143771-04-4

Basic information

• Product Name: 2,4-Cyclohexadien-1-one, 4-(1,1-dimethylethyl)-6,6-difluoro-
• CAS NO: 143771-04-4
• Molecular Formula: C10H12F2O
• Molecular Weight: 186.201
• Mol File: 143771-04-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,4-Cyclohexadien-1-one, 4-(1,1-dimethylethyl)-6,6-difluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Cyclohexadien-1-one, 4-(1,1-dimethylethyl)-6,6-difluoro-(143771-04-4)
• EPA Substance Registry System: 2,4-Cyclohexadien-1-one, 4-(1,1-dimethylethyl)-6,6-difluoro-(143771-04-4)

Safety Data

• Hazardous Substances Data: 143771-04-4(Hazardous Substances Data)

Usage

General Description

2,4-Cyclohexadien-1-one, 4-(1,1-dimethylethyl)-6,6-difluoro- is a chemical compound with the molecular formula C10H12F2O. It is a derivative of cyclohexadienone, containing two fluorine atoms and a tert-butyl group. 2,4-Cyclohexadien-1-one, 4-(1,1-dimethylethyl)-6,6-difluoro- is often used as a building block in organic synthesis and can be used to create other fluorinated compounds. It is known for its strong aromatic odor and is considered to be a potentially hazardous chemical if not handled and disposed of properly. Additionally, it has potential applications in the pharmaceutical and agrochemical industries due to its unique structure and properties.

Upstream product

• 14366-60-0 1-(tert-butyl)-4-isopropoxybenzene 
• 98-29-3 4-tert-Butylcatechol 
• 1129-21-1 4-t-butyl-1,2-benzoquinone 
• 98-54-4 para-tert-butylphenol 
• 38946-63-3 2-fluoro-4-(1,1-dimethylethyl)phenol 

Relevant articles and documents

Fluorination of 4-alkyl-substituted phenols and aromatic ethers with fluoroxy and N-F reagents: Cesium fluoroxysulfate and N-fluoro-1,4-diazonia- bicyclo[2.2.2]octane dication salts case Dedicated to Prof. Dr. Boris ?emva in honor to his great contribution to fluorine chemistry.

4-Alkyl-substituted phenols and aromatic ethers were comparatively fluorinated with electrophilic fluorinating reagents such as cesium fluoroxysulfate (CFS), Selectfluor F-TEDA-BF4, and Accufluor NFTh in MeCN or MeOH. Reactions resulted in the formation of three types of products: 2-fluoro-4-alkyl-substituted corresponding compounds (5) as a result of ortho fluorination process, 4-alkyl-4-fluoro-cyclohexa-2,5- dienone compounds (6), resulting after an addition-elimination process, and 4-fluorosubstituted corresponding compounds (7) derived from ipso attack and release of the 4-alkyl group. The distribution of products depends on the bulkiness of alkyl groups at both positions and reaction media. The reaction in methanol proved more selective toward the formation of 2-fluoro derivatives. Tyramin and l-tyrozine were transformed with NFTh reagent in methanol to their fluorophenyl-substituted derivatives in good yield.

Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media

The transformations of organic molecules with F-TEDA-BF4 (1) were investigated in the hydrophilic ionic liquid (IL) 1-butyl-3-methyl- imidazolium tetrafluoroborate ([bmim][BF4], 2) and the hydrophobic IL 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6], 3). The range of substrates included alkyl substituted phenols 4a-c, 9, 13, 1,1-diphenylethene (15), alkyl aryl ketones 19-22, aldehydes 23-25 and methoxy-substituted benzene derivatives 26-30. The evaluation of the outcome of reactions performed in IL media in comparison to those of the corresponding reactions in conventional organic solvents revealed that the transformations in IL are less efficient and selective. The effect of the presence of a nucleophile (MeOH, H2O, MeCN) on the course of reaction was also studied.

The effect of heteroatoms on the reactions of organic molecules with caesium fluoroxysulphate

CsSO4F reacted at room temperature, or at 35°C in acetonitrile with various heteroatom-containing organic molecules, and three types of transformations have been observed. Fluoro substitution process took place with triphenylmethane, triphenylsilane, triphenylchlorosilane, 4-tert-butylphenol, benzaldehyde, and octanol, thus forming fluorotriphenylmethane, fluorotriphenylsilane, 2-fluoro-4-tert-butylphenol, benzoyl fluoride, or octanoyl fluoride in high yields. Substitution reaction was accompanied by fluoroaddition process in the case of 2-fluoro-4-tert-butylphenol, where 2,2-difluoro-4-tert-butylcyclohexadienon-4,6- was isolated. CsSO4F easily oxidised secondary alcohols to ketones, and 1,2-dihydro-4-tert-butylbenzene to quinone derivate. Oxygenation process was observed in the case of triphenylphosphine, and dibenzothiophene, while ethyl iodide was transformed to ethyliodo(III) difluoride. Solvent plays an important role in these reactions, being successfully performed in CH3CN, and completely inhibited in CH2Cl2, while different shapes of the effect on fluorination of various organic molecules were observed by altering solvent nature by successive mixing of CH3CN with CH2Cl2.