Bis(4-chlorophenyl) disulfide

Base Information

• Chemical Name: Bis(4-chlorophenyl) disulfide
• CAS No.: 1142-19-4
• Deprecated CAS: 1089712-52-6
• Molecular Formula: C12H8Cl2S2
• Molecular Weight: 287.234
• Hs Code.: 29309090
• European Community (EC) Number: 214-531-2
• NSC Number: 677444,32025
• UNII: NMT539C7LN
• DSSTox Substance ID: DTXSID7061562
• Nikkaji Number: J7.277J
• Wikidata: Q27284959
• ChEMBL ID: CHEMBL121019
• Mol file: 1142-19-4.mol

Synonyms:1142-19-4;4,4'-Dichlorodiphenyl disulfide;Bis(4-chlorophenyl) disulfide;Disulfide, bis(4-chlorophenyl);Di(p-chlorophenyl) disulfide;DDDS (pesticide);DDDS;Disulfide, bis(p-chlorophenyl);p-Chlorophenyl disulfide;4-Chlorophenyl disulfide;1,2-bis(4-chlorophenyl)disulfane;1-Chloro-4-[(4-chlorophenyl)disulfanyl]benzene;Bis(p-chlorophenyl) disulfide;p,p'-Dichlorodiphenyl disulfide;BIS(4-CHLOROPHENYL)DISULFIDE;Bis(4-chlorophenyl) disulphide;BIS(P-CHLOROPHENYL)DISULFIDE;NSC 32025;NSC-32025;C12H8Cl2S2;NSC 677444;HSDB 2791;EINECS 214-531-2;UNII-NMT539C7LN;NMT539C7LN;AI3-16362;CHEMBL121019;NSC32025;NSC677444;NSC-677444;1,1'-disulfanediylbis(4-chlorobenzene);Disulfide, bis[4-chlorophenyl];Bis(4-chlorophenyl)disulphide;di(4-chlorophenyl)disulfide;bis(p-chlorophenyl)disulphide;bis(p-chlorophenyl)-disulfide;di(4-chlorophenyl) disulfide;SCHEMBL162332;4,4'-Dichlorophenyl disulfide;Bis(4-chlorophenyl) persulfide;bis-(4-chloro-phenyl)disulfide;DTXSID7061562;ZIXXRXGPBFMPFD-UHFFFAOYSA-;C12-H8-Cl2-S2;1,2-Bis(4-chlorophenyl);disulfane;BDBM50555857;MFCD00013642;NSC823871;STK820839;Bis(4-chlorophenyl) disulfide, 97%;AKOS001092350;CS-W013999;NSC-823871;BIS-(4-CHLOROBENZENE)-DISULFIDE;4,4\'-DICHLORODIPHENYL DISULFIDE;AC-16467;AS-60151;LS-63039;D0360;FT-0633399;1-chloro-4-(4-chlorophenyl)disulfanylbenzene;4,4'-DICHLORODIPHENYL DISULFIDE [HSDB];1-Chloro-4-[(4-chlorophenyl)disulfanyl]benzene #;J-513993;Q27284959;Z57056361

Chemical Property of Bis(4-chlorophenyl) disulfide

Chemical Property:

• Appearance/Colour: Colorless or light yellow liquid
• Melting Point: 71-74 °C(lit.)
• Boiling Point: 373.174 °C at 760 mmHg
• Flash Point: 167.843 °C
• PSA: 50.60000
• Density: 1.431 g/cm³
• LogP: 5.79280
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Methanol
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 285.9444480
• Heavy Atom Count: 16
• Complexity: 175

Purity/Quality:

98.00% ^*data from raw suppliers

Di(p-chlorophenyl)Disulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C1=CC(=CC=C1SSC2=CC=C(C=C2)Cl)Cl
• Uses: Bis(4-chlorophenyl) disulfide may be used to synthesize non-symmetrical heterodimer 4-chlorophenyl-2′-nitrophenyl disulfide.

Technology Process of Bis(4-chlorophenyl) disulfide

There total 227 articles about Bis(4-chlorophenyl) 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: 79.0%

p-Chlorothiophenol (106-54-7) + para-nitrobenzenethiol (1849-36-1) → 4,4'-dichlorodiphenyl disulfide (1142-19-4) + di(p-nitrophenyl) disulfide (100-32-3) + 1-(4-chlorophenyl)-2-(4-nitrophenyl)disulfane (20168-75-6)

Guidance literature:

p-Chlorothiophenol; para-nitrobenzenethiol; With dmap; water; In ethanol; at 20 ℃; for 0.0833333h;

With iodine; In ethanol; at 70 ℃; for 3h; Sealed tube;

DOI:10.1002/asia.201900620

Reference yield: 76.0%

thiophenol (108-98-5) + p-Chlorothiophenol (106-54-7) → 4,4'-dichlorodiphenyl disulfide (1142-19-4) + 1-(4-chlorophenyl)-2-phenyldisulfane (33965-85-4) + diphenyldisulfane (882-33-7)

Guidance literature:

thiophenol; p-Chlorothiophenol; With dmap; water; In ethanol; at 20 ℃; for 0.0833333h;

With iodine; In ethanol; at 70 ℃; for 3h; Sealed tube;

DOI:10.1002/asia.201900620

Reference yield: 65.0%

4-nitro-4’-chlorodiphenylsulfoxide (24535-53-3) → 4,4'-dichlorodiphenyl disulfide (1142-19-4) + di(p-nitrophenyl) disulfide (100-32-3) + p-chlorobenzenesulphinamide (16096-86-9)

Guidance literature:

With sulfur; ammonia; at 20 ℃; for 6h;

DOI:10.1246/cl.1983.535

upstream raw materials:

pyridine

4-chlorophenyl thiocyanate

acetic acid

N,N-dimethyl-aniline

Downstream raw materials:

bis-benzenesulfonyl-(4-chloro-phenylsulfanyl)-methane

p-chlorophenyl p-chlorobenzenethiosulfinate

p-chlorobenzenesulfonic anhydride

dimethyl-(4-chlorophenyl)sulfonium triiodide

Refernces

• 1、 Nakamura, Michiaki,Ito, Osami,Matsuda, Minoru. "Substituent Effect on the Rate Constants for the Reactions between Benzenethiyl Radicals and Stable Free Radicals Estimated by Flash Photolysis". . p. 698 - 701. Retrieved 1980.
• 2、 Movassagh,Lakouraj,Ghodrati. "Caro's acid supported on silica gel. Part 1: Oxidative coupling of thiols to disulfides". . p. 3597 - 3603. Retrieved 1999.
• 3、 Shirini,Lakouraj,Mohammadpour-Baltork,Asadi. "Polymer supported reagents: Oxidative selection between thiols". . p. 1833 - 1837. Retrieved 2003.
• 4、 Tajik,Shirini,Farahkah,Lakouraj,Baltork. "Coupling of thiols catalyzed by trinitratocerium(IV) bromate". . p. 1384 - 1385. Retrieved 2002.
• 5、 Chung, Moo-Il,D'Souza, Valerian T.,Szmant, H. Harry. "Thiol-Olefin Cooxidation (TOCO) Reaction. 10. Phenyl Allyl Ether and p-Chlorothiophenol". . p. 1741 - 1744. Retrieved 1987.
• 6、 Lenard?o, Eder J.,Lara, Renata G.,Silva, Márcio S.,Jacob, Raquel G.,Perin, Gelson. "Clean and fast oxidative transformation of thiols to disulfides under solvent-free conditions". . p. 7668 - 7670. Retrieved 2007.
• 7、 Silveira, Claudio C.,Mendes, Samuel R.. "Catalytic oxidation of thiols to disulfides using iodine and CeCl3·7H2O in graphite". . p. 7469 - 7471. Retrieved 2007.
• 8、 Kabir, S. M. Humayun,Langler, Richard F.. "Benzoyloxymethyl p-toluenethiosulfonate: A crystalline, stable synthetic equivalent for+CH2S+". . p. 362 - 367. Retrieved 2005.
• 9、 Sanders, Brian C.,Hassan, Sayed M.,Harrop, Todd C.. "NO2- activation and reduction to no by a nonheme Fe(NO2)2 complex". . p. 10230 - 10233. Retrieved 2014.
• 10、 Schmid,G.H.,Csizmadia,V.M.. "-". . p. 1338 - 1341. Retrieved 1966.