Benzenesulfenyl chloride

Base Information

• Chemical Name: Benzenesulfenyl chloride
• CAS No.: 931-59-9
• Molecular Formula: C6H5ClS
• Molecular Weight: 144.625
• Hs Code.: 2930909090
• European Community (EC) Number: 632-987-4
• DSSTox Substance ID: DTXSID60451599
• Nikkaji Number: J28.456D
• Wikidata: Q72445090
• Mol file: 931-59-9.mol

Synonyms:benzenesulfenyl chloride;Phenylsulfenylchloride;931-59-9;phenyl thiohypochlorite;phenylsulfenyl chloride;(PHENYLSULFANYL)CHLORANE;Phenylthio chloride;phenyl sulfenyl chloride;benzene sulfenyl chloride;SCHEMBL397524;DTXSID60451599;thiohypochlorous acid phenyl ester;JWUKZUIGOJBEPC-UHFFFAOYSA-N;A844462;J-523958

Chemical Property of Benzenesulfenyl chloride

Chemical Property:

• Appearance/Colour: wine hygroscopic oily liquid
• Melting Point: 44 °C
• Boiling Point: 261.7 °C at 760 mmHg
• Flash Point: 110.3 °C
• PSA: 25.30000
• Density: 1.25 g/cm³
• LogP: 2.93250
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 143.9800490
• Heavy Atom Count: 8
• Complexity: 59.5

Purity/Quality:

98%,99%, ^*data from raw suppliers

PhenylsulfenylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SCl
• Uses: Phenylsulfenyl Chloride is an intermediate used in the synthesis of Tabanone (T003450), which is found in oils of Trifolium pratense L. and is a potential natural anti-oxidant.

Technology Process of Benzenesulfenyl chloride

There total 31 articles about Benzenesulfenyl chloride 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: 95.5%

o-nitrobenzenesulfenanilide (4837-33-6) + 4-methyl-benzoyl chloride (874-60-2) → 4-methyl-N-phenylbenzamide (6833-18-7) + benzenesulfenyl chloride (931-59-9)

Guidance literature:

With Allyl ether; triphenylphosphine; In 1,4-dioxane; at 18 - 20 ℃; for 5h;

Reference yield: 95.0%

acetyl chloride (75-36-5) + menthyl sulfenate → benzenesulfenyl chloride (931-59-9) + 2-isopropyl-5-methylcyclohexyl acetate (89-48-5,2230-87-7,2552-91-2,2623-23-6,5157-89-1,16409-45-3,20777-36-0,20777-45-1,29066-34-0,42241-42-9,50539-17-8,55058-46-3,79199-84-1,146502-80-9)

Guidance literature:

at 0 ℃;

DOI:10.1016/0040-4039(95)02241-4

Reference yield: 93.0%

N-phenyl-benzenesulphenamide (14933-91-6) + benzoyl chloride (98-88-4) → N-phenyl benzoyl amide (93-98-1,5705-51-1) + benzenesulfenyl chloride (931-59-9)

Guidance literature:

With Allyl ether; triethylphosphine; In 1,4-dioxane; at 18 - 20 ℃; for 5h;

upstream raw materials:

N-chloro-succinimide

thiophenol

benzenenesulfenyl dimethylamine

dichloromethane

Downstream raw materials:

3,5-dimethyl-4-phenylsulfanyl-pyrrole-2-carboxylic acid ethyl ester

benzenesulfenic acid p-anisidide

diphenyl sulfide

4-bromophenyl phenyl disulfide

Refernces

• 1、 Ishii, Yutaro,Ito, Satoshi,Saito, Yuki,Uno, Daiki,Oba, Toru. "Synthesis of [2,3]naphthoporphyrins using 4,9-dihydro-4,9-ethano-2H-benz[f]isoindole as a benz[f]isoindole equivalent". . p. 8892 - 8898. Retrieved 2015.
• 2、 Ruostesuo, P.,Haekkinen, A.-M,Liias-Lepistoee, R.,Salminen, U.. "NMR chemical shifts and coupling constants of various nuclei of N,N-diethylbenzenesulfenamide, N,N-diethylbenzeneseleneamide and some related sulfur amides". . p. 1105 - 1108. Retrieved 1988.
• 3、 Ismailov, Ismail E.,Ivanov, Ivaylo K.,Christov, Valerij Ch.. "Trifunctionalized allenes. Part III. Electrophilic cyclization and cycloisomerization of 4-phosphorylated 5-hydroxypenta-2,3-dienoates: An expedient synthetic method to construct 2,5-dihydro-1,2-oxaphospholes, furan-2(5H)-ones and 2,5-dihydrofurans". . p. 314 - 323. Retrieved 2020.
• 4、 Nishiyama, Yoshitake,Yokoshima, Satoshi,Fukuyama, Tohru. "Total Synthesis of (-)-Cardiopetaline". . p. 2359 - 2362. Retrieved 2016.
• 5、 Jiao, Lei,Wang, Feng-Yuan. "Total Synthesis of (?)-Arborisidine". . p. 12732 - 12736. Retrieved 2021.
• 6、 Mueller,Butler. "-". . p. 1533,1534. Retrieved 1968.
• 7、 Du, Yunfei,Li, Xiaoxian,Li, Yadong,Sun, Fengxia,Yu, Zhenyang,Zhang, Dongke,Zhang, Jingran. "Intramolecular Chalcogenylation of Isooxazolines Mediated by PhICl 2and Diorganyl Disulfides or Diselenides". . . Retrieved 2021/10/05.