36982-84-0

Basic information

• Product Name: 2,4,6-Triisopropylbenzene-sulfonyl azide
• Synonyms: 2,4,6-TRIISOPROPYLBENZENESULFONYL AZIDE;2,4,6-Triisopropylbenzenesulphonylazide;Trisyl azide;2,4,6-Triisopropylbenzenesulfonyl azide, 98%, stab. with ca 10% water;2,4,6-Triisopropylbenzenesulfonyl azide ,90% [stab. With ca 10% water];2,4,6-Triisopropylbenzenesulfonic acid azide;2,4,6-Triisopropylbe;2,4,6-Triisopropylp henylsulfonyl azide
• CAS NO: 36982-84-0
• Molecular Formula: C₁₅H₂₃N₃O₂S
• Molecular Weight: 309.43
• Product Categories: Azidation/Diazo Transfer;C-X Bond Formation (Non-Halogen);Various Azides;Azides;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Synthetic Reagents
• Mol File: 36982-84-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 40-42°C
• Flash Point: 4℃
• Appearance: /
• Refractive Index: n20/D1.499
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water.
• BRN: 2391566
• CAS DataBase Reference: 2,4,6-Triisopropylbenzene-sulfonyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Triisopropylbenzene-sulfonyl azide(36982-84-0)
• EPA Substance Registry System: 2,4,6-Triisopropylbenzene-sulfonyl azide(36982-84-0)

Safety Data

• Hazard Codes: T,Xn,F
• Statements: 36/37/38-25-67-65-48/20-38-22-11-63-5
• Safety Statements: 15-26-36-45-62-36/37-16-37
• RIDADR: UN1294 - class 3 - PG 2 - Toluene, solution
• WGK Germany: 3
• Hazardous Substances Data: 36982-84-0(Hazardous Substances Data)

Usage

Description

2,4,6-Triisopropylbenzene-sulfonyl azide is a white wet solid that serves as a versatile reagent in various chemical reactions and synthesis processes. It is particularly known for its ability to facilitate diazo transfer to ketones and azide transfer to potassium enolates, making it a valuable compound in the field of organic chemistry.

Uses

Used in Organic Chemistry:
2,4,6-Triisopropylbenzene-sulfonyl azide is used as a reagent for diazo transfer to ketones, particularly under phase-transfer conditions. This method provides better yields of sterically-hindered α-diazo ketones compared to other methods, making it a preferred choice for such reactions.
Used in Stereoselective Diversity-Oriented Synthesis:
In the field of stereoselective diversity-oriented synthesis, 2,4,6-Triisopropylbenzene-sulfonyl azide is employed for the synthesis of functionalized saccharides. Its unique properties allow for the creation of a wide range of stereoisomers, which are essential in various applications, including pharmaceuticals and materials science.
Used in Meyer's Lactamization:
2,4,6-Triisopropylbenzene-sulfonyl azide is also used as a reagent in Meyer's lactamization, a chemical reaction that involves the formation of a lactam ring from an ester and an amine. This process is crucial in the synthesis of various complex organic compounds.
Used in Pharmaceutical Applications:
2,4,6-Triisopropylbenzene-sulfonyl azide is used as a reagent for the synthesis of various pharmaceutical agents, including:
1. An antidote to anthrax lethal factor intoxication, which can help in the development of treatments for anthrax infections.
2. A bacterial RNA polymerase inhibitor, which can be used to develop new antibiotics targeting bacterial infections.
3. Bicyclic extended dipeptide surrogates, which are important in the development of novel peptide-based drugs.
4. Single enantiomers of mycobacterial ketomycolic acids, which are essential in the synthesis of anti-tuberculosis drugs.

InChI:InChI=1/C15H23N3O2S/c1-9(2)12-7-13(10(3)4)15(14(8-12)11(5)6)21(19,20)18-17-16/h7-11H,1-6H3

Upstream product

• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 39085-59-1 trisylhydrazine 

Downstream Products

• 135387-94-9 C₄₇H₅₂N₄O₇S 
• 139348-02-0 3-[4-Oxo-1-(2,4,6-triisopropyl-benzenesulfonyloxy)-azetidin-2-yl]-propionic acid 2-trimethylsilanyl-ethyl ester 
• 194302-48-2 (1S,2S)-1,2-bis[(1S)-azido-2-oxo-2((4S)-benzyl-2-oxo-3-oxazolidinyl)ethyl]cyclopropane 

Relevant articles and documents

Microchannel synthesis method of aryl sulfonyl azide

The invention discloses a microchannel synthesis method of aryl sulfonyl azide. Sodium azide and water are uniformly stirred and prepared into a material A, aryl sulfonyl chloride and acetone are uniformly stirred and prepared into a material B, and the material A and the material B are continuously fed into a microchannel reactor at the flow rate of 6mL/min-70mL/min and efficiently react to prepare the aryl sulfonyl azide. Compared with the prior art, the microchannel synthesis method has the advantages that process route operation is safe, conversion rate is high, cost is saved, and the yield of the aryl sulfonyl azide is higher than 80%.

Photoinduced Cascade Reaction of Tertiary Amines with Sulfonyl Azides: Synthesis of Amidine Derivatives

A metal-free cascade reaction of tertiary amines with sulfonyl azides promoted by acridinium salts under blue light irradiation was developed and provided amidine derivatives in moderate to good yields. Enamine was generated from tertiary amine via single-electron transfer promoted by acridinium salts, and the following [3+2] cyclization with sulfonyl azide and CH2N2 release afforded the desired products. (Figure presented.).

Access to the aeruginosin serine protease inhibitors through the nucleophilic opening of an oxabicyclo[2.2.1]heptane: Total synthesis of microcin SF608

Serine proteases play key roles in many biological processes and are associated with several human diseases such as thrombosis or cancer. During the search for selective inhibitors of serine proteases, a family of linear peptides named the aeruginosins was discovered in marine cyanobacteria. We herein report an entry route into the synthetically challenging core fragment of these natural products. Starting from the common oxabicyclic building block 11, we accessed the octahydroindole core of the aeruginosins, exemplified by the total synthesis of microcin SF608 (2). Key to the synthetic strategy is a highly efficient nucleophilic opening of an oxabicyclo[2.2.1]heptane producing the hydroindole motif of microcin SF608. Moreover, during the synthetic efforts we have observed an unusual regioselective epoxide reduction. Detailed experimental studies of this reaction led us to propose a mechanistic rationale involving intramolecular hydrogen atom delivery by a carbamate NH group to control the regioselectivity of the homolytic epoxide cleavage. Expect the unexpected! An entry route to the aeruginosin protease inhibitors is reported and showcased on the total synthesis of microcin SF608 (see scheme). Detailed experimental studies of an unusual regioselective epoxide reduction observed during this synthesis suggests a mechanistic rationale for this transformation involving intramolecular hydrogen atom delivery by a carbamate NH to direct the regioselectivity of the homolytic epoxide cleavage.