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)

pka

9.51±0.10(Predicted)

form 

Solid

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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.

2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE(39085-59-1)Related Product Information

• 2,4,6-Trimethylbenzenesulfonyl hydrazide
• 4-Ethylbenzenesulfonamide
• 2,4-Dimethylbenzenethiol
• 1,3,5-Triisopropylbenzene
• 2,4,6-TRIISOPROPYLBENZENESULFONAMIDE
• METHANESULFONYL HYDRAZIDE
• 2,6-DIMETHYLTHIOPHENOL
• Benzenesulfonyl hydrazide
• 4-Methylbenzenesulfonhydrazide
• 1,3,5-TRIETHYLBENZENE
• 2,4,6-TRIMETHYLTHIOPHENOL
• 2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE
• (4-Isopropyl)thiophenol
• 2-Methylbenzene-1-sulfonamide
• antioxidant 1024
• Benzenesulfonamide, 4-(1-methylethyl)- (9CI)
• TRIFLUOROACETYLTRIPHENYLSILANE 2,4,6-TRIISOPROPYLBENZENESULFONYLHYDRAZONE
• Benzenesulfonamide, 2,4,6-trimethyl- (9CI)