557-22-2

Basic information

• Product Name: 1,2-dithiolane
• Synonyms: 1,2-Dithiolane; Dithiolane
• CAS NO: 557-22-2
• Molecular Formula: C₃H₆S₂
• Molecular Weight: 106.2097
• Mol File: 557-22-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 150.5°C at 760 mmHg
• Flash Point: 84.7°C
• Density: 1.211g/cm³
• Vapor Pressure: 4.88mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 1,2-dithiolane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dithiolane(557-22-2)
• EPA Substance Registry System: 1,2-dithiolane(557-22-2)

Safety Data

• Hazardous Substances Data: 557-22-2(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic organic compound

Structure

Five-membered ring with two sulfur atoms

Physical state

Colorless liquid

Odor

Strong

Uses

a. Solvent
b. Intermediate for synthesis of pharmaceuticals, pesticides, and other organic compounds
c. Metal-catalyzed reactions
d. Chelating agent in analytical chemistry

Potential applications

a. Antifungal agents
b. Antibacterial agents

Safety concerns

a. Flammability
b. Toxicity if ingested or inhaled

Handling precautions

Careful handling required due to flammability and toxicity

Upstream product

• 180-96-1 1,5-dithiaspiro[5.5]undecane 
• 6331-22-2 2-methyl-2-phenyl-[1,3]dithiane 
• 54844-67-6 2-decyl-<1,3>-dithiane 
• 74327-18-7 2-Hexyl-2-propyl-1,3-dithiane 
• 57009-70-8 2-(3,4,5-trimethoxyphenyl)-1,3-dithiane 
• 108378-67-2 2-(3,4-dihydroxyphenyl)-1,3-propylenedithioacetal 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 69278-13-3 2-(4-methoxyphenyl)-1,3-dithiane 1-oxide 
• 96-35-5 glycolic acid methyl ester 
• 28915-80-2 2,3,4-tri-O-acetyl-L-rhamnopyranose 
• 109-70-6 1.3-chlorobromopropane 
• 39854-45-0 1,3-dithiane of cholestanone 
• 74327-19-8 ethyl 2-octyl-1,3-dithiane-2-carboxylate 

Downstream Products

• 3866-79-3 1,3-bis(p-toluenesulfonylthio)propane 
• 109-80-8 1.3-propanedithiol 
• 505-20-4 1,2-dithiane 

Relevant articles and documents

Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

Depigmenting keratin materials utilizing dithiolane compounds

A cosmetic regime or regimen for depigmenting, lightening and/or bleaching keratin materials, especially the skin, entails topically applying thereon a cosmetic composition containing a dithiolane compound of formula (I): in which: Y is O, NR1 or SR1 is a hydrogen atom; a C1-C20 alkyl radical or an optionally substituted phenyl radical;R is a hydrogen atom; or a C1-C20 alkyl radical, or an optionally substituted phenyl radical, or a C1-C8 alkyl radical containing an optionally substituted phenyl substituent;n=0 or 1 or 2; and also the salts, chelates, solvates and optical isomers thereof.

A new approach to the reduction of sulfoxides to sulfides with 1,3-dithiane in the presence of electrophilic bromine as catalyst

A new, mild, and novel method is described for the efficient deoxygenation of sulfoxides to their corresponding sulfides with 1,3-dithiane at room temperature in the presence of catalytic amounts of N-bromosuccinimide (NBS), 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO), or Br2 as the source of electrophilic bromine.