4237-44-9

Usage

Uses

Used in Fragrance Industry:
o-(1-Phenylethyl)phenol is used as a fragrance ingredient for its floral scent, contributing to the creation of various perfumes and other cosmetic products. Its pleasant aroma enhances the sensory experience of these products, making them more appealing to consumers.
Used in Food Industry:
In the food industry, o-(1-Phenylethyl)phenol serves as a flavoring agent, adding unique taste profiles to food products. Its ability to impart flavor without imparting color makes it a valuable addition to the formulations of various food items.
Used in Industrial Applications:
o-(1-Phenylethyl)phenol is utilized as an antimicrobial agent in some industrial applications. Its properties help to prevent the growth of microorganisms, ensuring the safety and longevity of certain products, particularly in environments where microbial contamination could be a concern.
It is important to handle and store o-(1-Phenylethyl)phenol with standard safety precautions to ensure its effectiveness and safety in these applications.

InChI:InChI=1S/C14H14O/c1-11(12-7-3-2-4-8-12)13-9-5-6-10-14(13)15/h2-11,15H,1H3

Upstream product

• 60492-39-9 2-(1-phenylethyl)anisole 
• 120346-43-2 1-(4-hydroxyphenyl)-1-phenylethane 
• 139-02-6 sodium phenoxide 
• 585-71-7 (1-bromoethyl)benzne 
• 100-42-5 styrene 
• 108-95-2 phenol 
• 38731-93-0 9-methyl-9H-xanthene 
• 3205-18-3 (S)-sec-phenethyl-3,5-dinitrobenzoate 
• 10034-85-2 hydrogen iodide 
• 7601-90-3 perchloric acid 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 676-58-4 methylmagnesium chloride 
• 346433-42-9 carbonic acid tert-butyl ester 2-formyl-phenyl ester 

Downstream Products

• 7615-22-7 2-[2-(1-phenyl-ethyl)-phenoxy]-ethanol 
• 79320-94-8 butyl-[2-(1-phenyl-ethyl)-phenyl]-ether 
• 70439-65-5 2,4-dichloro-6-(1-phenyl-ethyl)-phenol 
• 104307-28-0 [2-(1-phenyl-ethyl)-phenyl]-propyl ether 
• 120346-43-2 1-(4-hydroxyphenyl)-1-phenylethane 
• 343229-59-4 2-(4-bromobutoxy)diphenylmethylmethane 
• 62737-79-5 4-Cyclohexyl-2-(1-phenyl-ethyl)-phenol 
• 2769-94-0 2,4-di-(α-methylbenzyl)phenol 
• 92549-07-0 2-hydroxy-3-(1-phenylethyl)benzaldehyde 
• 1009103-94-9 2-(1-phenylethyl)-4-tritylphenol 
• 92435-59-1 2-hydroxy-3-(1-phenylethyl)-5-chlorobenzaldehyde 
• 1582787-88-9 5-bromo-2-hydroxy-3-(1-phenylethyl)benzaldehyde 
• 1582788-01-9 2-{[4-(pent-4-enyloxy)phenylimino]methyl}-6-(1-phenylethyl)phenol 
• 1582788-04-2 2-{[4-(pent-4-enyloxy)phenylimino]methyl}-6-(1-phenylethyl)-4-chlorophenol 

Relevant academic research and scientific papers

Asymmetric alkylation of diphenylmethane derivatives using (-)-sparteine

Alkylation of 2-oxygenated diphenylmethane derivatives using sec-butyllithium and (-)-sparteine gave enantiomeric excesses of up to 60% with allyl bromide but alkylations with methyl electrophiles were poorly selective. When compounds with a free hydroxy in the 2-position were alkylated the selectivity was reversed.

A simple Lewis acid induced reaction of phenols with electrophiles: Synthesis of functionalized 4H-chromenes and ortho-benzylphenols

Lewis acid ZnCl2 promoted cyclization protocol to 4H-chromenes is accomplished, using readily available phenols and acetophenones as starting materials. Interestingly, the process is feasible under the solvent free environment. Synthesis of a variety of 4H-chromenes have been accomplished using this strategy. In addition, this concept is extended to the synthesis of ortho-benzylphenols by treating phenols either with styrenes or secondary benzylic alcohols.

HBF4- and AgBF4-Catalyzed ortho-Alkylation of Diarylamines and Phenols

A silver-tetrafluoroborate- or HBF4-catalyzed ortho-alkylation reaction of phenols and diarylamines with styrenes has been explored. A broad substrate scope is presented as well as mechanistic experiments and discussion.

New approach to the generation of aryldifluoroboranes–prospective acid catalysts of organic reactions

A new approach for preparation of aromatic and fluoroaromatic difluoroboranes via the interaction between corresponding aryltrifluoroborates and ionic liquids containing tetrachloroaluminate-anion and aluminum chloride has been developed. Catalytic properties of obtained aryldifluoroboranes have been investigated in model reactions of phenols alkylation. The dependence of catalytic properties on both the nature of solvent used and the type of substituents in the aromatic ring of difluoroborane has been established.[Figure presented]

Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes

A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.

Efficient catalyst for hydroarylation reaction of styrene with phenol to obtain high DSP selectivity in mild condition

Background: Technical mixture of styrenated phenols including mono-, di-, and tristyrenated phenol, has been commonly applied for industrial materials such as rubber or plastic stabilizer, antioxidant, and nonionic surfactant, etc. Among these styrenated phenols, di-styrenated phenol should be most effective as rubber and plastic stabilizers. Although a number of catalysts for the synthesis of styrenated phenols have been explored, researches on the synthesis of styrenated phenol generally have been focused on selective preparation of mono-styrenated phenol MSP, rather than distyrenated phenol DSP. In this paper, we have investigated the hydroarylation reaction of styrene with phenol to find the optimal catalyst, including single catalysts and mixed catalysts, to get high selectivity to DSP under mild reaction conditions. Method: Hydroarylation reactions of styrene with phenol using various single catalysts, such as inorganic acids, organic acids, Lewis acids, and metal salt catalysts, have been conducted. To optimize the reaction conditions, hydroarylation reactions of styrene with phenol employing InCl3 catalyst were carried out with a variety of styrene amount, catalyst amount, reaction time, and reaction temperature. Halogenpromoted hydroarylation reactions of styrene with phenol were investigated in the presence of NBS or I2 as a halogen source and a variety of metal halides as a Lewis acid catalyst. Br-promoted hydroarylation reactions of styrene with phenol were accomplished using InCl3 along with NBS under a variety of NBS amount and reaction temperature. To explore the scope of Br-promoted hydroarylation, the reactions of various styrene derivatives with phenol were carried out using NBS and InCl3. Results: Hydroarylation reactions of styrene with phenol using various single catalysts, such as inorganic acids, organic acids, Lewis acids, and metal salt catalysts, have been conducted. Among 19 catalysts used, best results in both high conversion of phenol and high DSP selectivity are obtained with InCl3 catalyst. Using InCl3, total yield of styrenated phenols is 98% and product selectivity MSP/DSP/ TSP is 20/65/13. When InCl3 as an optimal catalyst was applied for the hydroarylation reactions of styrene with phenol under various reaction conditions, the optimal reaction conditions for obtaining a high yield, high DSP, and low MSP are as follows: styrene/phenol = 2 molar ratio, catalyst/phenol = 0.1 molar ratio, reaction time 6 hours, reaction temperature 120°C. In the halogen-promoted hydroarylation reactions of styrene with phenol in the presence of NBS or I2 as a halogen source and various metal halides as a Lewis acid catalyst, best yield (99%) and DSP selectivity (MSP/DSP/ TSP=13/42/41) were obtained using NBS and InCl3. The optimal reaction condition for Br-promoted hydroarylation reaction was found to be phenol 1 eq., styrene 2 eq., InCl3 0.04 eq., NBS 1 eq., 4 hours reaction time, room temperature. For the reactions of various styrene derivatives with phenol using NBS and InCl3, the best DSP selectivity was observed for the CH3-substituted styrene derivative. Conclusion: We have developed hydroarylation reaction of styrene with phenol for obtaining a high yield and a high DSP selectivity even at room temperature. Using NBS as a Br source and InCl3 as a catalyst at room temperature, Br-promoted hydroarylation reaction of styrene with phenol yields good results with respect to both yield and DSP selectivity.

