96440-80-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
3-(tert-Butyl)-5-methyl-1H-pyrazole serves as a key building block in the creation of pharmaceuticals and agrochemicals. Its presence in these compounds is attributed to its stability and the steric hindrance it provides, which can influence the pharmacological properties and activity of the final products.
Used in Coordination Chemistry as a Ligand:
3-(tert-Butyl)-5-methyl-1H-pyrazole is utilized as a ligand in coordination chemistry due to its ability to form stable complexes with metal ions. This application is facilitated by the electron-donating nature of the tert-butyl and methyl groups, which enhance the compound's ligating properties.
Used in Organic Synthesis:
3-(tert-Butyl)-5-methyl-1H-pyrazole is employed as an intermediate in organic synthesis, where its reactivity and structural features are harnessed to produce a variety of organic compounds.
Used in Materials Science:
3-(tert-Butyl)-5-methyl-1H-pyrazole's unique structure makes it a valuable component in the development of new materials with specific properties, such as those with potential applications in catalysis, sensors, or advanced materials for various industries.

InChI:InChI=1/C8H14N2/c1-6-5-7(10-9-6)8(2,3)4/h5H,1-4H3,(H,9,10)

Upstream product

• 7307-04-2 acetylpinacolin 
• 33663-62-6 5-amino-2,2-dimethylhex-4-en-3-one 
• 563-41-7 semicarbazide hydrochloride 
• 1068-57-1 acetic acid hydrazide 
• 254734-52-6 (Z)-4-Amino-5,5-dimethyl-hex-3-en-2-one 
• 7400-27-3 tertbutylhydrazine hydrochloride 

Downstream Products

• 828283-34-7 3-(tert-butyl)-5-methyl-1-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

Discovery and SAR Evolution of Pyrazole Azabicyclo[3.2.1]octane Sulfonamides as a Novel Class of Non-CovalentN-Acylethanolamine-Hydrolyzing Acid Amidase (NAAA) Inhibitors for Oral Administration

Inhibition of intracellularN-acylethanolamine-hydrolyzing acid amidase (NAAA) activity is a promising approach to manage the inflammatory response under disabling conditions. In fact, NAAA inhibition preserves endogenous palmitoylethanolamide (PEA) from degradation, thus increasing and prolonging its anti-inflammatory and analgesic efficacy at the inflamed site. In the present work, we report the identification of a potent, systemically available, novel class of NAAA inhibitors, featuring a pyrazole azabicyclo[3.2.1]octane structural core. After an initial screening campaign, a careful structure-activity relationship study led to the discovery ofendo-ethoxymethyl-pyrazinyloxy-8-azabicyclo[3.2.1]octane-pyrazole sulfonamide50(ARN19689), which was found to inhibit human NAAA in the low nanomolar range (IC50= 0.042 μM) with a non-covalent mechanism of action. In light of its favorable biochemical, in vitro and in vivo drug-like profile, sulfonamide50could be regarded as a promising pharmacological tool to be further investigated in the field of inflammatory conditions.

Discovery of DS79182026: A potent orally active hepcidin production inhibitor

Hepcidin has emerged as the central regulatory molecule of systemic iron homeostasis. Inhibition of hepcidin could be a strategy favorable to treating anemia of chronic disease (ACD). We report herein the synthesis and structure-activity relationships (SARs) of a series of benzisoxazole compounds as orally active hepcidin production inhibitors. The optimization study of multi kinase inhibitor 1 led to a potent and bioavailable hepcidin production inhibitor 38 (DS79182026), which showed serum hepcidin lowering effects in a mouse IL-6 induced acute inflammatory model.

Palladium catalyzed addition of arylboronic acid or indole to nitriles: Synthesis of aryl ketones

Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.

Tris(pyrazolyl)phosphine oxides. Synthesis and coordination chemistry with copper(I)

A set of substituted tris(pyrazolyl)phosphine oxides (OP(pz x)3) has been prepared in high yield and applied as neutral scorpion-type ligands. The P apex provides a convenient spectroscopic handle. Substitution at the 3-position of the pyrazolyl ring influences the steric demands of the ligand, while substitution at the 5-position enhances the stability. Copper(I) acetonitrile complexes of the OP(pzx) 3 ligands were prepared and tested in ligand exchange reactions with PPh3 and CO. The v(CO) values of the carbonyl complexes demonstrate the electron-withdrawing properties of the ligands. These observations show that OP(pzx)3 ligands are an interesting extension of the widely used scorpion-type ligands.

Nitrogen-containing heterocycles from metal β-diketonates

Factors determining the reaction of metal β-diketonates with hydrazine, in particular the nature of central metal ion and structure of β-diketonate ligand, are discussed. The possibility for the preparation of other heterocyclic compounds via reaction of metal acetylacetonates with phenylhydrazine, o-phenylenediamine, urea, and thiourea was studied.

Pyrazole-tethered heteroditopic ligands and their transition metal complexes: Synthesis, structure, and reactivity

Various pyrazole-based P,N (2a-c) and N,N (3a-b) ligands have been synthesized. Using representative ligands, NiII, CoII, CuII, and CuI complexes have been prepared and structurally characterized by crystallogra

Pyrazole-tethered arylphosphine ligands for Suzuki reactions of aryl chlorides: How important is chelation?

Pyrazole-derived bidentate ligands (P,N-donor) with bulky substituents at the 3-position of the pyrazole, 1b-d, were used with Pd2(dba) 3 to carry out efficient Suzuki coupling reactions with both aryl bromides and chlorides. Enhanced catalytic activity on account of steric crowding in the metal complex suggested participation of a chelated structure in the intermediate catalytic steps.

5-Hydroxy-2-pyrazolines and some of their 1-substituted analogs

The use of 1,3-dicarbonyl compounds containing strong electron-withdrawing substituents (perfluoroalkyl, 4-nitrophenyl) at one of the carbonyl groups in reaction with hydrazine or its monosubstituted derivatives (4-nitro- and 2,4-dinitrophenylhydrazines) leads to the formation of stable intermediates for the synthesis of pyrazoles (5-hydroxy-2-pyrazolines) or their linear tautomers (hydrazones).

Reactions of β-aminoenones with acetylhydrazine, semicarbazide and methoxycarbonylhydrazine. Synthesis of 1-acetyl-, 1-carboxamide- or methyl 1- carboxylated pyrazole derivatives

Acetylhydrazine, semicarbazide and methoxycarbonylhydrazine react with β-aminoenones to give regioselectively the corresponding N-acetyl- or N- carboxypyrazole derivatives. The reaction are highly regioselective and occurs via 5-hydroxypyrazolines which in several case can be isolated and characterized.

β-Aminoenones in the regioselective synthesis of 1,3,5-trialkyl-pyrazoles. The influence of the substituents in the mechanism and the regioselectivity of the reaction

β-Aminoenones react with monoalkyl hydrazines to give regioselectively 1,3,5-trisubstituted pyrazoles. The mechanism and level of regioselectivity depend on both the substitution pattern of the substrates and the reaction conditions. When the least bulky