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Sigma-Aldrich

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:
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

Assay

90%

form

powder

mp

110-112 °C (dec.) (lit.)

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

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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:
  • 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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
2,4,6-Triisopropylbenzenesulfonylhydrazide
Chamberlin AR, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition null
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-Tri-isopropylbenzenesulphonyl hydrazide: A convenient source of di-imide
Cusack NJ, et al.
Tetrahedron, 32(17) (1976)
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