192198
2,4,6-Triisopropylbenzenesulfonyl hydrazide
90%
Synonym(s):
2,4,6-Triisopropylbenzenesulfonohydrazide, TPSH, Trisylhydrazide
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About This Item
Linear Formula:
[(CH3)2CH]3C6H2SO2NHNH2
CAS Number:
Molecular Weight:
298.44
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
254-282-7
Beilstein/REAXYS Number:
2145001
MDL number:
Assay:
90%
Form:
powder
InChI key
UGRVYFQFDZRNMQ-UHFFFAOYSA-N
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
SMILES string
CC(C)c1cc(C(C)C)c(c(c1)C(C)C)S(=O)(=O)NN
assay
90%
form
powder
mp
110-112 °C (dec.) (lit.)
functional group
hydrazine
storage temp.
−20°C
Quality Level
Related Categories
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.
It can be used as a reagent to synthesize:
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Synthesis and x-ray crystal structure of anti-dithia [3.3](2.6) triquinacenophane.
Roberts WP and Shoham G.
Tetrahedron Letters, 22(49), 4895-4898 (1981)
The asymmetric synthesis of cyclopentane derivatives by palladium-catalyzed coupling of prochiral alkylboron compounds.
Cho SY and Shibasaki M.
Tetrahedron Asymmetry, 9(21), 3751-3754 (1998)
Silver-promoted synthesis of vinyl sulfones from vinyl bromides and sulfonyl hydrazides in water
Zhang G, et al.
Chemical Communications (Cambridge, England), 56(34), 4688-4691 (2020)
Cobalt (II) Porphyrin-Catalyzed Intramolecular Cyclopropanation of N-Alkyl Indoles/Pyrroles with Alkylcarbene: Efficient Synthesis of Polycyclic N-Heterocycles
Reddy AR, et al.
Angewandte Chemie (International ed. in English), 55(5), 1810-1815 (2016)
2,4,6-Triisopropylbenzenesulfonylhydrazide
Chamberlin AR, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition null
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