22272-48-6

Usage

Uses

Used in Perfume and Cosmetics Industry:
3-Benzylphenol is used as a fragrance ingredient for its pleasant aroma, enhancing the scent profiles of perfumes, soaps, and cosmetics.
Used in Pharmaceutical and Agrochemical Industries:
3-Benzylphenol serves as an intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used in Food and Beverage Industry:
3-Benzylphenol is used as a preservative in food and beverages to extend shelf life and maintain product quality.
However, it is important to note that exposure to high levels of 3-benzylphenol can be toxic and irritating to the skin and eyes, as well as harmful if ingested or inhaled. Therefore, proper handling and safety measures should be taken when working with this chemical to ensure the safety of both individuals and the environment.

InChI:InChI=1/C13H12O/c14-13-8-4-7-12(10-13)9-11-5-2-1-3-6-11/h1-8,10,14H,9H2

Upstream product

• 23450-27-3 m-benzylanisole 
• 7765-98-2 (3-hydroxyphenyl)(phenyl)methanol 
• 100-39-0 benzyl bromide 
• 108-95-2 phenol 
• 100-51-6 benzyl alcohol 
• 140-11-4 Benzyl acetate 
• 1711-05-3 m-anisoyl chloride 
• 100-83-4 meta-hydroxybenzaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 591-20-8 3-Bromophenol 
• 100-44-7 benzyl chloride 
• 108-43-0 3-monochlorophenol 
• 13020-57-0 3-hydroxybenzophenone 
• 496-64-0 3-hydroxy-2-pyrone 

Downstream Products

• 108-88-3 toluene 
• 108-95-2 phenol 
• 380363-94-0 1-benzyl-3-(3-chloropropoxy)benzene 
• 301221-12-5 trifluoro-methane sulfonic acid 3-benzyl-phenyl ester 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 1149748-50-4 C₁₈H₂₁BrO 
• 85838-94-4 N-Boc-1,2,3,6-tetrahydropyridine 
• 13020-57-0 3-hydroxybenzophenone 
• 1265585-69-0 C₂₃H₂₆O₃ 
• 1265585-51-0 C₂₂H₂₄O₃ 
• 80227-82-3 3-benzyl-2,6-dipropylanisole 
• 80227-97-0 3-benzyl-2,6-diallylanisole 
• 380364-08-9 3-[[[3-(3-benzylphenoxy)propyl](methyl)amino]methyl]phenol 
• 380363-98-4 1-benzyl-3-(3-iodopropoxy)benzene 

Relevant academic research and scientific papers

Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides

Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron-deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron-rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise-like energy profile. Notably, we isolated a rhodium η5-cyclohexadienyl complex intermediate with an sp3-hybridized carbon bearing both a nucleophile and a leaving group.

Insight into the chemoselective aromatic: Vs. side-chain hydroxylation of alkylaromatics with H2O2catalyzed by a non-heme imine-based iron complex

The oxidation of a series of alkylaromatic compounds with H2O2 catalyzed by an imine-based non-heme iron complex prepared in situ by reaction of 2-picolylaldehyde, 2-picolylamine, and Fe(OTf)2 in a 2?:?2?:?1 ratio leads to a marked chemoselectivity for aromatic ring hydroxylation over side-chain oxidation. This selectivity is herein investigated in detail. Side-chain/ring oxygenated product ratio was found to increase upon decreasing the bond dissociation energy (BDE) of the benzylic C-H bond in line with expectation. Evidence for competitive reactions leading either to aromatic hydroxylation via electrophilic aromatic substitution or side-chain oxidation via benzylic hydrogen atom abstraction, promoted by a metal-based oxidant, has been provided by kinetic isotope effect analysis. This journal is

Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H3PO3/I2

For the first time, H3PO3 was used as both the reducing reagent and the promotor in the reductive benzylation reactions with aryl aldehydes. By using a H3PO3/I2 combination, various aromatic aldehydes underwent iodination reactions and Friedel-Crafts type reactions with arenes via benzyl iodide intermediates, readily producing benzyl iodides and diarylmethanes in good yields. Intramolecular cyclization reactions also took place, giving the corresponding cyclic compounds. This new strategy features easy-handling, low-cost, and metal-free conditions.

