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

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

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 
• 174698-36-3 (+/-)3-azido-2,3-dihydro-1-[4-methoxybenzyl]-2-oxo-5-phenyl-1H-1,4-benzodiazepine 
• 177954-77-7 3-Azido-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepine 
• 170291-48-2 methyl α-diazo-3,5-bis(trifluoromethyl)benzeneacetate 
• 960209-73-8 1,1'-bis(N-triphenylphosphoranilideneamino)ruthenocene 
• 159948-08-0 3-(2(S)-azido-11-benzyloxycarbonylamino-n-undecanoyl)-4(S)-(phenylmethyl)-2-oxazolidinone 

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%.

Palladium(0)-Catalyzed Carbonylative Synthesis of N-Acylsulfonamides via Regioselective Acylation

N-Acylsulfonamides represent an important bioisostere of carboxylic acids that allow for greater molecular elaboration and enhanced hydrogen bonding capabilities. Herein, we present a mild and convenient palladium(0)-catalyzed synthesis of N-acylsulfonamides via the carbonylative coupling of sulfonyl azides and electron-rich heterocycles. The reaction proceeds via in situ generation of a sulfonyl isocyanate followed by regioselective acylation of an indole or pyrrole nucleophile. This approach has been used to synthesize 34 indole- and pyrrole-substituted N-acylsulfonamides in yields of up to 95%. Importantly, this process is ligand-free and compatible with an ex situ solid CO source and requires only slightly elevated temperatures, making it a highly attractive method for the preparation of this important class of compounds. This study further investigated the possibility of labeling N-acylsulfonamides with carbon-11 to facilitate biological evaluation and in vivo studies with positron emission tomography.

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.).

Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature

A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

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.

Cu-catalyzed multicomponent polymerization to synthesize a library of poly(N -sulfonylamidines)

We report a versatile Cu-catalyzed multicomponent polymerization (MCP) technique that enables the synthesis of high-molecular-weight, defect-free poly(N-sulfonylamidines) from monomers of diynes, sulfonyl azides, and diamines. Through a series of optimizations, we discovered that the addition of excess triethylamine and the use of N,N′-dimethylformamide as a solvent are key factors to ensure efficient MCP. Formation of cyclic polyamidines was a side reaction during polymerization, but it was readily controlled by using diynes or diamines with long or rigid moieties. In addition, this polymerization is highly selective for three-component reactions over click reactions. The combination of the above factors enables the synthesis of high-molecular-weight polymers, which was challenging in previous MCPs. All three kinds of monomers (diynes, sulfonyl azides, and diamines) are readily accessible and stable under the reaction conditions, with various monomers undergoing successful polymerization regardless of their steric and electronic properties. Thus, we synthesized various high-molecular-weight, defect-free polyamidines from a broad range of monomers while overcoming the limitations of previous MCPs, such as low conversion and defects in the polymer structures.

α-Azido bisphosphonates: Synthesis and nucleotide analogues

The first examples of α-azido bisphosphonates [(RO) 2P(O)]2CXN3 (1, R = i-Pr, X = Me; 2, R = i-Pr, X = H; 3, R = H, X = Me; 4, R = H, X = H) and corresponding β,γ- CXN3 dGTP (5-6) and α,β-CXN3 dATP (7-8) analogues are described. The individual diastereomers of 7 (7a/b) were obtained by HPLC separation of the dADP synthetic precursor (14a/b).

SULFONAMIDE COMPOUNDS

Certain sulfonamide compounds are dual CCK1/CCK2 inhibitors useful in the treatment of CCK1/CCK2 mediated diseases.

SILINANE COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS

The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is also directed to pharmaceutical compositions comprising these compounds and processes for preparing them. The present invention is also directed to the use of these inhibitors in combination with a therapy that causes a deleterious immune response in patients receiving the therapy.

Process for the preparation of D(-) and L(+)-3,3-diphenylalanine and D(-) and L(+)-substituted 3,3-diphenylalanines and derivatives thereof

A process for the preparation of D(-) and L(+)-3,3-diphenylalanine and D(-) and L(+)-substituted 3,3-diphenylalanines is described where N-protected DL-3,3-diphenylalanine or N-protected-DL-substituted 3,3-diphenylalanine are treated with (-)cinchonidine and the resulting salt resolved into the desired enantiomers, as well as derivatives thereof and valuable intermediates used in the process.