Dibenzyl disulfide

Base Information

• Chemical Name: Dibenzyl disulfide
• CAS No.: 150-60-7
• Deprecated CAS: 325737-14-2
• Molecular Formula: C14H14S2
• Molecular Weight: 246.397
• Hs Code.: 29309090
• European Community (EC) Number: 205-764-0,695-033-6
• NSC Number: 677465,6841
• UNII: BG7680605N
• DSSTox Substance ID: DTXSID6059738
• Nikkaji Number: J60.275B
• Wikidata: Q27140119
• Metabolomics Workbench ID: 45255
• ChEMBL ID: CHEMBL121047
• Mol file: 150-60-7.mol

Synonyms:bis(phenylmethyl) disulfide

Chemical Property of Dibenzyl disulfide

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 2.91E-05mmHg at 25°C
• Melting Point: 69-72 °C(lit.)
• Refractive Index: 1.643
• Boiling Point: 367.3 °C at 760 mmHg
• Flash Point: 217.2 °C
• PSA: 50.60000
• Density: 1.168 g/cm³
• LogP: 4.76820
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 246.05369279
• Heavy Atom Count: 16
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

DibenzylDisulphide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 22-36/37-37-24

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C1=CC=C(C=C1)CSSCC2=CC=CC=C2
• Uses: Dibenzyl disulfide has been used in lubricating oil formulations to improve thermal and aging resistance of the oil. It is used an antioxidant in rubber compounding, stabilizer for petroleum fractions, additive to silicone oils. The soly in oils is increased by the presence of benzyl alcohol.

Technology Process of Dibenzyl disulfide

There total 416 articles about Dibenzyl disulfide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

dibenzylamine (103-49-1) → dibenzyl disulphide (150-60-7) + dibenzyl sulfide (538-74-9) + dibenzyltrisulfide (6493-73-8) + N-benzyl-benzenecarbothioamide (14309-89-8) + phenylmethanethiol (100-53-8)

Guidance literature:

With sulfur; at 170 ℃; for 0.25h; Microwave irradiation; neat (no solvent);

DOI:10.1080/17415993.2011.640329

Reference yield: 67.0%

benzyl chloride (100-44-7) → dibenzyl disulphide (150-60-7) + phenylmethanethiol (100-53-8)

Guidance literature:

With piperidinium thiotungstate; In N,N-dimethyl-formamide; at 25 ℃; for 1h; Product distribution; Mechanism; other alkyl mono- and dihalides; other piperidinium tetrathiometalate;

DOI:10.1021/jo00274a002

Reference yield: 55.6%

1-Phenylethanol (98-85-1,13323-81-4) + phenylmethanethiol (100-53-8) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + dibenzyl disulphide (150-60-7)

Guidance literature:

In toluene; at 60 ℃; for 0.5h;

DOI:10.3762/bjoc.12.259

upstream raw materials:

pyridine

benzyl thiocyanate

acetic acid

phenylmethanethiol

Downstream raw materials:

benzyl-(3,3,3-trichloro-ξ-propenyl)-sulfide

phenylmethanethiol

benzaldehyde

dithiobenzoic acid

Refernces

• 1、 Quintanilla, Ma. Gloria,Guerra, Eva,Dotor, Jessica,Maresova, Jirina,Barba, Fructuoso,Martin, Avelino. "Synthesis and characterization of benzylidene bis-dithiobenzoate". . p. 1691 - 1699. Retrieved 2005.
• 2、 Magnus Ph.,Ladlow,Elliott. "Models for a hypothetical mechanism of action of the anticancer agent vinblastine". . p. 7929 - 7930. Retrieved 1987.
• 3、 Zolfigol, Mohammad Ali. "A convenient method for production of thionitrites and disulfides under mild and heterogeneous condition". . p. 1593 - 1597. Retrieved 2000.
• 4、 Fu, Chunling,Huang, Xian,Ma, Shengming. "Convenient stereoselective synthesis of 3-hydroxy-2-iodo-2(E)-alkenyl sulfides via iodohydroxylation of 1,2-allenyl sulfoxides in the presence of BnSH". . p. 6063 - 6065. Retrieved 2004.
• 5、 Schreiber,Fernandez. "-". . p. 2478. Retrieved 1961.
• 6、 Price,Jaques. "". . p. 1140. Retrieved 1914.
• 7、 Maiti, Debabrata,Woertink, Julia S.,Vance, Michael A.,Milligan, Ashley E.,Narducci Sarjeant, Amy A.,Solomon, Edward I.,Karlin, Kenneth D.. "Copper(I)/S8 reversible reactions leading to an end-on bound dicopper(II) disulfide complex: Nucleophilic reactivity and analogies to copper-dioxygen chemistry". . p. 8882 - 8892. Retrieved 2007.
• 8、 Kato,Mitsunobu. "-". . p. 4227. Retrieved 1970.
• 9、 Li, Jian,Cai, Zhong-Jian,Wang, Shun-Yi,Ji, Shun-Jun. "A tetra-: N -butylammonium iodide mediated reaction of indoles with Bunte salts: Efficient 3-sulfenylation of indoles under metal-free and oxidant-free conditions". . p. 9384 - 9387. Retrieved 2016.
• 10、 Ross et al.. "". . p. 4853,4856. Retrieved 1961.