2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE Property

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

InChIKey

GBQCDUBJTLROBV-UHFFFAOYSA-N

CAS DataBase Reference

39085-59-1(CAS DataBase Reference)

Safety

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

2,4,6-TRIISOPROPYLBENZENESULFONYL HYDRAZIDE Chemical Properties,Usage,Production

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.