538-74-9

Basic information

• Product Name: Dibenzyl sulphide
• Synonyms: BENZYLSULFID;BENZYL SULFIDE;DIBENZYL SULFIDE;DIBENZYL SULPHIDE;Benzene, 1,1'-[thiobis(methylene)]bis-;BENZYLSULPHIDE;dibenzylsulfane;Thiobis(methylene)bis(benzene)
• CAS NO: 538-74-9
• Molecular Formula: C₁₄H₁₄S
• Molecular Weight: 214.33
• EINECS: 208-703-6
• Product Categories: sulfide Flavor
• Mol File: 538-74-9.mol
• Article Data: 225

Chemical Properties

• Melting Point: 44-47 °C(lit.)
• Boiling Point: 131 °C / 2mmHg
• Flash Point: >110°C
• Appearance: White/Crystals
• Density: 1.0880
• Vapor Pressure: 0.000516mmHg at 25°C
• Refractive Index: 1.6170 (estimate)
• Storage Temp.: 0-10°C
• Water Solubility: <0.1 g/100 mL at 21℃
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,1145
• BRN: 1911157
• CAS DataBase Reference: Dibenzyl sulphide(CAS DataBase Reference)
• NIST Chemistry Reference: Dibenzyl sulphide(538-74-9)
• EPA Substance Registry System: Dibenzyl sulphide(538-74-9)

Safety Data

• Safety Statements: 22-24/25
• RIDADR: UN 3335
• WGK Germany: 2
• RTECS: DC0512500
• F: 13
• TSCA: Yes
• Hazardous Substances Data: 538-74-9(Hazardous Substances Data)

Usage

Chemical Properties

beige crystals or powder with an unpleasant smell

Uses

Organic synthesis.

Synthesis Reference(s)

Canadian Journal of Chemistry, 53, p. 1480, 1975 DOI: 10.1139/v75-205Tetrahedron Letters, 27, p. 1073, 1986 DOI: 10.1016/S0040-4039(86)80051-X

General Description

Colorless plates or pale beige crystalline solid with a crippling stench .

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Organosulfides, such as Dibenzyl sulphide, are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.

Fire Hazard

Dibenzyl sulphide is combustible.

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors ofSOx.

Purification Methods

Crystallise the sulfide from EtOH/water (10:1), or repeatedly from Et2O. It has also been purified by chromatography on Al2O3 (pentane as eluent), then recrystallised from EtOH [Kice & Bowers J Am Chem Soc 84 2390 1962]. Dry it in a vacuum at 30o over P2O5, fused under nitrogen and re-dried. [Beilstein 6 IV 2649.]

InChI:InChI=1/C14H14S/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H2

Upstream product

• 56-23-5 tetrachloromethane 
• 56554-80-4 1-chloro-heptadec-8-ene 
• 67-66-3 chloroform 
• 16601-40-4 S-benzyl phenyl-methanethiosulfonate 
• 15719-64-9 methylammonium carbonate 
• 108-24-7 acetic anhydride 
• 100-44-7 benzyl chloride 
• 100-53-8 phenylmethanethiol 
• 150-60-7 dibenzyl disulphide 
• 122-52-1 triethyl phosphite 
• 1939-99-7 benzenesulfonyl chloride 
• 5418-20-2 benzaldehyde dibenzyldithioacetal 
• 31247-20-8 α,α'-dibromodibenzyl sulfide 
• 100-39-0 benzyl bromide 

Downstream Products

• 621-08-9 Dibenzyl sulfoxide 
• 620-32-6 dibenzyl sulfone 
• 58881-56-4 2,2'-thiobis[1-(4-bromophenyl)ethanone] 
• 78-95-5 chloroacetone 
• 102477-96-3 (α-Benzoyloxy-benzyl)-benzyl-sulfid 
• 54397-50-1 C₁₈H₂₀N₂O₄S 
• 84354-99-4 1-(Benzylsulfanyl-phenyl-methyl)-4-phenyl-[1,2,4]triazolidine-3,5-dione 
• 21529-87-3 S,S-dibenzul-S-ethylsulfonium tetrafluoroborate 
• 591-50-4 iodobenzene 
• 120188-76-3 C₁₅H₁₇OS⁽¹⁺⁾*C₇H₇O₃S^(1-) 
• 76447-87-5 S,S-dibenzyl-N-(ethoxycarbonyl)sulfilimine 
• 3249-66-9 S,S-dibenzyl-N-(toluene-4-sulfonyl)-sulfimide 
• 150-60-7 dibenzyl disulphide 

Relevant articles and documents

Heterogeneously Ni-Pd nanoparticle-catalyzed base-free formal C-S bond metathesis of thiols

This study rationally designed a heterogeneously catalyzed system (i.e., using Ni-Pd alloy nanoparticles supported on hydroxyapatite (Ni-Pd/HAP) under an H2atmosphere) achieving an efficient base-free formal C-S bond metathesis of various thiolsviasuppression of the Ni catalysis deactivation.

N-bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides

An efficient reduction of sulfoxides to sulfides mediated by N-bromosuccinimide (NBS)/HCl system has been developed. This protocol shows good functional group compatibility as well as broad substrates scope with operational simplicity.

One-Pot Synthesis of Thiocarbamates

An efficient isocyanide-based synthesis of S-thiocarbamates was discovered and thoroughly investigated. The new reaction protocol is a one-pot procedure and allows the direct conversion of N-formamides into thiocarbamates by initial dehydration with p-toluene sulfonyl chloride to the respective isocyanide and subsequent addition of a sulfoxide component. Contrary to recent literature, which also uses isocyanides as starting material, but with other sulfur reagents than sulfoxides, in this protocol, no isolation and purification of the isocyanide component is necessary, thus significantly decreasing the environmental impact and increasing the efficiency of the synthesis. The new protocol was applied to synthesize a library of sixteen thiocarbamates, applying four N-formamides and four commercially available sulfoxides. Furthermore, experiments were conducted to investigate the reaction mechanism. Finally, four norbornene-based thiocarbamate monomers were prepared and applied in controlled ring-opening metathesis polymerization (ROMP) reactions. The polymers were characterized by size-exclusion chromatography (SEC) and their properties were investigated utilizing differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).