2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE

Base Information

• Chemical Name: 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE
• CAS No.: 39085-59-1
• Molecular Formula: C15H26N2O2S
• Molecular Weight: 298.45
• Hs Code.: 29350090
• European Community (EC) Number: 254-282-7
• NSC Number: 620119
• UNII: XE77ZV5VCV
• DSSTox Substance ID: DTXSID40192332
• Nikkaji Number: J261.302F
• Wikidata: Q56762047
• ChEMBL ID: CHEMBL1986656
• Mol file: 39085-59-1.mol

Synonyms:(2,4,6-Triisopropylbenzenesulfonyl)hydrazine;2,4,6-Triisopropylbenzenesulfonic acid hydrazide;2,4,6-Triisopropylbenzenesulfonohydrazide;2,4,6-Triisopropylbenzenesulfonyl hydrazide;2,4,6-Triisopropylphenylsulfonylhydrazine;NSC 620119;Trisylhydrazide;Trisylhydrazine;[(2,4,6-Triisopropylphenyl)sulfonyl] hydrazide;

Chemical Property of 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE

Chemical Property:

• Vapor Pressure: 1.68E-06mmHg at 25°C
• Melting Point: 110-112 °C (dec.)(lit.)
• Refractive Index: 1.52
• Boiling Point: 396.6 °C at 760 mmHg
• PKA: 9.51±0.10(Predicted)
• Flash Point: 193.7 °C
• Density: 1.075 g/cm³
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 298.17149925
• Heavy Atom Count: 20
• Complexity: 381

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

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)NN)C(C)C
• Uses: As a reagent for generation of diimide 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.

Technology Process of 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE

There total 2 articles about 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE 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: 97.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) → trisylhydrazine (39085-59-1)

Guidance literature:

With hydrazine; In tetrahydrofuran; at -10 - 0 ℃; for 3h;

DOI:10.1021/ol401637n

Reference yield: 95.0%

→ trisylhydrazine (39085-59-1)

Guidance literature:

With carbazic acid; In neat (no solvent); at 100 ℃; for 5h; Green chemistry;

Reference yield: 96.0%

trisylhydrazine (39085-59-1) + benzaldehyde (100-52-7) → benzaldehyde 2,4,6-tri-isopropylbenzenesulphonyl hydrazone (75142-62-0)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/jacs.6b11336

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

Downstream raw materials:

C₂₂H₃₈N₂O₂S

4-heptanone trisylhydrazone

camphor trisylhydrazone

cyclohexanone 2,4,6-triisopropylbenzenesulphonylhydrazone

Refernces

• 1、 -. "COMPOUND HAVING S1P5 RECEPTOR AGONIST ACTIVITY". Paragraph 0308. . Retrieved 2021/01/14.
• 2、 Li, Wei,Gao, Lingfeng,Zhuge, Wenyun,Sun, Xu,Zheng, Gengxiu. "Catalyst-free synthesis of 3-sulfone nitrile from sulfonyl hydrazides and acrylonitrile in water". supporting information. p. 7819 - 7823. Retrieved 2017/10/06.