4023-79-4

Basic information

• Product Name: 1-P-TOLYLBUTANE-1,3-DIONE
• Synonyms: 1-P-TOLYLBUTANE-1,3-DIONE;1-(4-METHYLPHENYL)BUTANE-1,3-DIONE;P-METHYLBENZOYLACETONE;1,3-butanedione, 1-(4-methylphenyl)-;1-P-Toylbutane-1,3-dione;4-Methylbenzoylacetone
• CAS NO: 4023-79-4
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• Product Categories: pharmacetical
• Mol File: 4023-79-4.mol

Chemical Properties

• Melting Point: 53 °C
• Boiling Point: 287.1 °C at 760 mmHg
• Flash Point: 106.9 °C
• Appearance: /
• Density: 1.052 g/cm³
• Vapor Pressure: 0.00253mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.96±0.10(Predicted)
• CAS DataBase Reference: 1-P-TOLYLBUTANE-1,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-P-TOLYLBUTANE-1,3-DIONE(4023-79-4)
• EPA Substance Registry System: 1-P-TOLYLBUTANE-1,3-DIONE(4023-79-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 4023-79-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-P-Tolylbutane-1,3-dione is used as a key intermediate for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be incorporated into the development of new drugs, enhancing their therapeutic properties and effectiveness.
Used in Perfumery Industry:
1-P-Tolylbutane-1,3-dione is used as a fragrance ingredient in the production of perfumes. Its sweet, floral scent contributes to the creation of unique and appealing fragrances, adding depth and complexity to perfume compositions.
Used in Chemical Synthesis:
1-P-Tolylbutane-1,3-dione serves as a building block in organic synthesis, enabling the production of a wide range of chemical compounds. Its reactivity and compatibility with various chemical groups make it a valuable component in the synthesis of complex organic molecules.
Used as a Reagent in Chemical Reactions:
1-P-Tolylbutane-1,3-dione is utilized as a reagent in various chemical reactions, facilitating the formation of desired products and improving the efficiency of the reaction processes. Its versatility as a reagent contributes to its importance in the chemical industry.

InChI:InChI=1/C11H12O2/c1-8-3-5-10(6-4-8)11(13)7-9(2)12/h3-6H,7H2,1-2H3

Upstream product

• 108-24-7 acetic anhydride 
• 122-00-9 para-methylacetophenone 
• 108-88-3 toluene 
• 141-78-6 ethyl acetate 
• 75-36-5 acetyl chloride 
• 1202238-17-2 C₁₃H₁₄O₃ 
• 201230-82-2 carbon monoxide 
• 624-31-7 4-tolyl iodide 
• 67-64-1 acetone 
• 106-38-7 para-bromotoluene 
• 855365-55-8 3-(4-methylbenzoyl)pentane-2,4-dione 
• 104-87-0 4-methyl-benzaldehyde 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 4211-89-6 3-methyl-5-(4-methylphenyl)isoxazole 
• 90861-52-2 3-methyl-5-(4-methylphenyl)-1H-pyrazole 
• 99-94-5 p-Toluic acid 
• 477320-28-8 2-hydroxy-4-methyl-6-p-tolyl-nicotinonitrile 
• 858019-19-9 1,4-dimethyl-2-oxo-6-p-tolyl-1,2-dihydro-pyridine-3-carbonitrile 
• 13298-57-2 2-diazo-1-(p-tolyl)butane-1,3-dione 
• 4475-61-0 3-methyl-5-p-tolyl-2⁽⁶⁾H-[1,2,6]thiadiazine 1,1-dioxide 
• 95346-55-7 C₁₇H₁₄N₃O₈^(1-) 
• 76387-94-5 4-Methyl-1-phenyl-6-p-tolyl-1H-pyrimidin-2-one 
• 76387-89-8 6-methyl-1-phenyl-4-(p-tolyl)pyrimidin-2(1H)-one 
• 88222-75-7 2-(2-Methyl-5-phenyl-2,3-dihydro-[1,3,4]thiadiazol-2-yl)-1-p-tolyl-ethanone 
• 95081-30-4 (6-Bromo-3-methyl-4H-benzo[1,4]thiazin-2-yl)-p-tolyl-methanone 
• 128609-00-7 3-Methyl-2-(4-methyl-benzoyl)-4H-benzo[1,4]thiazine-6-sulfonic acid 
• 113445-87-7 3--1,2,3-triphenylcyclopropene 

Relevant articles and documents

I2-Promoted [3+2] Cyclization of 1,3-Diketones with Potassium Thiocyanate: a Route to Thiazol-2(3H)-One Derivatives

An I2-promoted strategy has been developed for the synthesis of thiazol-2(3H)-one derivatives from 1,3-diketones with potassium thiocyanate. This [3+2] cyclization reaction involves C?S and C?N bond formation and exhibits good functional group tolerance. A series of thiazol-2(3H)-one derivatives are obtained in moderate to good yields. (Figure presented.).

