773-64-8

Basic information

• Product Name: 2-Mesitylenesulfonyl chloride
• Synonyms: 2,4,6-TRIMETHYLBENZYLSULFONYL CHLORIDE;2,4,6-TRIMETHYLBENZENESULFONYL CHLORIDE;2-MESITYLENESULFONYL CHLORIDE;2-MESITYLENSULFONYL CHLORIDE;MESITYLENE-2-SULFONYL CHLORIDE;MESITYLENE-2-SULFONIC ACID CHLORIDE;MESITYLENESULFONYL CHLORIDE;MESITYLENESULPHONYL CHLORIDE
• CAS NO: 773-64-8
• Molecular Formula: C₉H₁₁ClO₂S
• Molecular Weight: 218.7
• EINECS: 212-257-8
• Product Categories: Carboxylic;Benzene derivates;Biochemistry;Condensation & Active Esterification;Condensing Agents (DNA / RNA Synthesis);Nucleosides, Nucleotides & Related Reagents;Protecting Agents, Phosphorylating Agents & Condensing Agents;Protection & Derivatization Reagents (for Synthesis);Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 773-64-8.mol

Chemical Properties

• Melting Point: 55-57 °C(lit.)
• Boiling Point: 150°C/20mm
• Flash Point: >230 °F
• Appearance: White to gray/Crystalline Powder
• Density: 1.4386 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Store at RT.
• Solubility: Soluble in toluene (almost transparency).
• Water Solubility: insoluble
• Sensitive: Moisture Sensitive
• BRN: 1107601
• CAS DataBase Reference: 2-Mesitylenesulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Mesitylenesulfonyl chloride(773-64-8)
• EPA Substance Registry System: 2-Mesitylenesulfonyl chloride(773-64-8)

Safety Data

• Hazard Codes: C
• Statements: 34-29
• Safety Statements: 22-26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: DB8930000
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 773-64-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Mesitylenesulfonyl chloride is used as a reagent for intramolecular lactamizations and lactonization, which are important reactions in the synthesis of various pharmaceutical compounds. It is particularly useful in the synthesis of cyclic peptides and other bioactive molecules.
Used in Chemical Synthesis:
2-Mesitylenesulfonyl chloride is used as a coupling reagent in polynucleotide synthesis, a process that is crucial for the production of nucleic acid-based drugs and diagnostic agents. It helps to facilitate the formation of phosphodiester bonds between nucleotides, leading to the formation of long chains of DNA or RNA.
Used in Peptide Synthesis:
2-Mesitylenesulfonyl chloride is used as a reagent for protecting guanidino groups and tryptophan during peptide synthesis. This protection allows for selective reactions to occur at other sites on the peptide, enabling the synthesis of complex peptide structures with multiple functional groups.
Used in Organic Chemistry Research:
2-Mesitylenesulfonyl chloride is a versatile reagent in organic chemistry research, where it is used in a variety of reactions, including esterification, acylation, and sulfonylation. Its reactivity and stability make it a valuable tool for the synthesis of a wide range of organic compounds.

InChI:InChI=1/C9H11ClO2S/c1-6-4-7(2)9(8(3)5-6)13(10,11)12/h4-5H,1-3H3

Upstream product

• 108-67-8 1,3,5-trimethyl-benzene 
• 7446-70-0 aluminium trichloride 
• 7791-25-5 sulfuryl dichloride 
• 7719-09-7 thionyl chloride 
• 3453-83-6 mesitylene sulfonic acid 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 16182-15-3 2,4,6-trimethylbenzenesulfonohydrazide 
• 6148-75-0 2,4,6-trimethylbenzenesulfonate sodium salt 

Downstream Products

• 113674-76-3 1-(2,4,6-trimethyl-benzenesulfonyl)-piperidine 
• 5465-84-9 phenyl 2,4,6-trimethylbenzenesulfonate 
• 1483-92-7 bis(2,4,6-trimethylphenyl)disulfide 
• 59057-35-1 2,4,6-trimethylbenzenesulphinic acid 
• 151915-07-0 N-ethyl-(2-mesitylene)sulfonamide 
• 59724-52-6 N-mesitylenesulfonyl ethanolamine 
• 349090-72-8 N,N,2,4,6-pentamethylbenzenesulfonamide 
• 13250-01-6 (2,4-dimethyl-phenyl)-mesityl sulfone 
• 106003-69-4 2,4,6-trimethyl-N-methylbenzenesulfonamide 
• 3112-79-6 dimesityl sulfone 
• 25111-64-2 3-(2,4,6-Trimethyl-benzolsulfonylamino)-propionsaeure-nitril 
• 58658-55-2 O-(2,4,6-trimethylphenylsulfonyl)-N,N-bis(trimethylsilyl)hydroxylamine 
• 54881-44-6 (+/-)-Mesitylenenolsulfonat 
• 42541-96-8 Methyl (Z)-7-<(3R)-3-Hydroxy-5-oxo-1-cyclopentenyl>-5-heptenoate 

