2,4,6-Triisopropylbenzenesulfonohydrazide

Name: 2,4,6-Triisopropylbenzenesulfonohydrazide
Brand: ChemScene
Availability: InStock
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CAS No. 39085-59-1
Cat. No. CS-0068826
Purity≥97%
MDL No.MFCD00014750

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2,4,6-Triisopropylbenzenesulfonohydrazide|CS-0068826

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General Information

CAS No. 39085-59-1
Cat. No. CS-0068826
Purity ≥97%
MDL No. MFCD00014750
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₆N₂O₂S
Molecular Weight 298.44
Synonym(s) 2,4,6-Triisopropylbenzenesulfonyl hydrazide
SMILES O=S(C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C)(NN)=O

Description

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-Triisopropylbenzenesulfonohydrazide serves as a robust and bench-stable hydrazide reagent for the synthesis of sulfonamide-based building blocks. Its sterically encumbered triisopropylphenyl group enhances stability and facilitates purification, while the hydrazide functionality enables reliable coupling with carbonyl compounds to form hydrazones or participate in cyclization reactions. This compound functions effectively in standard organic transformations, offering high functional group tolerance and compatibility with diverse synthetic workflows.

Synthesis

Route1
- In-stock
  
  6553-96-4
- ~97%
- In-stock
  
  39085-59-1
References
- Yang, Ming-Hsiu; Matikonda, Siddharth S.; Altman, Ryan A. Organic Letters, 2013 , vol. 15, # 15 p. 3894 - 3897

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 72.19
LogP 3.2088
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Sulfonyl Hydrazide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2,4,6-Triisopropylbenzenesulfonohydrazide

CAS No. 39085-59-1

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