Methyl-p-toluenesulfonate - AR, ≥98% , CAS No.80-48-8

CAS: 80-48-8 Cat. No.: M105177 Molecular Weight: 186.23 Beilstein Registry Number: 609209 EC Number: 201-283-5

GRADE & PURITY AR, ≥98%

Synonyms

methyl-4-methylbenzenesulfonate | MFCD00069406 | NSC406335 | NSC-406335 | p-Methylbenzenesulfonate methyl ester | AKOS008938769 | METHYL P-METHYLBENZENESULFONATE | Tox21_303790 | EINECS 201-283-5 | METHYL 4-TOLUENE SULFONATE [HSDB] | p-Toluolsulfonsaeure

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Methyl p-toluenesulfonate is sulfonate ester present as potentially genotoxic impurity in drug substances. Kinetics of reactions of methyl p-toluenesulfonate with N,N-dimethylaniline has been investigated. It participates in selective 1-substitution reaction of tetrazole.

Specifications

Synonyms

methyl-4-methylbenzenesulfonate | MFCD00069406 | NSC406335 | NSC-406335 | p-Methylbenzenesulfonate methyl ester | AKOS008938769 | METHYL P-METHYLBENZENESULFONATE | Tox21_303790 | EINECS 201-283-5 | METHYL 4-TOLUENE SULFONATE [HSDB] | p-Toluolsulfonsaeure

Specifications & Purity

AR, ≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

AR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=CC=C(C=C1)S(=O)(=O)OC
• IUPAC Name: methyl 4-methylbenzenesulfonate
• InChIKey: VUQUOGPMUUJORT-UHFFFAOYSA-N
• INCHI: 1S/C8H10O3S/c1-7-3-5-8(6-4-7)12(9,10)11-2/h3-6H,1-2H3
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC
• WGK Germany: 3
• RTECS: XT7000000
• UN Number: 3261
• Molecular Weight: 186.23
• Beilstein: 609209
• Reaxy-Rn: 609209
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=609209&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzenesulfonic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzenesulfonic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzenesulfonate esters
• Alternative Parents: p-Methylbenzenesulfonates Tosyl compounds Benzenesulfonyl compounds Arylsulfonic acids and derivatives Organosulfonic acid esters Sulfonyls Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzenesulfonate ester - P-methylbenzenesulfonate - Tosyl compound - Arylsulfonic acid or derivatives - Benzenesulfonyl group - Toluene - Organosulfonic acid ester - Sulfonyl - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Organic oxide - Organosulfur compound - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzenesulfonate esters. These are arenesulfonate esters that result from the formal condensation of the hydroxy group of an alcohol, enol, phenol or heteroarenol with benzenesulfonic acid.
• 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)

PHPT1 Tbio 14 kDa phosphohistidine phosphatase (0 Activities)

Discover Target: PHPT1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ether, alcohol, benzene and chloroform. Slightly soluble in petroleum ether. Insoluble in water.
• Sensitivity: Moisture sensitive
• Freezing Point(°C): 25 °C
• Refractive Index: 1.5162-1.5182
• Flash Point(°F): 305°F
• Flash Point(°C): 152 °C
• Boil Point(°C): 292°C
• Melt Point(°C): 24-30°C
• Molecular Weight: 186.230 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 186.035 Da
• Monoisotopic Mass: 186.035 Da
• Topological Polar Surface Area: 51.800 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 219.000
• 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. Zizhao Qian, Yanglei Zheng, Qing Li, Lujie Wang, Feiya Fu, Xiangdong Liu.  (2021)  Amidation Way of Diphenolic Acid for Preparing Biopolybenzoxazine Resin with Outstanding Thermal Performance.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.1c00554]

2. Faming Wang, Pengfei Ren, Katrien V. Bernaerts, Yifu Fu, Wanjun Hu, Naizhen Zhou, Tianzhu Zhang.  (2020)  Thermoresponsive Poly(2-propyl-2-oxazoline) Surfaces of Glass for Nonenzymatic Cell Harvesting.  ACS Applied Bio Materials,      [PMID:35021716] [10.1021/acsabm.0c00650]

3. Zhongxiang Zhao, Yongjian Lou, Zenghui Dai, Feiya Fu, Xiangdong Liu.  (2018)  Biobased Composites Prepared Using an Environmentally Friendly Water-Slurry Methodology.  INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH,      [PMID:] [10.1021/acs.iecr.8b00960]

4. Yang Zhao, Yazhen Xu, Qingbo Xu, Feiya Fu, Yanyan Zhang, Takeshi Endo, Xiangdong Liu.  (2018)  Significant Improvement on Polybenzoxazine Toughness Achieved by Amine/Benzoxazine Copolymerization-Induced Phase Separation.  MACROMOLECULAR CHEMISTRY AND PHYSICS,  219  (6): (1700517).  [PMID:] [10.1002/macp.201700517]

5. Hongqiang Yan, Nannan Li, Jie Cheng, Pingan Song, Zhengping Fang, Hao Wang.  (2017)  Fabrication of flame retardant benzoxazine semi-biocomposites reinforced by ramie fabrics with bio-based flame retardant coating.  POLYMER COMPOSITES,      [PMID:] [10.1002/pc.24617]

6. Wen Zhou, Fucheng Zhu, Yuanlin Li, Chen Liu, Jie Xu, Houmei Liu.  (2025)  Developing a solid-phase extraction method based on a novel polymer-silica composite for analysis of sulfonate genotoxic impurities in drugs.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.113182]

7. Chengcheng Zhao, Jian Qin, Dingyu Zhang, Xue Li, Ning Yang, Tingyu Gao, Junliang Song, Yule Song, Shouzhen Huang, Huan Xu.  (2025)  NGR-poly(2-ethyl-2-oxazoline)-cholesteryl methyl carbonate enhances the antitumor effect of quercetin liposomes in triple-negative breast cancer.  PHARMACEUTICAL DEVELOPMENT AND TECHNOLOGY,      [PMID:39764693] [10.1080/10837450.2025.2450434]

8. Pan Deng, Lin Chen, Zi-Jie Cao, Yue Li, Guan-Qi Zheng, Yu-Zhong Wang, Xiu-Li Wang.  (2025)  Bioinspired Dual-Stimulus-Responsive Macromolecular Engineering Enables Chemically Recyclable, High-Performance and Fire-Retardant Plastic.  MACROMOLECULES,      [PMID:] [10.1021/acs.macromol.5c00753]

9. Haoran Sun, Junyi Jiang, Yanglei Zheng, Shuangfei Xiang, Shujun Zhao, Feiya Fu, Xiangdong Liu.  (2023)  Synthesis of a renewable bisguaiacol amide and its hydrogen bonding effect on enhancing polybenzoxazine performance.  Polymer Chemistry,  14  (14): (1613-1621).  [PMID:] [10.1039/D2PY01424F]

10. Luqiao Wen, Shouzhen Huang, Weiang Du, Caili Zhu, Huan Xu.  (2020)  Effects of the molecular weight and molar ratio of poly(2-ethyl-2-oxazoline)-based lipid on the pH sensitivity, stability, and antitumor efficacy of liposomes.  DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY,      [PMID:31944130] [10.1080/03639045.2020.1717514]