Production Method 1

882-33-7

931-59-9

Reaction Conditions

1.1 Reagents: Hydrochloric acid ,  Sodium hypochlorite Solvents: Dichloromethane ;  30 min, 0 °C; 30 min, 0 °C

Reference

Safe and practical ex-situ chlorination of electronically diverse π-systems

Aguilar, Glen C.; Lis, Patrycja A. ; Wise, Dan E. ; Martinez, Jenny S.; Parasram, Marvin, Tetrahedron Letters, 2023, 124,

Production Method 2

931-59-9

Reaction Conditions

1.1 Reagents: Chlorosuccinimide Solvents: Dichloromethane ;  0 °C; 15 min, 0 °C

Reference

Bifunctional Polyene Cyclizations: Synthetic Studies on Pimarane Natural Products

Feilner, Julian M. ; Plangger, Immanuel ; Wurst, Klaus; Magauer, Thomas, Chemistry - A European Journal, 2021, 27(48), 12410-12421

Production Method 3

931-59-9

Reaction Conditions

1.1 Reagents: Chlorine Solvents: Pentane ;  1 h, rt

Reference

The Endocyclic Restriction Test: The Geometries of Nucleophilic Substitutions at Sulfur(VI) and Sulfur(II)

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter, Journal of Organic Chemistry, 2008, 73(24), 9627-9632

Production Method 4

931-59-9

Reaction Conditions

1.1 Reagents: Chlorine

Reference

Electrophilic additions to strained alkenes. II. The reaction of benzeneselenenyl chloride with tricyclo[4.2.2.02,5]deca-3,7-diene derivatives

Garratt, Dennis G.; Ryan, M. Dominic; Kabo, Ann, Canadian Journal of Chemistry, 1980, 58(22), 2329-39

Production Method 5

882-33-7

931-59-9

Reaction Conditions

1.1 Reagents: Iodobenzene dichloride Solvents: Dichloromethane ;  20 min, rt

Reference

Method for synthesizing aryl sulfenyl/selenenyl chloride

, China, , ,

Production Method 6

931-59-9

Reaction Conditions

1.1 Reagents: Sulfuryl chloride Solvents: Dichloromethane ;  0 °C; 1 h, 0 °C

Reference

Synthesis and biological evaluation of nonsymmetrical aromatic disulfides as novel inhibitors of acetohydroxyacid synthase

Li, Zai-Shun; Wang, Wei-Min; Lu, Wei; Niu, Cong-Wei; Li, Yong-Hong; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(13), 3723-3727

Production Method 7

931-59-9

Reaction Conditions

1.1 Reagents: Sulfuryl chloride Solvents: Dichloromethane ;  0 °C; 1 h, 0 °C

Reference

Synthesis, Crystal Structure, in Vitro Acetohydroxyacid Synthase Inhibition, in Vivo Herbicidal Activity, and 3D-QSAR of New Asymmetric Aryl Disulfides

Shang, Jun; Wang, Wei-Min; Li, Yong-Hong; Song, Hai-Bin; Li, Zheng-Ming; et al, Journal of Agricultural and Food Chemistry, 2012, 60(34), 8286-8293

Production Method 8

882-33-7

931-59-9

Reaction Conditions

1.1 Reagents: Chlorine

Reference

Studies of aromatic disulfides. VII. Synthesis of asymmetric aromatic and aliphatic-aromatic disulfides

Stepanov, B. I.; Rodionov, V. Ya.; Chibisova, T. A.; Yagodina, L. A.; Stankevich, A. D., Zhurnal Organicheskoi Khimii, 1977, 13(2), 370-4

Production Method 9

882-33-7

931-59-9

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Benzene ;  15 min, 0 °C
1.2 Reagents: Sulfuryl chloride Solvents: Dichloromethane ;  0 °C

Reference

Synthesis and deployment of an elusive fluorovinyl cation equivalent: Access to quaternary α-(1'-fluoro)vinyl amino acids as potential PLP enzyme inactivators

McCune, Christopher D.; Beio, Matthew L.; Sturdivant, Jill M.; de la Salud-Bea, Roberto; Darnell, Brendan M.; et al, Journal of the American Chemical Society, 2017, 139(40), 14077-14089

