39085-59-1

Basic information

• Product Name: 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE
• Synonyms: 2,4,6-Triisopropylbenzene-1-sulfonic acid hydrazide;2,4,6-Triisopropylbenzenesulfonic acid hydrazide;2,4,6-Tris(1-methylethyl)benzenesulfonic acid hydrazide;2,4,6-Triisopropylphenylsulfonyl hydrazine;2,4,6-Triisopropylbenzenesulphonohydrazide 95%;2,4,6-Tris(isopropyl)benzenesulphonohydrazide 95%;2,4,6-Tris(prop-2-yl)benzenesulphonohydrazide, TPSH;2,4,6-Triisopropylbenzenesulfonyl hydrazide 90%
• CAS NO: 39085-59-1
• Molecular Formula: C15H26N2O2S
• Molecular Weight: 298.44
• EINECS: 254-282-7
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonyl Hydrazides;Sulfur Compounds
• Mol File: 39085-59-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 110-112 °C (dec.)(lit.)
• Boiling Point: 396.6 °C at 760 mmHg
• Flash Point: 193.7 °C
• Appearance: /
• Density: 1.075
• Vapor Pressure: 1.68E-06mmHg at 25°C
• Refractive Index: 1.52
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.51±0.10(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 2145001
• CAS DataBase Reference: 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE(39085-59-1)
• EPA Substance Registry System: 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE(39085-59-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• RIDADR: UN 1325 4.1/PG III
• WGK Germany: 3
• F: 4.8-10
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 39085-59-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

Uses

Different sources of media describe the Uses of 39085-59-1 differently. You can refer to the following data:
1. As a reagent for generation of diimide
2. 2,4,6-Triisopropylbenzenesulfonyl hydrazide (TPSH) is a best source of diazene. It can be used as a selective reducing agent for the reduction of alkenes and other double bonds via in situ formation of diazene (diimide) in the presence of base. TPSH reduction method is efficiently used in the synthesis of polymers and natural products as it tolerates sensitive groups such as esters, ketones, or organometal complexes. It also undergoes condensation reaction with ketones and aldehydes to produce corresponding hydrazones that can be converted into reactive intermediates such as diazoalkanes, carbenes, carbenium ions, and alkyllithiums.It can be used as a reagent to synthesize: Nitrogen-containing polycyclic compounds by intramolecular cyclopropanation of N-alkyl indoles/pyrroles. Vinyl sulfones by sulfonylation reaction of vinyl bromides. Nitrile derivatives from carbonyl compounds via formation of corresponding hydrazones.

InChI:InChI=1/C15H26N2O2S/c1-9(2)12-7-13(10(3)4)15(20(18,19)17-16)14(8-12)11(5)6/h7-11,17H,16H2,1-6H3

Upstream product

• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 

Downstream Products

• 63883-66-9 2-methylcyclohexanone (2,4,6-triisopropylphenyl)sulphonylhydrazone 
• 63883-81-8 3-pentanone (2,4,6-triisopropylbenzenesulfonyl)hydrazone 
• 63883-62-5 octan-2-one 2,4,6-tri-isopropylbenzenesulphonylhydrazone 
• 63883-64-7 C₂₄H₃₄N₂O₂S 
• 140226-71-7 3-methyl-2-butanone-2,4,6-triisopropylbenzenesulfonyl-hydrazide 
• 64028-01-9 3,3-dimethyl-2-butanone-2,4,6-triisopropylbenzenesulfonyl-hydrazide 
• 104703-60-8 (E)-trisylhydrazone de l'isopropylidene-2 cyclopentanone-1 
• 174681-64-2 C₂₂H₃₈N₂O₂S 
• 127700-37-2 C₂₁H₃₃F₃N₂O₂S 
• 81470-98-6 2-oxohexadecanoic acid 2,4,6-tri-iso-propylbenzenesulphonylhydrazone 
• 127700-40-7 Trifluoroacetophenone trisylhydrazone 
• 389636-54-8 2,2-dimethyl-cyclohexanone 2,4,6-tri-isopropyl-benzenesulfonyl hydrazone 
• 80703-68-0 C₂₈H₅₀N₂O₃S 
• 77229-27-7 C₂₀H₃₄N₂O₃S 

Relevant articles and documents

Multiple on-resin olefin metathesis to form ring-expanded analogues of the lantibiotic peptide, Lacticin 3147 A2

Chemical synthesis of lantibiotic analogues wherein monosulfide bridges are replaced with other groups can shed light on structure-activity relationships and generate variants that are resistant to aerobic oxidation and have better metabolic stability. This work describes the first complete synthesis of a carbocyclic lantibiotic analogue 2, using sequential on-resin ring-closing olefin metathesis and solution-phase peptide synthesis. The methodology described should find wide application for the preparation of rigidified peptidomimetics containing multiple carbocyclic rings.

Total Syntheses of (-)-Englerins A/B, (+)-Orientalols E/F, and (-)-Oxyphyllol

(-)-Englerin A was synthesized in 20 steps from the commercially available material (R)-(+)-limonene. In addition, (-)-englerin B, (+)-orientalol E/F and (-)-oxyphyllol were obtained from the intermediate in the route. The key steps include a hydroxyl-directing stereoselective and regioselective intramolecular cyclopropanation and a multi-gram-scale stereoselective formal intramolecular [3 + 2] cross cycloaddition ([3 + 2]-IMCC) of a cyclopropane 1,1-diester with a carbonyl. A precursor of 7,10-diastereoisomer of englerins was also obtained.

Base-mediated tandem sulfonylation and oximation of alkenes in water

A base-mediated bifunctionalization of alkenes for the synthesis of α-sulfonylethanone oximes was developed in water under metal-free conditions. This reaction features a wide substrate scope and facile starting materials to afford the desired products in high yields.