4-Chlorothiophenol - ≥98% , CAS No.106-54-7

CAS: 106-54-7 Cat. No.: C101766 Molecular Weight: 144.62 Beilstein Registry Number: 605971 EC Number: 203-408-9

GRADE & PURITY ≥98%

Synonyms

4-chlorothio phenol | 4-chloro thiophenol | EN300-18299 | AI3-18024 | Benzenethiol, 4-chloro- | p-Chlorophenylmercaptan | VZXOZSQDJJNBRC-UHFFFAOYSA- | p-Chlorothiophenol | p-chloro-thiophenol | ?4-Chloro thiophenol | 1O71UA6O72 | Z57834219 | p-Chlorthiofe

Storage

Room temperature,Argon charged

Shipped In

FedEx DG Service

Overview

4-Chlorothiophenol undergoes oxidative coupling catalyzed by iron(III)-tetra phenyl prophyrin to form disulfides.
4-Chlorothiophenol was used to modify poly(vinyl chloride) and to synthesize poly(vinyl chloride) with halogen groups. Reactant involved in: . Oxidation to disulfides using cobalt-salen catalysts and air oxidizing agents . Thiourea-catalyzed sulfa-Michael addition to acryloyloxazolidinones . Pummerer-type cyclization . C-H Activation and C-S cross-coupling with heterocycles . Allylic sulfenylation with allylic carbonates . Lewis acid-catalyzed electrophilic ring-opening reactions of 2-aryl-3,4-dihydropyrans

Specifications

Synonyms

4-chlorothio phenol | 4-chloro thiophenol | EN300-18299 | AI3-18024 | Benzenethiol, 4-chloro- | p-Chlorophenylmercaptan | VZXOZSQDJJNBRC-UHFFFAOYSA- | p-Chlorothiophenol | p-chloro-thiophenol | ?4-Chloro thiophenol | 1O71UA6O72 | Z57834219 | p-Chlorthiofe

Specifications & Purity

≥98%

Storage

Room temperature, Argon charged

Shipped In

FedEx DG Service

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 528760490
• Canonical Smiles: C1=CC(=CC=C1S)Cl
• IUPAC Name: 4-chlorobenzenethiol
• InChIKey: VZXOZSQDJJNBRC-UHFFFAOYSA-N
• INCHI: 1S/C6H5ClS/c7-5-1-3-6(8)4-2-5/h1-4,8H
• Isomeric SMILES: C1=CC(=CC=C1S)Cl
• WGK Germany: 3
• RTECS: DC1050000
• UN Number: 3261
• Molecular Weight: 144.62
• Beilstein: 605971
• Reaxy-Rn: 605971
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=605971&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Thiophenols

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Thiophenols
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Thiophenols
• Alternative Parents: Chlorobenzenes Aryl chlorides Thiols Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Thiophenol - Halobenzene - Chlorobenzene - Monocyclic benzene moiety - Aryl halide - Aryl chloride - Arylthiol - Hydrocarbon derivative - Organosulfur compound - Organochloride - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as thiophenols. These are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TPMT Tchem Thiopurine S-methyltransferase (45 Activities)

Discover Target: TPMT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

LLTC cell line (101 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Insoluble in water, soluble in hot alcohols, ethers, and benzene.
• Sensitivity: Air sensitive.
• Flash Point(°F): 109°C
• Flash Point(°C): 109°C
• Boil Point(°C): 205-207°C
• Melt Point(°C): 49-51°C
• Molecular Weight: 144.620 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 143.98 Da
• Monoisotopic Mass: 143.98 Da
• Topological Polar Surface Area: 1.000 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 66.900
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Karuppasamy Kohila Rani, Qiong Yang, Yuan-Hui Xiao, Rajkumar Devasenathipathy, Zhihao Lu, Xinya Chen, Lu Jiang, Zemin Li, Qinghua Liu, Haonan Chen, Liuyingzi Yu, Zhuoyao Li, Soukaina Khayour, Junjie Wang, Kaili Wang, Gongqiang Li, De-Yin Wu, Gang Lu.  (2023)  Boosting the Plasmon-Mediated Electrochemical Oxidation of p-Aminothiophenol with p-Hydroxythiophenol as Molecular Cocatalyst.  ACS Applied Materials & Interfaces,      [PMID:38038343] [10.1021/acsami.3c12778]

2. Ying-Hua Zhou, Chen-Chen Jiang, Zhou Yu, Ya-Hao Wang, Ju-Fang Zheng, Xiao-Shun Zhou.  (2023)  In situ Raman monitoring of electroreductive dehalogenation of aryl halides at an Ag/aqueous solution interface.  Analytical Methods,  15  (6): (771-777).  [PMID:36683583] [10.1039/D2AY02060B]

3. Ming-Hui Sun, Ming-Yu Qi, Zi-Rong Tang, Yi-Jun Xu.  (2022)  Dual cocatalysts decorated CdS nanoparticles for efficient dehydrocoupling of thiols into disulfides.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2022.122019]

4. Chen-Chen Jiang, Xiao-Chong Li, Jian-Ang Fan, Jia-Ying Fu, Xu-Nan Huang-Fu, Jia-Jie Li, Ju-Fang Zheng, Xiao-Shun Zhou, Ya-Hao Wang.  (2022)  Electrochemically activated carbon–halogen bond cleavage and C–C coupling monitored by in situ shell-isolated nanoparticle-enhanced Raman spectroscopy.  ANALYST,  147  (7): (1341-1347).  [PMID:35244130] [10.1039/D2AN00054G]