Relevant articles and documents

N-(4-FLUOROPHENYL)-5-PHENYL-[1,2,4] TRIAZOLO [1,5-A] PYRIDINE-2-CARBOXAMIDE DERIVATIVES AND THEIR SYNTHESIS THEREOF

The present invention relates to the development of novel N-(4-fluorophenyl)-5-phenyl- [1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives for their different pharmacological activities. It particularly relates to the development of N-(4-fluorophenyl)-5-phenyl- [1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives as antiviral, anticancer, antifungal, hypoglycemic, anti-tubercular, sedative, anti-type 2 diabetes activity. It specifically relates to the N-(4-fluorophenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives for treatment of H37Rv and multidrug-resistant (MDR) strains of Mycobacterium tuberculosis (MTB). The present invention also relates to the process for synthesis of N-(4-fluorophenyl)- 5-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives. The invention further relates to method for treatment of method for treatment of diseases such as tuberculosis, type 2 diabetes, bacterial, viral and fungal infections. Invention addresses the challenges in working with chemical processes and products by inventing novel reaction methodology that can maximize the desired products and minimize by-products, designing new synthetic schemes that can simplify operations in chemical productions and seeking nontoxic reagent that are inherently environmentally and ecologically benign. Synthesis of novel N-(4- fluorophenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives is being employed to develop a novel synthetic methodology and their pharmacological applications. Novel series of N-(4-fluorophenyl)-5-phenyl-[1,2,4]triazolo[l,5-a]pyridine-2-carboxamide derivatives were designed synthesized evaluated for their in vitro anti-mycobacterial activity against H37Rv and multi-drug-resistant (MDR) strains of mycobacterium tuberculosis (MTB). All the synthesized compounds were characterized by spectroscopic methods like Mass, NMR and elemental analysis.

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur

We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.

Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate

A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides.

Substituted Disulfonamide Compounds

Substituted disulfonamide compounds corresponding to formula I: In which R1, R2, R3, R4a, R4b, R5a, R5b, R8, R9a, R9b, R10, R11, a, b, s, t and A have defined meanings, pharmaceutical compositions containing one or more such compounds, processes for preparing such compounds, and a method of using such compounds for the treatment or inhibition of pain and/or other conditions mediated by the bradykinin receptor 1 (BR1).

A new, mild preparation of sulfonyl chlorides

A new method was developed for the preparation of sulfonyl chlorides from sulfonic acids under neutral conditions using 2,4,6-trichloro-1,3,5-triazine as chlorinating agent.

Bispiperidines as antithrombotic agents

Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents

Catalytic kinetic resolution of 5-alkoxy-2(5H)-furanones

The kinetic resolution of racemic 5-alkoxy-2(5H)-furanones, using a chiral aminoalcohol catalyzed 1,4-addition of arylthiols, was examined. Using various butenolides it was shown that a γ-alkoxy substituent appears to be essential to reach high enantioselectivities whereas electron-donating substituents in the arylthiols also increase the selectivity. Cinchona alkaloids are the preferred catalysts for the kinetic resolution, with quinine and quinidine leading to the most efficient and selective thiol additions. A remarkable dilution effect and a strong dependency on the mode of addition of reactants were observed. Optimization studies are presented of the kinetic resolution of 5-methoxy-2(5H)-furanone 2 resulting in (R)-2 or (S)-2 with enantiomeric excesses exceeding 90%. A mechanism for the quinine (quinidine) catalyzed kinetic resolution is given.

CATALYTIC SULFONYLATION OF PHENOL BY STERICALLY HINDERED SULFONYL CHLORIDES

The sulfonylation of phenol by substituted arenesulfonyl chlorides XArSO2Cl in the presence of triethylamine in benzene was studied by potentiometric titration.A linear relation was obtained between the logaritmhs of the catalytic rate constants and the steric constants Eso of the substituents in the sulfonyl chloride.The contribution from the induction and steric effects of the substituents at position2 to the kinetics of the process was assessed.It was concluded that the steric effect plays a predominant role over the induction and resonance effects.