Production Method 10

882-33-7

931-59-9

Reaction Conditions

1.1 Reagents: Chlorine Solvents: Carbon tetrachloride ;  3 h, < 20 °C; 2 - 4 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Preparation and characterization of o- or p-phenylthio substituted phenol compounds

Feng, Baicheng; Yu, Fanuan; Li, Peipei, Qingdao Keji Daxue Xuebao, 2010, 31(3), 231-233

Production Method 11

882-33-7

931-59-9

Reaction Conditions

1.1 Reagents: Chlorine Solvents: Carbon tetrachloride ;  3 h, < 20 °C; 2 h, < 20 °C

Reference

Method for preparation of substituted diphenyl sulfide via Friedel-Crafts reaction

, China, , ,

Production Method 12

931-59-9

Reaction Conditions

1.1 Reagents: Sulfuryl chloride

Reference

Benzenesulfenyl chloride

Zelcans, Gunars; Hutton, Thomas K.; Rios, Ramon; Shibata, Norio, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2013, 1, 1-14

Production Method 13

62167-00-4

931-59-9

Reaction Conditions

1.1 Reagents: Sulfuryl chloride Solvents: Dichloromethane

Reference

Synthesis of [1c-13C]-Labelled Gangliosides GM3 and NMR-Spectroscopic Investigations in Cell Cultures

Gretzke, Dirk, 1998, , ,

Production Method 14

931-59-9

Reaction Conditions

Reference

Concerning the mechanism of the formation of phosphoranes from the reaction of tricoordinated phosphorus compounds and alkyl benzenesulfenates

Denney, Donald B.; Denney, Dorothy Z.; Gavrilovic, Dragan M., Phosphorus and Sulfur and the Related Elements, 1981, 11(1), 1-9

Production Method 15

931-59-9

Reaction Conditions

1.1 Reagents: Chlorosuccinimide Solvents: Dichloromethane ;  0 °C; 15 min, 0 °C

Reference

Palladium-Catalyzed Regio- and Stereoselective Chlorothiolation of Terminal Alkynes with Sulfenyl Chlorides

Iwasaki, Masayuki; Fujii, Tomoya; Yamamoto, Arisa; Nakajima, Kiyohiko; Nishihara, Yasushi, Chemistry - An Asian Journal, 2014, 9(1), 58-62

Production Method 16

931-59-9

Reaction Conditions

1.1 Reagents: Sulfuryl chloride Solvents: Dichloromethane ;  cooled; 1 h, cooled

Reference

Triazole-asymmetric disulfide compounds as herbicides and their preparation, agrochemical compositions and use in the control of weeds

, China, , ,

Production Method 17

931-59-9

Reaction Conditions

1.1 Reagents: Sulfuryl chloride Solvents: Dichloromethane ;  0 °C; 1 h, 0 °C

Reference

Preparation of heterocyclic ring-containing asymmetric aromatic sulfide compound as AHAS inhibitors useful as herbicides

, China, , ,

Production Method 18

931-59-9

Reaction Conditions

1.1 Reagents: Chlorosuccinimide Solvents: Dichloromethane ;  0 °C; 15 min, 0 °C

Reference

In Situ Activation of Disulfides for Multicomponent Reactions with Isocyanides and a Broad Range of Nucleophiles

Lei, Xiaofang; Wang, Yuanyuan; Fan, Erkang; Sun, Zhihua, Organic Letters, 2019, 21(5), 1484-1487

Production Method 19

931-59-9

Reaction Conditions

1.1 Reagents: Chlorine

Reference

Cyclofunctionalization of 2-allylphenols with sulfur chlorides. III. 2-(Arylthiomethyl)-2,3-dihydrofuro[3,2-h]quinolines from 7-allyl- and 7-methallyl-8-hydroxyquinoline, respectively, and arylsulfenyl chlorides

Meinhold, H.; Muehlstaedt, M.; Muslih, R. M., Journal fuer Praktische Chemie (Leipzig), 1989, 331(1), 136-40

Production Method 20

931-59-9

Reaction Conditions

1.1 Reagents: Sulfuryl chloride Solvents: Pentane ;  0.5 h, 0 °C; 0 °C → rt; 1 h, rt

Reference

Catalytic Thia-Sommelet-Hauser Rearrangement: Application to the Synthesis of Oxindoles

