2,4,6-Triisopropylbenzenesulfonyl chloride

Base Information

• Chemical Name: 2,4,6-Triisopropylbenzenesulfonyl chloride
• CAS No.: 6553-96-4
• Molecular Formula: C15H23ClO2S
• Molecular Weight: 302.865
• Hs Code.: 29049020
• European Community (EC) Number: 229-479-6
• NSC Number: 102803
• UNII: 4QZ3QZX6G4
• DSSTox Substance ID: DTXSID30215827
• Nikkaji Number: J124.143E
• Wikidata: Q72513624
• Mol file: 6553-96-4.mol

Synonyms:2,4,6-TIPBS;2,4,6-triisopropylbenzenesulfonyl;2,4,6-triisopropylbenzenesulfonyl chloride

Chemical Property of 2,4,6-Triisopropylbenzenesulfonyl chloride

Chemical Property:

• Appearance/Colour: White to cream solid
• Vapor Pressure: 9.55E-05mmHg at 25°C
• Melting Point: 92-94 °C(lit.)
• Refractive Index: 1.505
• Boiling Point: 349.3 °C at 760 mmHg
• Flash Point: 165.1 °C
• PSA: 42.52000
• Density: 1.096 g/cm³
• LogP: 6.06510
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Solubility.: ethanol: 50 mg/mL, clear
• Water Solubility.: decomposes
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 302.1107288
• Heavy Atom Count: 19
• Complexity: 363

Purity/Quality:

98% ^*data from raw suppliers

2,4,6-Triisopropylbenzenesulfonyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-29
• Safety Statements: 26-36/37/39-45-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1=CC(=C(C(=C1)C(C)C)S(=O)(=O)Cl)C(C)C
• Uses: 2,4,6-Triisopropylbenzenesulfonyl chloride is used for the synthesis of glycerophospholipids as a condensing agent and in the analysis of phosphonolipids in egg yolk by HPLC/MS technique. It acts as a coupling reagent for the synthesis of oligonucleotides and as sulfonates of pyrimidine nucleosides. It also serves as a condensing agent in the synthesis of hydrogen-phosphonate diesters. 2,4,6-Triisopropylbenzenesulfonyl chloride can be used in the analysis of phosphonolipids in eggyolk by HPLC/MS technique. It can also be used to synthesize:Dimeric neomycin-neomycin conjugate with a flexible linker, 2,2′-(ethylenedioxy)bis(ethylamine).Coupling reagents for the synthesis of oligonucleotides.Sulfonates of pyrimidine nucleosides. These sulfonates can be displaced by nucleophiles in the presence of palladium-catalysts.

Technology Process of 2,4,6-Triisopropylbenzenesulfonyl chloride

There total 2 articles about 2,4,6-Triisopropylbenzenesulfonyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

1,3,5-triisopropyl benzene (717-74-8) → 2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4)

Guidance literature:

With chlorosulfonic acid; In chloroform; at 0 ℃;

DOI:10.1021/jo971093e

Reference yield:

→ 2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4)

Guidance literature:

Reference yield: 100.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 1-(Trimethylsilyl)imidazole (18156-74-6) → 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole (50257-40-4)

Guidance literature:

In dichloromethane; for 1h; Ambient temperature;

upstream raw materials:

1,3,5-triisopropyl benzene

Downstream raw materials:

2,4,6-Triisopropylthiophenol

3-(2,4,6-Triisopropyl-benzolsulfonylamino)-propionsaeure-nitril

ethyl-2,4,6-tri-isopropylbenzenesulphonate

1,2-bis(2,4,6-triisopropylphenyl)disulfane

Refernces

New Derivatives of Kanamycin B Obtained by Modifications and Substitutions in Position 6''. 1. Synthesis and Microbiological Evaluation

10.1021/jm00108a035

This research aimed to explore the impact of modifying the hydrophobic/hydrophilic balance at a specific site of an aminoglycoside antibiotic, specifically kanamycin B, by chemically modifying its 6" position through substitution with various groups including halogens, pseudohalogens, amino, amido, thioalkyl, and alkoxy groups. The study sought to understand how these modifications affected the antibacterial activity and toxicity of the derivatives. The conclusions drawn from the research indicated that only derivatives with small substituents in position 6", such as chloro, bromo, azido, amino, and methylcarbamido, showed acceptable antibacterial activity. A negative correlation was observed between the size of the 6" substituent and antibacterial activity against both Gram-positive and Gram-negative organisms sensitive to kanamycin B. The chemicals used in the process included kanamycin B, tert-butoxycarbonyl (BOC) as an N-protective group, 2,4,6-triisopropylbenzenesulfonyl chloride (TIBS-Cl) for sulfonylation, various nucleophiles for substitution reactions, and a range of reagents for the synthesis of different 6"-substituted kanamycin B derivatives.

Sucrose Chemistry. A Synthetically Useful Monoarenesulfonation

10.1021/jo00180a005

The research focuses on the selective monoarenesulfonation of sucrose, specifically the reaction with 2,4,6-triisopropylbenzenesulfonyl chloride (tripsyl chloride), which preferentially occurs at the 6'-OH group, yielding 6'-O-tripsylsucrose (2a) with a 39% yield without the need for chromatography. The study aimed to determine the substitution patterns at positions 6, 6', and 1' of sucrose and to establish the relative reactivities of the primary hydroxyl groups at these positions. The conclusions drawn from the research include the successful synthesis and characterization of 6'-O-tripsylsucrose and other related compounds, as well as the determination of the reactivity ratios of the primary hydroxyl groups (6':6:1' = 3.5:1.0:0.16).