METHOD OF PREPARING FOR SELECTIVE DI-STYRENATED PHENOL USING ZIRCONIUM OXIDE SOLID ACID CATALYST MANUFACTURED BY BEING IMPREGNATED ZIRCONIUM HYDROXIDE IN SULFURIC ACID AQUEOUS SOLUTION

The present invention relates to a selective preparation method of di-styrenated phenol represented by chemical formula 1 obtained by making a phenol compound represented by chemical formula 2 react with a styrene monomer in the presence of a zirconium oxide solid acid catalyst prepared by impregnating zirconium hydroxide with an aqueous sulfuric acid solution. In chemical formulas 1 and 2, R_1 and R_2 are each independently selected from hydrogen, a C_1-C_20 alkyl group, a C_1-C_20 alkoxyl group, a C_3-C_30 cycloalkyl group, and a C_6-C_30 aryl group. The selective preparation method according to the present invention can minimize the amount of an unreacted residual material and can dramatically increase selectivity of di-styrenated phenol by exhibiting a high reactivity in the presence of the zirconium oxide solid acid catalyst prepared by impregnating zirconium hydroxide with the aqueous sulfuric acid solution.COPYRIGHT KIPO 2018

Enantiospecific sp2–sp3 Coupling of ortho- and para-Phenols with Secondary and Tertiary Boronic Esters

The coupling of ortho- and para-phenols with secondary and tertiary boronic esters has been explored. In the case of para-substituted phenols, after reaction of a dilithio phenolate species with a boronic ester, treatment with Ph3BiF2 or Martin's sulfurane gave the coupled product with complete enantiospecificity. The methodology was applied to the synthesis of the broad spectrum antibacterial natural product (?)-4-(1,5-dimethylhex-4-enyl)-2-methyl phenol. For ortho-substituted phenols, initial incorporation of a benzotriazole on the phenol oxygen atom was required. Subsequent ortho-lithiation and borylation gave the coupled product, again with complete stereospecificity.

METHOD OF PREPARING FOR SELECTIVE DI-STYRENATED PHENOL USING TITANIUM DIOXIDE SOLID ACID CATALYST

The present invention relates to a method for producing di-styrenated phenol. More specifically, the present invention relates to a method for selectively producing di-styrenated phenol at high yield using solid titanium dioxide acid catalyst. According to the present invention, since the method for producing di-styrenated phenol ensures high reactivity in the presence of solid titanium dioxide acid catalyst, the method for producing di-styrenated phenol can minimize an amount of unreacted residues while remarkably increasing selectivity of di-styrenated phenol.(AA) Titanium dioxide (Powder form, 20 g)(BB) Titanium dioxide + Sulfuric acid + Distilled water (500 ml)(CC) Stir (Room temperature and 3 hours)(DD) Dry (110anddeg;C, and 12 hours)(EE) Sintering (600anddeg;C, 2 hours, and air atmosphere)(FF) Titanium dioxide solid acid catalyst (SO_4^2-/TiO_2) (Sulfuric acid : 5 wt%)COPYRIGHT KIPO 2017

METHOD FOR MANUFACTURING STYRENATED PHENOL

The present invention relates to a method for producing styrenated phenol which is represented by chemical formula 1. According to an embodiment of the present invention, provided is a method for producing styrenated phenol, which comprises the following steps: a step (a) for carrying out a reaction between a phenol compound and a styrene compound in the presence of a first acid catalyst; and a step (b) for carrying out a reaction after additionally inserting a styrene compound into a product obtained in the step (A) in the presence of a second acid catalyst. In the chemical formula 1, n refers to an integer of 1-3.COPYRIGHT KIPO 2017