst for chemoselective thioacetalization of carbonyl compounds

In this research a Nano acidic catalyst was prepared and its efficiency on thioacetalization of carbonyl compounds was examined. For this aim we used modified SBA-15 as support, which have been modified by phenolic and sulfonic acid. SBA-15 is a member of

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

Trimethylsilyldiazomethane (TMS-CHN2) reacts readily with hetaryl thioketones to give sterically crowded 2-trimethylsilyl- 4,4,5,5-tetrahetaryl-1,3-dithiolanes with complete regioselectivity at -75 °C as well as at rt. Thiofluorenone, a relatively stable and highly reactive aryl thioketone, yields upon treatment with TMS-CHN2at -60 °C the corresponding 1,3,4-thiadiazoline. This unstable cycloadduct undergoes decomposition at ca. -45 °C and the silylated thiocarbonyl S-methanide generated thereby is trapped with complete regioselectivity by aryl or hetaryl thioketones forming also sterically crowded 2-trimethylsilyl-1,3- dithiolanes. The obtained 1,3-dithiolanes, by treatment with an equimolar amount of TBAF in a one-pot procedure, are converted in high yields into hetaryl/aryl-substituted ethenes or dibenzofulvenes, respectively, via a cycloreversion reaction of the intermediate 1,3-dithiolane carbanion. The presented protocol offers a new, highly efficient approach to tetrasubstituted ethenes and dibenzofulvenes bearing aryl and/or hetaryl substituents.