6553-96-4

Basic information

• Product Name: 2,4,6-Triisopropylbenzenesulfonyl chloride
• Synonyms: TPSCL 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE;2,4,6-TRIISOPROPYLBENZENESULFONYL CHLORI;Triisopropylbenzenesulfonyl chlorid;2,4,6-Triisopropylbenzene-1-sulfonyl chloride;2,4,6-three isopropylbenzene sulfonyl chloride;2,4,6-Triisopropylbenzenesulfonyl chloride 97%;2,4,6-Triisopropylbenzenesulfonyl chloride≥ 99% (Titration);2,4,6-TRIISOPROPYLBENZENSULFONYL CHLORIDE
• CAS NO: 6553-96-4
• Molecular Formula: C₁₅H₂₃ClO₂S
• Molecular Weight: 302.86
• EINECS: 229-479-6
• Product Categories: Sulfonyl Halides;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;API intermediates;Biochemistry;Condensation & Active Esterification;Condensing Agents (DNA / RNA Synthesis);Nucleosides, Nucleotides & Related Reagents;Protecting Agents, Phosphorylating Agents & Condensing Agents;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 6553-96-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 92-94 °C(lit.)
• Boiling Point: 378C
• Flash Point: 165.1 °C
• Appearance: White to slightly beige/Crystalline Solid
• Density: 1.1012 (estimate)
• Vapor Pressure: 9.55E-05mmHg at 25°C
• Refractive Index: 1.505
• Storage Temp.: Store at RT.
• Solubility: ethanol: 50 mg/mL, clear
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• BRN: 1218575
• CAS DataBase Reference: 2,4,6-Triisopropylbenzenesulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Triisopropylbenzenesulfonyl chloride(6553-96-4)
• EPA Substance Registry System: 2,4,6-Triisopropylbenzenesulfonyl chloride(6553-96-4)

Safety Data

• Hazard Codes: C
• Statements: 34-29
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 6553-96-4(Hazardous Substances Data)

Usage

Description

2,4,6-Triisopropylbenzenesulfonyl chloride is an organic compound characterized by its triisopropylbenzene core and sulfonyl chloride functional group. It is a versatile reagent in organic synthesis and has unique properties due to its bulky isopropyl groups, which can influence its reactivity and selectivity in various chemical reactions.

Uses

Used in Pharmaceutical and Biochemical Research:
2,4,6-Triisopropylbenzenesulfonyl chloride is used as a condensing agent for the synthesis of glycerophospholipids, which are essential components of cell membranes and play crucial roles in cellular signaling and function.
Used in Analytical Chemistry:
In the analysis of phosphonolipids in egg yolk, 2,4,6-Triisopropylbenzenesulfonyl chloride is utilized in conjunction with the HPLC/MS technique, enabling the separation and detection of these important biomolecules.
Used in Nucleic Acid Chemistry:
2,4,6-Triisopropylbenzenesulfonyl chloride acts as a coupling reagent for the synthesis of oligonucleotides, which are short DNA or RNA molecules with applications in molecular biology, diagnostics, and therapeutics.
Used in Organic Synthesis:
2,4,6-Triisopropylbenzenesulfonyl chloride serves as a condensing agent in the synthesis of hydrogen-phosphonate diesters, which are analogs of phosphate esters and can be used as biochemical tools or potential pharmaceutical agents.
Used in the Synthesis of Conjugates:
2,4,6-Triisopropylbenzenesulfonyl chloride can be used to synthesize dimeric neomycin-neomycin conjugates with a flexible linker, such as 2,2′-(ethylenedioxy)bis(ethylamine), which may have applications in drug development or as research tools.
Used in the Synthesis of Sulfonates:
As a reagent, 2,4,6-Triisopropylbenzenesulfonyl chloride is used to prepare sulfonates of pyrimidine nucleosides. These sulfonates can be further transformed by nucleophilic displacement in the presence of palladium catalysts, providing a route to various modified nucleosides with potential applications in medicinal chemistry and chemical biology.

InChI:InChI=1/C15H23ClO2S/c1-9(2)12-7-13(10(3)4)15(19(16,17)18)14(8-12)11(5)6/h7-11H,1-6H3

Upstream product

• 717-74-8 1,3,5-triisopropyl benzene 

Downstream Products

• 114021-22-6 3',5'-Bis-O-(tert-butyldimethylsilyl)-4-O-<(2,4,6-triisopropylphenyl)sulfonyl>thymidine 
• 83906-31-4 5'-O-2,4,6-triisopropylbenzenesulfonyl-2',3'-O-dibenzoyluridine 
• 247923-41-7 (-)-(1S,2S)-N-(2,4,6-triisopropybenzenesulfonyl)-1,2-diphenylethylenediamine 
• 953395-49-8 6''-(2,4,6-triisopropylbenzenesulfonyl)-1,3,6',3''-tetra-N-(tert-butoxycarbonyl)kanamycin A 
• 304021-28-1 C₅₀H₇₂N₂O₈S₂ 
• 241820-93-9 1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin 
• 255375-04-3 3-(3-Cyano-phenyl)-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propionic acid 
• 255374-80-2 Nα-2,4,6-Triisopropylphenylsulfonyl-(L)-3-cyano-phenylalanine 
• 460745-02-2 (2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate 
• 636596-81-1 (2S,5S,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate 
• 171502-63-9 3-O-benzyl-6-O-(triisopropylbenzenesulfonyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 149035-74-5 O⁶-((2,4,6-Triisopropylphenyl)sulfonyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine 

Relevant articles and documents

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.

Organocatalytic asymmetric mannich reactions of 5H-oxazol-4-ones: Highly enantio- and diastereoselective synthesis of chiral α-alkylisoserine derivatives

The first organocatalytic Mannich reaction of 5H-oxazol-4-ones with various readily prepared aryl- and alkylsulfonimides has been developed. Two commercially available pseudoenantiomeric Cinchona alkaloids-derived tertiary amine/ureas have been demonstrated as the most efficient catalysts to access the opposite enantiomers of the Mannich products with equally excellent enantio- and diastereoselectivities. From the Mannich adducts, important α-methyl-α-hydroxy-β-amino acid derivatives, such as the α-methylated C-13 side chain of taxol and taxotere, can be conveniently prepared. Copyright

Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones

The diastereoselectivity of intermolecular β-addition of alkyl radicals to 2-(arylsulfinyl)-2-cycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of 2-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3,5-di-tert-butyl-4-methoxyphenyl)sulfinyl, (2,4,6-triisopropylphenyl)sulfinyl or (2,4,6-trimethylphenyl)sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2-(arylsulfinyl)-1-cyclohexanones in excellent yields and with high diastereoselectivity. Both the X-ray crystallographic analysis and the NOE experiment in the 1H NMR spectrum of (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]- and (S)-2-[(2,4,6-trimethylphenyl)sulfinyl]-2-cyclopentenone reveal an effective shielding of one of the olefin faces at the β-position by o-isopropyl and o-methyl groups. The addition of bidentate Lewis acids reverses the stereoselection through chelating the intermediates to give the addition products with high diastereoselectivity.