2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE CAS 39085-59-1

Introduction：Basic information about 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE CAS 39085-59-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE Basic information

• Product Name: 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE
• Synonyms: TRISYLHYDRAZIDE;TPSH;TRIISOPROPYLBENZENE SULFONYLHYDRAZIDE;2,4,6-triisopropylbenzenesulphonohydrazide;2,4,6-Triisopropyl benzenesulphonohydrazine;2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE;2,4,6-TRIISOPROPYL BENZENESULFONYL HYDRAZINE;2,4,6-TRIISOPROPYLBENZENESULFONO-HYDRAZIDE
• CAS: 39085-59-1
• MF: C15H26N2O2S
• MW: 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

2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE Chemical Properties

• Melting point: 110-112 °C (dec.) (lit.)
• Boiling point: 396.6±52.0 °C(Predicted)
• density: 1.075
• storage temp.: -20°C
• solubility: Chloroform (Slightly), Methanol (Slightly)
• form: Solid
• pka: 9.51±0.10(Predicted)
• color: Off-White
• Sensitive: Moisture Sensitive
• BRN: 2145001
• InChI: InChI=1S/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
• InChIKey: GBQCDUBJTLROBV-UHFFFAOYSA-N
• SMILES: C1(S(NN)(=O)=O)=C(C(C)C)C=C(C(C)C)C=C1C(C)C
• CAS DataBase Reference: 39085-59-1(CAS DataBase Reference)

Safety Information

• 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
• HS Code: 29350090
• Storage Class: 11 - Combustible Solids

2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE Usage And Synthesis

Chemical Properties

White crystal

Uses

As a reagent for generation of diimide

Uses

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.

Application

2,4,6-Triisopropylbenzenesulfonyl hydrazide is used as a diazene equivalent; condensed with ketones and aldehydes to form hydrazones that can be converted into reactive  intermediates such as diazoalkanes, carbenes, carbenium ions, alkyllithiums, or umpolung synthons.

Preparation

2,4,6-Triisopropylbenzenesulfonyl hydrazide may be prepared in 96% yield by treating commercially available 2,4,6-triisopropylbenzenesulfonyl  chloride with hydrazine hydrate in THF, being careful to keep the reaction and workup temperatures below or around 0 °C. The  solid can be dried in vacuo over P2O5 for 24 h.