28165-72-2

Usage

Derived from

Phenol

Physical State

Clear, colorless liquid

Odor

Mildly pleasant

Uses

+ Disinfectant
+ Germicide
+ Fungicide
+ Industrial and agricultural applications
+ Production of pharmaceuticals, dyes, and perfumes

Importance

Intermediate in the synthesis of other organic compounds

Precautions

Harmful if ingested, inhaled, or absorbed through the skin

InChI:InChI=1/C8H6Br2O2/c1-5(11)12-8-6(9)3-2-4-7(8)10/h2-4H,1H3

Upstream product

• 608-33-3 2,6-dibromophenol 
• 108-24-7 acetic anhydride 
• 108-22-5 Isopropenyl acetate 
• 75-36-5 acetyl chloride 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 108-36-1 1,3-dibromobenzene 
• 108-95-2 phenol 

Downstream Products

• 2887-72-1 1-(3,5-dibromo-4-hydroxyphenyl)ethan-1-one 
• 1051969-85-7 1-(2-{2,6-bis[4-(pyridyl)phenylethynyl]phenoxy}ethyl)pyrrole-2,5-dione 
• 1383816-07-6 C₄₈H₃₆N₂O₆ 
• 1352646-01-5 4,4'-(5-(2-(2-(2-(2,6-bis((4-(pyridin-4-yl)phenyl)ethynyl)phenoxy)ethoxy)ethoxy)ethoxy)-1,3-phenylene)dipyridine 
• 1051969-83-5 2,6-bis((4-(pyridin-4-yl)phenyl)ethynyl)phenol 
• 1051969-81-3 2,6-bis((4-(pyridin-4-yl)phenyl)ethynyl)phenyl acetate 

Relevant academic research and scientific papers

Through-Space Polar-π Interactions in 2,6-Diarylthiophenols

Molecular recognition between polar groups and aromatic molecules is fundamentally important to rational drug design. Although it has been well established that many polar functionalities interact with electron-rich aromatic residues through energetically favorable polar-π interactions, there is a limited understanding of the association between thiols and aromatic systems. Herein we report physical-organic chemistry studies on 2,6-diarylthiophenols that possess the central thiophenol ring and two flanking aromatic rings with tunable electronic properties caused by substituents at distant para position. Hammett analysis revealed that pKa values and proton affinities correlate well with Hammett sigma values of substituents. Additional energy decomposition analysis supported the conclusion that both through-space SH-π interactions and S?-π interactions contribute to intramolecular stabilization of 2,6-diarylthiophenols.

Probing Through-Space Polar-π Interactions in 2,6-Diarylphenols

Although it is well established that the acidity of phenol can be fine-tuned with substituents on its aromatic ring via through-bond effects, the role of through-space effects on the acidity of phenols is presently poorly understood. Here, we present integrated experimental and computational studies on substituted 2,6-diarylphenols that demonstrate the essential contribution from through-space OH -π interactions and O--π interactions in the observed trends in proton affinities and acidities of 2,6-diarylphenols.

Ligand-Promoted Palladium-Catalyzed C?H Acetoxylation of Simple Arenes

The palladium-catalyzed C?H oxidation of simple arenes is an attractive strategy to obtain phenols, which have many applications in the fine chemicals industry. Although some advances have been made in this research area, low reactivity and selectivity are, in general, observed. This report describes a new catalytic system for the efficient C?H acetoxylation of simple arenes based on Pd(OAc)2 and a pyridinecarboxylic acid ligand.

O-acylation of substituted phenols with various alkanoyl chlorides under phase-transfer catalyst conditions

Esterification of several types of mono-and disubstituted phenols with various mono-and dialkanoyl chlorides was performed in phase-transfer catalysis conditions, using tetrabutylammonium chloride in a mixture of aqueous NaOH and dichloromethane. The process is particularly efficient (almost quantitative yields) as well as rapid (only 5 min reaction time, at a temperature of0°C). Taylor & Francis Group, LLC.

Synthesis of a bridging ligand with a non-denatured protein pendant: Toward protein encapsulation in a coordination cage

Toward protein encapsulation by a synthetic host, we synthesized an ubiquitin-dangled ligand, a potential precursor of a nanoscale coordination cage. The key step is the addition of a C-terminal Cys76 SH group, which was introduced by Gly76Cys mutation, to a maleimide acceptor on the ligand. The C-terminal mutation and the SH addition to the ligand did not damage the ubiquitin moiety at all, neither structurally nor conformationally.

Dye molecules for simple co-sensitization process: Fabrication of mixed-dye-sensitized solar cells

Sensitive kind of dye: Co-sensitization of the TiO2 electrode using PcS15 and the dye D131 results in a dramatic enhancement of the photocurrent response for the entire visible-light region. This method provides a simple design for accessing dye-sensitized solar cells. Copyright

Endohedral peptide lining of a self-assembled molecular sphere to generate chirality-confined hollows

At the interior of a ca. 5 nm-sized self-assembled coordination sphere, 24 amino acids (or peptides) are lined to generate chirality-confined protein-mimic cavities, whose structures are well-characterized by spectroscopy and X-ray analysis. Copyright

Antioxidant building blocks I. The unexpected C-acetylation of 2,6-Di-tert-butylphenol with isopropenyl acetate

While the reaction of some 2-substituted and 2,6-disubstituted phenols with isopropenyl acetate resulted in the corresponding phenol acetates, in the reaction of 2,6-di-tert-butylphenol, a useful starting material of antioxidant building blocks, under the same conditions 4-acetyl-2,6-di-tert-butylphenol was the only product.