622-61-7

Usage

Uses

Used in Fragrance and Flavoring Industry:
4-Chlorophenetole is used as a fragrance and flavoring agent for its sweet, floral scent, enhancing the sensory appeal of various consumer products.
Used in Perfumery:
In the production of perfumes, 4-chlorophenetole serves as a key ingredient that contributes to the overall aroma profile, providing a distinct and pleasant scent.
Used in Chemical Synthesis:
4-Chlorophenetole is utilized as a precursor in the synthesis of pharmaceuticals and agrochemicals, where its unique chemical structure is essential for creating specific compounds with desired properties.

InChI:InChI=1/C8H9ClO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2H2,1H3

Upstream product

• 473-29-0 N,N-Dichlorobenzenesulfonamide 
• 107-06-2 1,2-dichloro-ethane 
• 103-73-1 Phenetole 
• 297766-64-4 1,3-Diphenyltriazen 
• 68714-37-4 triethoxyacetonitrile 
• 106-48-9 4-chloro-phenol 
• 75-03-6 ethyl iodide 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 105-58-8 Diethyl carbonate 
• 64-17-5 ethanol 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 109-63-7 boron trifluoride diethyl etherate 
• 106-39-8 bromochlorobenzene 
• 141-52-6 sodium ethanolate 

Downstream Products

• 105475-33-0 4-(2-ethoxy-5-chloro-phenyl)-4-oxo-butyric acid 
• 156-43-4 4-Ethoxyaniline 
• 6178-89-8 5,5'-dichloro-2,2'-dihydroxybenzophenone 
• 108904-14-9 2-hydroxy-isophthalic acid mono-(4-chloro-phenyl ester) 
• 101571-55-5 2,2'-diethoxy-5,5'-dichloro-benzophenone 
• 1147105-68-7 2-(4-ethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 645-26-1 (4-ethoxyphenyl) phenyl sulfide 
• 928709-67-5 C₈H₈Cl₂O₃S 
• 103-73-1 Phenetole 
• 109514-48-9 2-hydroxy-isophthalic acid-(4-chloro-phenyl ester)-methyl ester 
• 106-48-9 4-chloro-phenol 
• 5392-86-9 2,4-dichloro-1-ethoxybenzene 
• 23399-88-4 2,4,6-trichlorophenyl ethyl ether 
• 83802-00-0 1,3,4,5,6-pentachloro-4-ethoxycyclohexene 

Relevant academic research and scientific papers

Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols

N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.

Efficient halogenation synthesis method of aryl halide

The invention discloses an efficient halogenation synthesis method of aryl halide. The method comprises the following step: in the presence of a catalyst (sulfoxide or oxynitride), a halogenation reagent and a solvent, carrying out a halogenation reaction on an aromatic ring compound to obtain the aryl halide. According to the present invention, in the presence of a catalyst (sulfoxide or nitrogenoxide), a halogenation reagent and a solvent, the aromatic ring is subjected to an efficient halogenation reaction, such that the very useful aryl halide can be obtained with high activity and high selectivity; and by adopting the method disclosed by the invention, aryl halides can be efficiently synthesized, and the method has a wide application prospect in actual production.

Electrophotocatalytic SNAr Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base

The electrophotocatalytic SNAr reaction of unactivated aryl fluorides at ambient temperature without strong base is demonstrated.

A new alkylation of aryl alcohols by boron trifluoride etherate

The ethylation of aryl alcohols by an ethyl moiety of boron trifluoride etherate is described. The reaction proceeded cleanly and afforded good yields of the corresponding aryl ethyl ethers. It tolerated the presence of functional groups such as aryl, alkyl, halogens, nitro, nitrile, and amino. However, the presence of amino or nitro groups ortho to a hydroxyl group of an aryl compound drastically reduced the yields of the anticipated products due to the chelation of the aforementioned functional groups with boron trifluoride etherate. A nitrogen atom in the aromatic ring system, as exemplified by hydroxypyridine and 8-hydroxyquinoline, completely inhibited the reaction. Resorcinol, hydroquinone, and aryl alcohols with aldehyde functions decomposed under the reaction conditions.

