35999-53-2

Basic information

• Product Name: 4,4,4-trifluoro-1-(4-nitrophenyl)butane-1,3-dione
• Synonyms: 4,4,4-trifluoro-1-(4-nitrophenyl)butane-1,3-dione;4,4,4-TRIFLUORO-1-(4-NITROPHENYL)-1,3-BUTANEDIONE;1,3-Butanedione, 4,4,4-trifluoro-1-(4-nitrophenyl)-;4,4,4-Trifluoro-1-(4-Nitrophenyl)-1,3-Butanedione(WXC04299)
• CAS NO: 35999-53-2
• Molecular Formula: C₁₀H₆F₃NO₄
• Molecular Weight: 261.154
• Mol File: 35999-53-2.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4,4,4-trifluoro-1-(4-nitrophenyl)butane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,4-trifluoro-1-(4-nitrophenyl)butane-1,3-dione(35999-53-2)
• EPA Substance Registry System: 4,4,4-trifluoro-1-(4-nitrophenyl)butane-1,3-dione(35999-53-2)

Safety Data

• Hazardous Substances Data: 35999-53-2(Hazardous Substances Data)

Usage

General Description

4,4,4-trifluoro-1-(4-nitrophenyl)butane-1,3-dione is a chemical compound that consists of a butane backbone with a 4-nitrophenyl group attached at the 1 position and a trifluoromethyl group attached at each of the 4 positions. It is a yellow crystalline solid that is used in the synthesis of pharmaceuticals and agrochemicals. 4,4,4-trifluoro-1-(4-nitrophenyl)butane-1,3-dione is known for its potential use as a herbicide due to its ability to inhibit the enzyme p-hydroxyphenylpyruvate dioxygenase. Its structural features make it an important building block in the development of various organic compounds and it is commonly used in research and industrial settings.

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 100-19-6 (4-nitrophenyl)ethanone 

Downstream Products

• 170571-05-8 4-[5-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide 
• 170569-98-9 4-[5-(4-aminophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide 
• 929606-74-6 C₁₆H₉BrF₃N₃O₂ 
• 303130-62-3 5-(4-nitrophenyl)-1-phenyl-3-trifluoromethylpyrazole 
• 99-77-4 ethyl 4-nitrobenzoate 

Relevant articles and documents

An Integrated Continuous Flow Micro-Total Ultrafast Process System (μ-TUFPS) for the Synthesis of Celecoxib and Other Cyclooxygenase Inhibitors

Integrated continuous manufacturing has emerged as a promising device for the rapid manufacturing of active pharmaceutical ingredients (APIs). We herein report a newly designed continuous flow micro-total process system platform for the rapid manufacturing of celecoxib, a selective nonsteroidal anti-inflammatory drug. This approach has been proven generally for the synthesis of several alkyl and aryl substituted pyrazoles. In order to minimize the tedious work-up process of potential reaction intermediates/products, we have developed a continuous flow extraction and separation platform to carry out the entire reaction sequence resulting in a short residence time with good yield. The present process was further extended to gram-scale synthesis of the COX-2-related API, viz. celecoxib, in the continuous flow process.

1,5-Diketones Synthesis via Three-Component Cascade Reaction

A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.

First synthesis of functionalized 5-aryl-3-(trifluoromethyl)phenols by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-aryl-3-silyloxy-1-trifluoromethyl-2-en-1-ones

A variety of functionalized 5-aryl-3-(trifluoromethyl)phenols were prepared by the first TiCl4-mediated [3+3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-aryl-3-trimethylsilyloxy-1-trifluoromethyl-2-en-1-ones.