192198

2,4,6-Triisopropylbenzenesulfonyl hydrazide

90%

• Synonym(s): 2,4,6-Triisopropylbenzenesulfonohydrazide, TPSH, Trisylhydrazide
• Linear Formula: [(CH₃)₂CH]₃C₆H₂SO₂NHNH₂
• CAS Number: 39085-59-1
• Molecular Weight: 298.44
• Beilstein: 2145001
• EC Number: 254-282-7
• MDL number: MFCD00014750
• UNSPSC Code: 12352100
• PubChem Substance ID: 24851533
• NACRES: NA.22

Properties

• Assay: 90%
• form: powder
• mp: 110-112 °C (dec.) (lit.)
• functional group: hydrazine
• storage temp.: −20°C
• SMILES string: CC(C)c1cc(C(C)C)c(c(c1)C(C)C)S(=O)(=O)NN
• 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
• InChI key: UGRVYFQFDZRNMQ-UHFFFAOYSA-N

Description

Application

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.[1]
It can be used as a reagent to synthesize:

• Nitrogen-containing polycyclic compounds by intramolecular cyclopropanation of N-alkyl indoles/pyrroles.[2]
• Vinyl sulfones by sulfonylation reaction of vinyl bromides.[3]
• Nitrile derivatives from carbonyl compounds via formation of corresponding hydrazones.[4]

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves