92614-55-6

Basic information

• Product Name: O-TOLYL-METHANESULFONYL CHLORIDE
• Synonyms: 2-(Methylphenyl)methylsulphonyl chloride;2-Methylbenzylsulphonyl chloride;N-o-Tolyl-malonamicacidethylester;(2-Methylphenyl)methanesulfonyl chloride ,97%;2-Methylbenzylsulphonyl chloride 97%;(2-methylphenyl)methanesulfonyl chloride(SALTDATA: FREE);BenzeneMethanesulfonylchloride, 2-Methyl-;2-Methylbenzylsulphonylchloride97%
• CAS NO: 92614-55-6
• Molecular Formula: C₈H₉ClO₂S
• Molecular Weight: 204.67
• Mol File: 92614-55-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 52 °C
• Boiling Point: 307.9 °C at 760 mmHg
• Flash Point: 140 °C
• Appearance: /
• Density: 1.325 g/cm³
• Vapor Pressure: 0.00128mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: O-TOLYL-METHANESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: O-TOLYL-METHANESULFONYL CHLORIDE(92614-55-6)
• EPA Substance Registry System: O-TOLYL-METHANESULFONYL CHLORIDE(92614-55-6)

Safety Data

• Hazard Codes: C,Xn
• Statements: 22
• Hazardous Substances Data: 92614-55-6(Hazardous Substances Data)

Usage

General Description

O-TOLYL-METHANESULFONYL CHLORIDE, also known as OTMSC, is a chemical compound that belongs to the family of organic sulfones. It is commonly used as a reagent in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. OTMSC is a versatile and widely used building block in the synthesis of various compounds. It is a highly reactive compound and is often used as a source of sulfonyl groups in chemical reactions. OTMSC is a colorless to light yellow liquid with a pungent odor, and it should be handled with caution due to its corrosive and toxic nature.

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

Upstream product

• 73338-92-8 S-(2-methylbenzyl)isothiouronium chloride 
• 552-45-4 1-chloromethyl-2-methylbenzene 

Downstream Products

• 864135-47-7 4-bromo-3-tert-butoxycarbonylmetoxy-5-[3-(1-o-tolylmethanesulfonylpiperidin-4-ylamino)phenyl]thiophene-2-carboxylic acid methyl ester 
• 1417156-35-4 1-(2-methylphenyl)-3-phenyl-2-thia-3-azabicyclo[3.1.0]hexane 2,2-dioxide 
• 1417156-21-8 N-allyl-1-(2-methylphenyl)-N-phenylmethanesulfonamide 
• 950257-33-7 1-(2-methylphenyl)-N-phenylmethanesulfonamide 
• 112941-34-1 1-(2-methylphenyl)methanesulfonamide 

Relevant articles and documents

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.

Palladium-Catalyzed Remote meta-Selective C-H Bond Silylation and Germanylation

Selective meta-C-H activation of arenes to date has met with a limited number of functionalizations. Expanding the horizon of meta-C-H functionalization, herein we disclose an unprecedented meta-silylation and -germanylation protocol by employing a simple nitrile-based directing template. Longer linkers between the target site and the directing template were successfully explored for meta-silylation (sp2-? and sp2-ζ). Additionally, synthetic utility was demonstrated with several postsynthetic elaborations and with a formal synthesis of TAC101, a promising drug for the treatment of lung cancer.