Selective Halogenation Using an Aniline Catalyst

Electrophilic halogenation is used to produce a wide variety of halogenated compounds. Previously reported methods have been developed mainly using a reagent-based approach. Unfortunately, a suitable "catalytic" process for halogen transfer reactions has yet to be achieved. In this study, arylamines have been found to generate an N-halo arylamine intermediate, which acts as a highly reactive but selective catalytic electrophilic halogen source. A wide variety of heteroaromatic and aromatic compounds are halogenated using commercially available N-halosuccinimides, for example, NCS, NBS, and NIS, with good to excellent yields and with very high selectivity. In the case of unactivated double bonds, allylic chlorides are obtained under chlorination conditions, whereas bromocyclization occurs for polyolefin. The reactivity of the catalyst can be tuned by varying the electronic properties of the arene moiety of catalyst.

Practical Ligand-Free Copper-Catalysed Short-Chain Alkoxylation of Unactivated Aryl Bromides

An efficient and practical short-chain alkoxylation of unactivated aryl bromides has been developed with special attention focussed on the applicability of the reaction. Sodium alkoxide is used as the nucleophile, and the corresponding alcohol as the solvent. The reaction requires neither precious metals nor organic ligands. It uses a catalytic system consisting of copper(I) bromide as a catalyst, the corresponding alkyl formate as a noncontaminating cocatalyst, and lithium chloride as an additive. A wide range of substrates and test cases highlight the synthetic utility of the approach. Considering the commercial accessibility and affordability of the feedstocks, this protocol shows promise as a new alternative for the sustainable preparation of aryl alkyl ethers.

Design and synthesis of new potassium channel activators derived from the ring opening of diazoxide: Study of their vasodilatory effect, stimulation of elastin synthesis and inhibitory effect on insulin release

Benzenesulfonylureas and benzenesulfonylthioureas, as well as benzenecarbonylureas and benzenecarbonylthioureas, were prepared and evaluated as myorelaxants on 30 mM KCl-precontracted rat aortic rings. The most active compounds were further examined as stimulators of elastin synthesis by vascular smooth muscle cells and as inhibitors of insulin release from pancreaticβ-cells. The drugs were also characterized for their effects on glycaemia in rats. Benzenesulfonylureas and benzenesulfonylthioureas did not display any myorelaxant activity on precontracted rat aortic rings. Such an effect could be attributed to their ionization at physiological pH. By contrast, almost all benzenecarbonylureas and benzenecarbonylthioureas displayed a myorelaxant activity, in particular the benzenecarbonylureas with an oxybenzyl group linked to the ortho position of the phenyl ring. The vasodilatory activity of the most active compounds was reduced when measured in the presence of 80 mM KCl or in the presence of 30 mM KCl and 10 μM glibenclamide. Such results suggested the involvement, at least in part, of KATP channels. Preservation of a vasodilatory activity in rat aortic rings without endothelium indicated that the site of action of such molecules was located on the vascular smooth muscle cells and not on the endothelial cells. Some of the most active compounds also stimulated elastin synthesis by vascular smooth muscle cells. Lastly, most of the active vasorelaxant drugs, except 15k and 15t at high concentrations, did not exhibit marked inhibitory effects on the insulin releasing process and on glycaemia, suggesting a relative tissue selectivity of some of these compounds for the vascular smooth muscle.

An efficient monochlorination of electron-rich aromatic compounds catalysed by ammonium iodide

An efficient monochlorination of electron-rich aromatic compounds is developed, with which a series of regioselective monochlorinated products are obtained in good yields. In the reaction, ammonium iodide is used as catalyst and m-chloroperbenzoic acid is used as the terminal oxidant. Ammonium iodide is first oxidised to hypoiodous acid by m-chloroperbenzoic acid. The in situ generated active iodine species then reacts with the aromatic compound to form the active hypervalent iodine intermediate in two steps and this reacts with lithium chloride to afford eventually the chlorinated compounds.

An efficient chlorination of aromatic compounds using a catalytic amount of iodobenzene

An efficient method was developed for chlorination of aromatic compounds with electron-donating groups using iodobenzene as the catalyst and m-chloroperbenzoic acid as the terminal oxidant in the presence of 4-methylbenzenesulfonic acid in THF at room temperature for 24 h, and a series of the monochlorinated compounds was obtained in good yields. In this protocol, the catalyst iodobenzene was first oxidized into the hypervalent iodine intermediate, which then treated with lithium chloride and finally reacted with aromatic compounds to form the chlorinated compounds.

Ionic liquids as reagent and reaction medium: Preparation of alkyl aryl ethers

Room temperature ionic liquid, [bmIm]OH, is used as a green recyclable reaction medium and reagent for the alkylation of phenols in excellent yields. The recovered ionic liquid was reused five to six times with consistent activity.