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors

Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.

Direct synthesis of 2,3,5-trisubstituted pyrroles: via copper-mediated one-pot multicomponent reaction

We have developed a copper-mediated one-pot synthesis of 2,3,5-trisubstituted pyrroles from 1,3-dicarbonyl compounds and acrylates using ammonium acetate as a nitrogen source. The reaction achieves C-C and C-N bond formation and provides an efficient approach to access highly functionalized pyrroles without further raw material preparation. This method is operationally simple, compatible with a wide range of functional groups, and provides the target products in moderate to good yields. This journal is

Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants

Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.

Direct Access to Functionalized Indoles via Single Electron Oxidation Induced Coupling of Diarylamines with 1,3-Dicarbonyl Compounds

Under aerobic copper catalysis, an unprecedented direct synthesis of functionalized indoles via single electron oxidation induced coupling of diarylamines with 1,3-dicarbonyl compounds is presented. The protocol proceeds with good functional group and substrate compatibility, the use of readily available feedstocks and naturally abundant catalyst system, high step and atom efficiency, as well as selectivity, which offers a platform for accessing a new class of indoles with the potential for the discovery of functional molecules.

Design, synthesis and biological evaluation of novel hydroxamic acid based histone deacetylase 6 selective inhibitors bearing phenylpyrazol scaffold as surface recognition motif

In recent years, inhibition of HDAC6 became a promising therapeutic strategy for the treatment of cancer and HDAC6 inhibitors were considered to be potent anti-cancer agents. In this work, celecoxib showed moderate degree of HDAC6 inhibition activity and selectivity in preliminary enzyme inhibition activity assay. A series of hydroxamic acid derivatives bearing phenylpyrazol moiety were designed and synthesized as HDAC6 inhibitors. Most compounds showed potent HDAC6 inhibition activity. 11i was the most selective compound against HDAC6 with IC50 values of 0.020 μM and selective factor of 101.1. Structure-activity relationship analysis indicated that locating the linker group at 1′ of pyrazol gave the most selectivity. The most compounds 11i (GI50 = 3.63 μM) exhibited 6-fold more potent than vorinostat in HepG2 cells. Considering of the high selectivity against HDAC6 and anti-proliferation activity, such compounds have potential to be developed as anti-cancer agents.

Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof

The invention discloses a pyrazole compound containing N-aryl sulfonate. A structural formula of the pyrazole compound is shown in the description. Proofed by pharmacological study, the pyrazole compound has the advantages that the activity of cyclooxygenase 2 is inhibited; the high-efficiency inhibition function on the generation of cyclooxygenase 2 due to inflammation mediums is realized, so that the pyrazole compound can be used as an active matter, and the prepared anti-inflammation medicine can be used for treating the inflammations, such as rheumatic arthritis and rheumatalgia, and the diseases and symptoms, such as fevers.

Rhodium(ii)-catalysed generation of cycloprop-1-en-1-yl ketones and their rearrangement to 5-aryl-2-siloxyfurans

Donor-acceptor cyclopropenes formed from enoldiazoketones undergo catalytic rearrangement to 5-aryl-2-siloxyfurans via a novel mechanism that involves a nucleophilic addition of the carbonyl oxygen to the rhodium-activated cyclopropene.

Method for preparing celecoxib by using one-pot method

The invention discloses a method for preparing celecoxib by using a one-pot method. The method comprises the following steps: in the presence of ethidene diamine, mixing p-methylacetophenone and ethyltrifluoroacetate, and enabling the components to react completely at 40-80 DEG C without other solvent so as to obtain a reaction liquid of an intermediate DO; putting the reaction liquid into an alcohol solvent, further adding bihydrazino-benzsulfamide hydrochloride, further adding an organic acid to adjust the pH value to 3-6, controlling the temperature of a material liquid to 50-80 DEG C, andenabling the components to react completely; after the reaction is completed, adding water, cooling to 10-30 DEG C to separate out a crystal, and carrying out suction filtration so as to obtain a crude product of celecoxib; dissolving the crude product with methanol, dropping the material liquid into water, controlling the temperature of the material liquid to 40-50 DEG C in the dropping process,cooling to 10-30 DEG C to separate out a crystal after dropping is completed, and carrying out suction filtration, thereby obtaining a finished product of celecoxib. The total yield of the product prepared by using the method is greater than 85%, and HPLC (High Performance Liquid Chromatography) tests show that the purity of the product is greater than or equal to 99.90%.