61343-87-1

Usage

Class of organic compounds

Phenylpropanoids and polyketides

Physical state

Colorless liquid

Odor

Mild, aromatic

Common uses

a. Fragrance ingredient in perfumes
b. Fragrance ingredient in soaps
c. Fragrance ingredient in cosmetics
d. Production of flavors and fragrances

Chemical structure

Contains a benzene ring with three methyl groups at positions 1, 3, and 5, and a phenoxy group at position 2

Industrial applications

Versatile compound with various potential uses

Safety concerns

May pose health and environmental hazards if not properly managed

InChI:InChI=1/C15H16O/c1-11-9-12(2)15(13(3)10-11)16-14-7-5-4-6-8-14/h4-10H,1-3H3

Upstream product

• 108-95-2 phenol 
• 4028-63-1 iodomesitylene 
• 1194059-81-8 2-[(2,4,6-trimethylphenyl)iodonio]benzenesulfonate 
• 591-50-4 iodobenzene 
• 527-60-6 Mesitol 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 108-86-1 bromobenzene 

Downstream Products

• 151508-90-6 2-(2-Cyclopent-1-enyl-phenoxy)-1,3,5-trimethyl-benzene 

Relevant academic research and scientific papers

Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers

Herein, we describe a synthetic approach for arylation that exploits the in situ formation and reaction of an unsymmetrical diaryliodonium salt. In this way, aryl iodides are used as reagents in a metal-free reaction with phenols, and a trimethoxyphenyl (TMP) group is used as a “dummy” group to facilitate transfer of a wide range of aryl moieties. The scope of aryl electrophiles and phenol nucleophiles is broad (>30 examples) and the yields are high (52–95%, 80% avg.). One-pot coupling reactions avoid the synthesis of diaryliodonium salts and provide opportunities for sequential reactions and novel chemoselectivity. (Figure presented.).

CuI-USY as a Ligand-Free and Recyclable Catalytic System for the Ullmann-Type Diaryl Ether Synthesis

The catalytic potential of copper(I)-exchanged zeolites was evaluated in the Ullmann-type synthesis of diaryl ethers. Among four investigated zeolites (i.e., USY, MOR, β, and ZSM5), CuI-USY was the best catalyst and proved efficient under ligand-free conditions in toluene at 120 °C. CuI-USY was also easy to recover and was recyclable up to five times without significant loss of activity.

Preparation and X-ray structures of 2-[(aryl)iodonio]benzenesulfonates: novel diaryliodonium betaines

Herein we present a concise preparation and characterization of 2-[(aryl)iodonio]benzenesulfonates. Determination of the X-ray crystal structure reveals a distorted trigonal bipyramidal molecular geometry about iodine and a pseudo-square geometry within t

Cu-nanoparticle catalyzed O-arylation of phenols with aryl halides via Ullmann coupling

Recyclable Cu-nanoparticles provide an efficient, economic, and novel method for the synthesis of diaryl ethers via Ullmann type coupling. This method provides a wide range of substrate applicability and avoids the use of a heavy metal co-catalyst and gives diaryl ethers in satisfactory yields.

Facile N-arylation of amines and sulfonamides and O-arylation of phenols and arenecarboxylic acids

An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl inflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.

Oxidative dearomatization of phenols and anilines via λ3 - and λ5-iodane-mediated phenylation and oxygenation

Treatment of 2-methylphenols with chloro(diphenyl)-λ3- iodane led to their regioselective dearomatizing 2-phenylation into cyclohexa-2,4-dienone derivatives via a proposed ligand coupling reaction. In the same vein of investigation, treatment of 2-methylanilines with the λ5-iodane 2-iodoxybenzoic acid IBX reagent led to their regioselective dearomatization into previously undescribed ortho-quinol imines.

Regioselective hypervalent-iodine(III)-mediated dearomatizing phenylation of phenols through direct ligand coupling

(Chemical Equation Presented) Dearomatization: Treatment of phenols and naphthols substituted at the ortho position by a small electron-donating group D with chlorodiphenyl-λ3-iodane leads to their regioselective ortho phenylation to give cyclohexa-2,4-dienone derivatives (see scheme). The mechanism of this reaction involves a nonradical direct coupling of the ligands.

Facile O-Arylation of Phenols and Carboxylic Acids

(Equation presented) A facile, transition-metal-free O-arylation procedure for phenols and aromatic carboxylic acids has been developed that affords good to excellent yields of arylated products under very mild reaction conditions. A methoxy-substituted aryl triflate affords O-arylated products in high yields with excellent regioselectivity. This chemistry tolerates a variety of functional groups.

The photorearrangement of o-vinyl diaryl ethers into o-hydroxy stilbenes. Evidence against dipolar intermediates

On irradiation of the o-vinyl diaryl ethers 4, 7, and the D-labeled derivative 16, a rearrangement takes place leading to the phenol 6 (from 4) and the corresponding vinyl-bridged hydroxy stilbenes 8/17 (from 7/16) as primary products. The latter compound