6302-55-2

Basic information

• Product Name: 1-(4-Chlorophenyl)1,3-butanedione
• Synonyms: 1-(4-Chlorophenyl)1,3-butanedione;1-(4-Chlorophenyl)butane-1,3-dione, 4'-Chloro-3-oxobutyrophenone;4-Chlorobenzoylacetone
• CAS NO: 6302-55-2
• Molecular Formula: C₁₀H₉ClO₂
• Molecular Weight: 196.64
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 6302-55-2.mol
• Article Data: 28

Chemical Properties

• Melting Point: 73-74 °C
• Boiling Point: 312 °C at 760 mmHg
• Flash Point: 131.1 °C
• Appearance: /
• Density: 1.205 g/cm³
• Vapor Pressure: 0.000544mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.41±0.10(Predicted)
• CAS DataBase Reference: 1-(4-Chlorophenyl)1,3-butanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Chlorophenyl)1,3-butanedione(6302-55-2)
• EPA Substance Registry System: 1-(4-Chlorophenyl)1,3-butanedione(6302-55-2)

Safety Data

• Hazardous Substances Data: 6302-55-2(Hazardous Substances Data)

Usage

General Description

1-(4-Chlorophenyl)1,3-butanedione, also known as chlorphenylbutanone, is an organic compound with the chemical formula C10H11ClO2. It is a yellow to brownish liquid that is commonly used in the synthesis of pharmaceuticals and as a fragrance and flavoring agent. The compound is derived from the condensation of 4-chloroacetophenone and ethyl acetoacetate and is commonly used to impart a buttery and creamy flavor to products such as baked goods, candies, and dairy products. 1-(4-Chlorophenyl)1,3-butanedione is also known to exhibit antimicrobial properties, making it an effective preservative in various consumer products. However, it is important to note that the compound has been restricted for use in food production in some countries due to potential health concerns.

InChI:InChI=1/C10H9ClO2/c1-7(12)6-10(13)8-2-4-9(11)5-3-8/h2-5H,6H2,1H3

Upstream product

• 106-39-8 bromochlorobenzene 
• 165684-80-0 3-(4-chlorobenzoyl)pentane-2,4-dione 
• 153395-93-8 (+/-)-4-(4-chlorophenyl)but-3-yn-2-ol 
• 637-87-6 1-Chloro-4-iodobenzene 
• 79-20-9 acetic acid methyl ester 
• 99-91-2 para-chloroacetophenone 
• 67-64-1 acetone 
• 201230-82-2 carbon monoxide 
• 67864-02-2 4′-chloro-1-phenylbut-2-en-1-one 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 13014-48-7 4-chlorobenzoyl cyanide 
• 43053-63-0 6-(4-chlorophenyl)-4-hydroxy-2H-pyran-2-one 
• 141-78-6 ethyl acetate 
• 108-24-7 acetic anhydride 

Downstream Products

• 95346-57-9 C₁₆H₁₁ClN₃O₈^(1-) 
• 76387-95-6 6-(4-Chloro-phenyl)-4-methyl-1-phenyl-1H-pyrimidin-2-one 
• 76387-90-1 4-(p-chlorophenyl)-6-methyl-1-phenyl-2(1H)-pyrimidinone 
• 117184-81-3 1-(4-Chloro-phenyl)-2-(2-methyl-[1,3]dithiolan-2-yl)-ethanone 
• 76387-93-4 6-(4-Chloro-phenyl)-4-methyl-1-phenyl-1H-pyrimidine-2-thione 
• 135126-91-9 ethyl-5-methyl-4-(4-chlorophenyl)-isoxazole-3-carboxylate 
• 526220-86-0 (4-chloro-phenyl)-(7-ethoxy-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 135126-70-4 4-(4-chlorophenyl)-3,6-dimethylisoxazolo<3,4-d>pyridazin-7(6H)-one 
• 194856-46-7 5-Acetyl-6-(4-chloro-phenyl)-2-methyl-4-methylsulfanyl-2H-pyridazin-3-one 
• 194856-50-3 5-Acetyl-6-(4-chloro-phenyl)-4-methanesulfinyl-2-methyl-2H-pyridazin-3-one 
• 194856-30-9 5-Acetyl-6-(4-chloro-phenyl)-2-methyl-4-nitro-2H-pyridazin-3-one 
• 1032739-04-0 C₁₅H₁₈ClNO₂S₂ 
• 51439-55-5 3,4-bis(4-chlorobenzoyl)hexane-2,5-dione 
• 1228180-68-4 ethyl-2,3-bis(4-chlorobenzoyl)-4-oxopentanoate 

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.).

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