Li, Yuye; Shi, Yi; Huang, Zhong-Xing; Wu, Xin-Hu; Xu, Peng-Fei; et al, Organic Letters, 2011, 13(5), 1210-1213

Phenylsulfenyl Chloride Raw materials

• Benzeneethanethioic acid
• Phenyl disulfide

Phenylsulfenyl Chloride Preparation Products

• Phenylsulfenyl Chloride (931-59-9)

• 1. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 2. Evolution of important glucosinolates in three common Brassica vegetables during their processing into vegetable powder and in vitro gastric digestion
  Nan Fu,Naphaporn Chiewchan,Xiao Dong Chen Food Funct., 2020,11, 211-220
• 3. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 4. Excellent kinetics of single-phase Gd-doped ceria fuel electrodes in solid oxide cells?
  Andreas Nenning,Manuel Holzmann,Jürgen Fleig,Alexander K. Opitz Mater. Adv., 2021,2, 5422-5431
• 5. Excellent lithium ion storage property of porous MnCo2O4 nanorods?
  Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen Fang RSC Adv., 2016,6, 23074-23084

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzene and substituted derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives

Recent Advances in the Application of Phenylsulfenyl Chloride (CAS: 931-59-9) in Chemical Biology and Pharmaceutical Research

Phenylsulfenyl chloride (CAS: 931-59-9) is a versatile sulfur-containing reagent that has garnered significant attention in recent years due to its unique reactivity and broad applicability in chemical biology and pharmaceutical research. This compound, characterized by the presence of a sulfenyl chloride functional group (-SCl) attached to a phenyl ring, serves as a key intermediate in the synthesis of various sulfur-containing compounds, including sulfides, sulfoxides, and sulfones. Its ability to participate in selective sulfurization reactions makes it particularly valuable for the modification of biomolecules and the development of novel therapeutic agents.

Recent studies have highlighted the role of phenylsulfenyl chloride in the site-specific modification of proteins and peptides. For instance, researchers have utilized this reagent to introduce thioether linkages into peptide backbones, enabling the stabilization of secondary structures and the enhancement of proteolytic resistance. Such modifications are critical for the development of peptide-based therapeutics, where stability and bioavailability are often limiting factors. Additionally, phenylsulfenyl chloride has been employed in the synthesis of sulfenamide derivatives, which exhibit promising biological activities, including antimicrobial and anticancer properties.

In the context of drug discovery, phenylsulfenyl chloride has been instrumental in the construction of sulfur-containing heterocycles, a class of compounds that are well-represented in FDA-approved drugs. Recent work has demonstrated its utility in the synthesis of benzothiazoles and thiazolidinones, scaffolds that are frequently encountered in antimicrobial, anti-inflammatory, and antitumor agents. The reagent's ability to facilitate the formation of carbon-sulfur bonds under mild conditions has made it a preferred choice for medicinal chemists seeking to diversify their compound libraries.

Beyond its applications in synthetic chemistry, phenylsulfenyl chloride has also found use in chemical biology as a tool for studying redox processes. Sulfenylation, the covalent modification of cysteine residues by sulfenyl chloride, is a post-translational modification that plays a crucial role in cellular signaling and oxidative stress responses. Researchers have developed probes based on phenylsulfenyl chloride to detect and quantify protein sulfenylation in live cells, providing insights into the dynamics of redox regulation. These tools have been particularly valuable in the study of diseases associated with oxidative stress, such as neurodegenerative disorders and cancer.

Despite its utility, the handling of phenylsulfenyl chloride requires careful consideration due to its reactivity and potential toxicity. Recent advancements in reagent stabilization and delivery systems have addressed some of these challenges, enabling safer and more efficient use in laboratory settings. For example, the development of polymer-supported phenylsulfenyl chloride reagents has reduced the risks associated with handling the free compound while maintaining its reactivity. Such innovations are expected to further expand the applications of this reagent in both academic and industrial research.

In conclusion, phenylsulfenyl chloride (CAS: 931-59-9) continues to be a valuable tool in chemical biology and pharmaceutical research, with recent studies underscoring its versatility and potential for innovation. Its applications span from the synthesis of bioactive compounds to the study of cellular redox processes, making it a reagent of choice for researchers in these fields. As new methodologies for its use emerge, phenylsulfenyl chloride is poised to play an even greater role in advancing our understanding of sulfur chemistry and its implications for drug discovery and development.

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