51419-59-1

Basic information

• Product Name: 4-Methylbenzylsulfonyl chloride
• Synonyms: (4-Methylphenyl)methanesulfonyl chloride, 4-Methylbenzenemethanesulfonyl chloride, p-Methyl-α-toluenesulfonyl chloride, p-Tolylmethanesulfonyl chloride;^a-p-Xylenesulfonyl chloride, 97%;alpha-p-Xylenesulfonyl chloride, 97%;(4-Methylphenyl)methanesulfonyl chloride, TECH;4-Methylbenzylsulfon;BenzeneMethanesulfonylchloride, 4-Methyl-;4-Methylbenzylsulfonyl chloride 96%;P-TOLYL-METHANESULFONYL CHLORIDE
• CAS NO: 51419-59-1
• Molecular Formula: C₈H₉ClO₂S
• Molecular Weight: 204.67
• Product Categories: Fluorobenzene;Phenyls & Phenyl-Het;Sulphonyl Chlorides;Phenyls & Phenyl-Het;Sulphonyl Chlorides
• Mol File: 51419-59-1.mol
• Article Data: 27

Chemical Properties

• Melting Point: 76-80 °C
• Boiling Point: 305.2 °C at 760 mmHg
• Flash Point: 138.4 °C
• Appearance: /
• Density: 1.325 g/cm³
• Vapor Pressure: 0.0015mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 4-Methylbenzylsulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylbenzylsulfonyl chloride(51419-59-1)
• EPA Substance Registry System: 4-Methylbenzylsulfonyl chloride(51419-59-1)

Safety Data

• Hazard Codes: C,Xi
• Statements: 22-34
• Safety Statements: 26-28-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 51419-59-1(Hazardous Substances Data)

Usage

Description

4-Methylbenzylsulfonyl chloride, also known as p-Toluenesulfonyl chloride, is an organic compound with the chemical formula C7H7ClO2S. It is a colorless to pale yellow liquid with a pungent odor and is commonly used as a reagent in organic synthesis.

Uses

Used in Pharmaceutical Industry:
4-Methylbenzylsulfonyl chloride is used as a synthetic reagent for the production of (R)-1-alkyl-substituted tetrahydro-β-carbolines, which are important intermediates in the synthesis of various pharmaceutical compounds. These compounds have potential applications in the development of new drugs targeting various diseases and conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-Methylbenzylsulfonyl chloride is used as a protecting group for amines and alcohols during organic reactions. Its use as a protecting group helps prevent unwanted side reactions and allows for selective functionalization of specific groups in a molecule, which is crucial for the synthesis of complex organic compounds.
Used in Research and Development:
4-Methylbenzylsulfonyl chloride is also utilized in research and development for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatility as a reagent makes it a valuable tool for chemists working on the design and synthesis of novel molecules with potential applications in various industries.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 4553, 1984 DOI: 10.1016/S0040-4039(01)81491-X

InChI:InChI=1/C8H9ClO2S/c1-7-2-4-8(5-3-7)6-12(9,10)11/h2-5H,6H2,1H3

Upstream product

• 104-81-4 4-Methylbenzyl bromide 
• 4498-99-1 4-methylbenzylthiol 
• 28868-76-0 2-chlorodimethylmalonate 
• 104-82-5 4-Methylbenzyl chloride 
• 940-63-6 amino[(4-methylbenzyl)thio]methaniminium chloride 

Downstream Products

• 104-82-5 4-Methylbenzyl chloride 
• 1588-49-4 4,4'-dimethylstilbene 
• 51392-39-3 (α-Chlor-4-methylbenzyl)(4-methylbenzyl)sulfon 
• 950232-83-4 C₁₅H₁₇NO₂S 

Relevant articles and documents

Preparation method of novel abscisic acid agonist AM1

The invention discloses a preparation method of a novel abscisic acid agonist AM1, and relates to chemical synthesis. The preparation method comprises the following steps: taking cheap quinoline as a raw material, and preparing a key intermediate 1-propyl

Alkyne Linchpin Strategy for Drug:Pharmacophore Conjugation: Experimental and Computational Realization of a Meta-Selective Inverse Sonogashira Coupling

The late-stage functionalization (LSF) of pharmaceutical and agrochemical compounds by the site-selective activation of C-H bonds provides access to diverse structural analogs and expands synthetically-accessible chemical space. We report a C-H functionalization LSF strategy that hinges on the use of an alkyne linchpin to assemble conjugates of sp2-rich marketed pharmaceuticals and agrochemicals with sp3-rich 3D fragments and natural products. This is accomplished through a template-assisted inverse Sonogashira reaction that displays high levels of selectivity for the meta position. This protocol is also amenable to distal structural modifications of α-amino acids. The transformation of alkyne functionality to other functional groups further highlights the applicative potential. Computational and experimental mechanistic studies shed light on the detailed mechanism. Turnover-limiting 1,2-migratory insertion of the bromoalkyne coupling partner occurs after relatively fast C-H activation. While this insertion occurs unselectively, regioconvergence results from one of the adducts undergoing a 1,2-trialkylsilyl migration to form the alkynylated product. A heterobimetallic Pd-Ag transition structure is essential for product formation in the β-bromide elimination step.

Design, synthesis and evaluation of sulfonylurea-containing 4-phenoxyquinolines as highly selective c-Met kinase inhibitors

Deregulation of receptor tyrosine kinase c-Met has been reported in human cancers and is considered as an attractive target for small molecule drug discovery. In this study, a series of 4-phenoxyquinoline derivatives bearing sulfonylurea moiety were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against tested four cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant potency as compared with foretinib, with the most promising compound 13x (c-Met kinase IC50 = 1.98 nM) demonstrated relatively good selectivity versus 10 other tyrosine kinases and remarkable cytotoxicities against HT460, MKN-45, HT-29 and MDA-MB-231 with IC50 values of 0.055 μM, 0.064 μM, 0.16 μM and 0.49 μM, respectively. The preliminary structure activity relationships indicated that a sulfonylurea moiety as linker as well as mono-EGWs (such as R1 = 4-F) on the terminal phenyl rings contributed to the antitumor activity.