5. Hai-Bo Wang, Bei-Bei Tao, An-Li Mao, Zhong-Liang Xiao, Yan-Ming Liu.  (2021)  Self-assembled copper nanoclusters structure-dependent fluorescent enhancement for sensitive determination of tetracyclines by the restriction intramolecular motion.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2021.130729]

6. Xuejing Chen, Zhiyuan Shen, Yonghong He, Tian Guan, Qinghua He, Bei Wang, Luyuan Xie, Guangxia Feng, Bangrong Lu, Xuesi Zhou, Jiafan Liu, Zhigang Fan.  (2019)  Dual-wavelength digital holographic phase and fluorescence microscopy combining with Raman spectroscopy for micro-quartz pieces-based dual-channel encoded suspension array.  OPTICS EXPRESS,  27  (3): (1894-1910).  [PMID:30732236] [10.1364/OE.27.001894]

7. Renxuan Liu, Tao Sha, Qiuhong Zhou, Bei Nie.  (2018)  Copper-surrogated galvanic displacement of silver dendrite imprinted on flexible and transparent silk fibroin membrane as a SERS-active substrate and sub-dividable catalyst.  APPLIED SURFACE SCIENCE,      [PMID:] [10.1016/j.apsusc.2018.11.223]

8. Yi Zhang, Chen Chen, Ya-Long Zhang, Ling-Yi Kong, Jian-Guang Luo.  (2018)  Target discovery of cytotoxic withanolides from Physalis angulata var. villosa via reactivity-based screening.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:29367159] [10.1016/j.jpba.2017.12.047]

9. Xu Dong, Ruimin Li, Christian G. Schäfer, Fang Wang.  (2017)  Composite MF@Ag-NPs microspheres for label-free quantitative detection of uric acid.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2017.03.042]

10. Yating Li, Xiaolong Zhang, Gaohong He, Fengxiang Zhang.  (2016)  Sulfonated poly(phenylene sulfide) grafted polysulfone proton exchange membrane with improved stability.  INTERNATIONAL JOURNAL OF HYDROGEN ENERGY,      [PMID:] [10.1016/j.ijhydene.2016.09.183]

11. Ruimin Li, Yuting Zhang, Jing Tan, Jiaxun Wan, Jia Guo, Changchun Wang.  (2016)  Dual-Mode Encoded Magnetic Composite Microsphere Based on Fluorescence Reporters and Raman Probes as Covert Tag for Anticounterfeiting Applications.  ACS Applied Materials & Interfaces,      [PMID:27010437] [10.1021/acsami.6b02359]

12. Li-Jun You, Qiao An, Jia Guo, Jack J. Hu, Chang-Chun Wang.  (2013)  Uniform MF/Ag-NPs core–shell composite microspheres as isolated SERS substrates for quick and sensitive detection of insecticide.  RSC Advances,  3  (38): (17469-17476).  [PMID:] [10.1039/C3RA42260G]

13. Yong Liu, Peiyi Wu.  (2013)  Meditating Metal Coenhanced Fluorescence and SERS Around Gold Nanoaggregates in Nanosphere as Bifunctional Biosensor for Multiple DNA Targets.  ACS Applied Materials & Interfaces,      [PMID:23734937] [10.1021/am401468a]

14. Hao Hao, Meng Liu, Ge Tang, Yi Liu, Feng-Lei Jiang.  (2024)  CdSe/ZnS Quantum Dots with Enhanced Stability and Conductivity by Thiolphenyl Ligands for Displays.  ACS Applied Nano Materials,      [PMID:] [10.1021/acsanm.4c01133]

15. Chen Zeng, Jianxiong Chen, Chengbiao Zhu, Zhenwei Wei.  (2025)  Highly sensitive and rapid screening of radical electrochemical intermediates by chemical labeling untargeted mass spectrometry.  TALANTA,      [PMID:40020611] [10.1016/j.talanta.2025.127791]

16. Ge Tang, Xiao-Hang He, Meng Liu, Hao Hao, Yi Liu, Feng-Lei Jiang.  (2024)  Insights into the Fluorescence Quenching of CdSeS Quantum Dots by Thiophenol Ligands.  Journal of Physical Chemistry C,      [PMID:] [10.1021/acs.jpcc.4c01302]

17. Yunjia Wei, Dexiang Chen, Xingce Fan, Xiao Tang, Lei Yao, Xing Zhao, Qiang Li, Jiawei Wang, Teng Qiu, Qi Hao.  (2024)  Unveiling Plasmon-Induced Suzuki–Miyaura Reactions on Silver Nanoparticles via Raman Spectroscopy.  ACS Catalysis,      [PMID:] [10.1021/acscatal.4c04578]

18. Gu Yuqing, He Chang, Zhang Yuqing, Lin Li, Thackray Benjamin David, Ye Jian.  (2020)  Gap-enhanced Raman tags for physically unclonable anticounterfeiting labels.  Nature Communications,  11  (1): (1-13).  [PMID:31980613] [10.1038/s41467-019-14070-9]