Synthesis of Highly Substituted Phenols and Benzenes with Complete Regiochemical Control

Substituted phenols are requisite molecules for human health, agriculture, and diverse synthetic materials. We report a chemical synthesis of phenols, including penta-substituted phenols, that accommodates programmable substitution at any position. This method uses a one-step conversion of readily available hydroxypyrone and nitroalkene starting materials to give phenols with complete regiochemical control and in high chemical yield. Additionally, the phenols can be converted into highly and even fully substituted benzenes.

Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions

A novel metal-free process allowing the reductive desulfurization of various benzylic dithioketals to afford diarylmethane and benzylester derivatives with good to excellent yields is reported. At room temperature, this mild reduction process requires only the use of TMSCl and NaI in CH2Cl2 and tolerates a large variety of functional groups. (Figure presented.).

Au-Catalyzed Biaryl Coupling to Generate 5- To 9-Membered Rings: Turnover-Limiting Reductive Elimination versus ?-Complexation

The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates, via systematic modulation of the length of aryl-aryl linkage, but also the ability to arylate neutral and electron-poor arenes - substrates that do not react at all in the intermolecular process. Rendering the arylation intramolecular also results in phenomenologically simpler reaction kinetics, and overall these features have facilitated a detailed study of linear free energy relationships, kinetic isotope effects, and the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diaryl-gold(III) species. The turnover-limiting step for the formation of a series of fluorene derivatives is sensitive to the reactivity of the arene and changes from reductive elimination to ?-complexation for arenes bearing strongly electron-withdrawing substituents (σ > 0.43). Reductive elimination is accelerated by electron-donating substituents (ρ = -2.0) on one or both rings, with the individual σ-values being additive in nature. Longer and more flexible tethers between the two aryl rings result in faster reductive elimination from Ar-Au(X)-Ar and lead to the ?-complexation of the arene by Ar-AuX2 becoming the turnover-limiting step.

One-pot borylation/Suzuki-Miyaura sp2-sp3 cross-coupling

We describe the first one-pot borylation/Suzuki-Miyaura sp2-sp3 cross-coupling between readily available aryl (pseudo)halides and activated alkyl chlorides. This method streamlines the synthesis of diaryl methanes, α-aryl carbonyls and allyl aryl compounds, substructures that are commonly found in life changing drug molecules.

Preparation of functionalized organoindium reagents by means of magnesium insertion into organic halides in the presence of InCl3 at room temperature

Magnesium, indium, palladium: An efficient one-pot procedure for the direct preparation of triorganoindium reagents from organic halides by means of magnesium insertion in the presence of InCl3 and LiCl is reported (see scheme). The organoindium reagents are obtained in good yields from functionalized aryl, heteroaryl, and alkyl bromides and benzyl chlorides at 25 °C in THF within 4h. Moreover, the resulting organoindium reagents could be efficiently used as reagents in Pd-catalyzed cross-coupling reactions with a wide functional group tolerance. Copyright

Chemistry of photogenerated α-phenyl-substituted o-, m-, and p-quinone methides from phenol derivatives in aqueous solution

The enhanced photochemical reactivity of o-substituted phenols in its propensity to give o-quinone methide (o-QM) intermediates via excited state intramolecular proton transfer (ESIPT) was uncovered by Keith Yates as part of his now classic studies of photohydration of aromatic alkenes, alkynes, and related compounds. Photogeneration of QMs and the study of their chemistry along with potential biological applications are the focus of many groups. In this work, photochemical precursors to o-, m-, and p-QMs based on substituted phenols (hydroxybenzyl alcohols) and related compounds have been studied in aqueous solution as a function of pH and water content. The focus will be on QMs that are stabilized by an a-phenyl substituent, which enhances quantum yields for their formation, with the resulting QMs having longer lifetimes and easier to detect. Noteworthy is that all QM isomers can. be photogenerated with the o and m isomers being the most efficient, consistent with the Zimmerman "ortho-meta" effect. m-QMs have formal non-Kekule structures, and although they can be routinely photogenerated, are found to be most reactive. One m-QM was found, to undergo a photocondensation reaction at high pH giving rise to m-substituted oligomers. The mechanism, of QM formation in aqueous solution is believed to involve singlet excited phenols that undergo adiabatic deprotonation to give the corresponding photoexcited phenolate ion, which subsequently expels the hydroxide ion (photodehydroxylation). A pathway involving direct loss of water for the o-isomers is also possible in organic solvents.

HIV reverse transcriptase inhibitors

Compounds having the structure: are HIV reverse transcriptase inhibitors, wherein A, X, Y, Z, R1 and R2 are defined herein. The compounds and their pharmaceutically acceptable salts are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.