2243-42-7

Basic information

• Product Name: 2-PHENOXYBENZOIC ACID
• Synonyms: LABOTEST-BB LT00455377;2-CARBOXY-DIPHENYL ETHER;2-PHENOXYBENZOIC ACID;RARECHEM AL BE 1507;O-PHENOXYBENZOIC ACID;2-phenoxy-benzoicaci;Benzoic acid, o-phenoxy-;ortho-Phenoxybenzoic acid
• CAS NO: 2243-42-7
• Molecular Formula: C₁₃H₁₀O₃
• Molecular Weight: 214.22
• EINECS: 218-811-5
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;C13 to C42+;Carbonyl Compounds;Carboxylic Acids
• Mol File: 2243-42-7.mol

Chemical Properties

• Melting Point: 110-112 °C(lit.)
• Boiling Point: 355 °C
• Flash Point: 132 °C
• Appearance: /
• Density: 1.1553
• Vapor Pressure: 2.73E-05mmHg at 25°C
• Refractive Index: 1.5090 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.53(at 25℃)
• BRN: 978452
• CAS DataBase Reference: 2-PHENOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENOXYBENZOIC ACID(2243-42-7)
• EPA Substance Registry System: 2-PHENOXYBENZOIC ACID(2243-42-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DH6293560
• TSCA: Yes
• Hazardous Substances Data: 2243-42-7(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
2-Phenoxybenzoic acid is used as an internal standard for the quantification of pyrethroid metabolites. It helps in improving the accuracy and precision of the analytical method by compensating for any variations in the sample preparation and instrumental analysis.

Purification Methods

Crystallise the acid from aqueous EtOH or H2O (m 114o). [Beilstein 10 H 65, 10 I 28, 10 II 40, 10 III 99, 10 IV 132.]

InChI:InChI=1/C13H10O3/c14-13(15)11-8-4-5-9-12(11)16-10-6-2-1-3-7-10/h1-9H,(H,14,15)/p-1

Upstream product

• 123-91-1 1,4-dioxane 
• 90-47-1 xanth-9-one 
• 865-47-4 potassium tert-butylate 
• 102-09-0 bis(phenyl) carbonate 
• 109-72-8 n-butyllithium 
• 101-84-8 diphenylether 
• 60-29-7 diethyl ether 
• 34883-46-0 1-(2-iodophenoxy)benzene 
• 3991-61-5 1-methyl-2-phenoxybenzene 
• 6476-32-0 o-phenoxybenzonitrile 
• 7120-45-8 phenyl (2-phenoxy)benzoate 
• 19434-34-5 2-(phenoxy)benzaldehyde 
• 118-55-8 phenyl Salicylate 
• 591-51-5 phenyllithium 

Downstream Products

• 349414-59-1 2-phenoxy-benzoic acid-(2-nitro-anilide) 
• 90-47-1 xanth-9-one 
• 140437-02-1 2-phenoxy-N-phenylbenzamide 
• 21905-56-6 methyl 2-phenoxybenzoate 
• 41755-76-4 ethyl 2-phenoxybenzoate 
• 6082-87-7 o-carboxyphenyl p-nitrophenyl ether 
• 601-99-0 2-hydroxy-6-nitrobenzoic acid 
• 384861-84-1 5-nitro-2-(4-nitro-phenoxy)-benzoic acid 
• 72084-13-0 2-phenoxybenzamide 
• 873986-45-9 2-(4-iodo-phenoxy)-benzoic acid 
• 65569-08-6 5-Chloro-N-(2-diethylamino-ethyl)-2-methoxy-4-(2-phenoxy-benzoylamino)-benzamide 
• 13807-84-6 (2-phenoxyphenyl)methanol 
• 31462-52-9 bis-(2-phenoxybenzyl) oxalate 
• 144463-64-9 allyl 2-phenoxybenzoate 

Relevant articles and documents

Synthesis and biological evaluation of disubstituted amidoxanthones as potential telomeric G-quadruplex DNA-binding and apoptosis-inducing agents

A series of disubstituted xanthones was obtained by cationic modification of xanthone's C2 and C7 with amine groups of different pKa values. Modified structures by using moieties with high pKa values had good antitumor activity according to the MTT assay, AO/EB staining and flow cytometry assay, especially bis-dimethylamine derivative (5a). Further study indicated that compound 5a had good binding activity to telomeric G-quadruplex DNA, as detected by using spectroscopy methods, melting profiles, polymerase chain reaction stop assay and molecular modeling study. The results suggested that the antitumor activity of 5a might be associated with its stabilization of G-quadruplex DNA, which could be developed as new G-quadruplex DNA stabilizer and potent antitumor agents.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

The present invention relates to a compound for an organic electronic element. To the present invention, an organic electronic element having high luminous efficiency, low driving voltage, and high heat resistance can be provided, and color purity and lifetime of the organic electronic element can be improved.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

The present invention provides a compound represented by chemical formula 1, an organic electric device including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device including the organic electric device. By including the compound represented by chemical formula 1 in the organic material layer, the driving voltage of the organic electric device can be lowered, luminous efficiency and lifespan can be improved, and in particular, the lifespan can be improved.COPYRIGHT KIPO 2021

Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation

A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.

Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution

Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.

Preparation method of xanthydrol

The invention relates to the chemical field, in particular to a preparation method of xanthydrol. The method comprises the steps as follows: 31.3 g of o-chlorobenzoic acid, 37.6 g of phenol, 5.53 g ofpotassium carbonate, 16.2 mL of pyridine, 2 g of copper powder, 2 g of cuprous iodide and 200 mL of water are added to a 500 mL three-neck flask, the mixture is stirred mechanically, subjected to reflux for 2 h and cooled to the room temperature, diluted hydrochloric acid is added to make a reaction solution to be acid, a solid is filtered out, washed and dissolved in a 10% sodium hydroxide aqueous solution, the obtained solution is added to a mixed solution of acetic acid and water for precipitation of a solid, the obtained solid is recrystallized with the mixed solution of acetic acid and water, and 36.4 g of white crystal o-phenoxybenzoic acid is obtained; 20 g of o-phenoxybenzoic acid and 80 mL of tetrahydrofuran are added to a 150 mL three-neck flask, the mixture is stirred mechanically and cooled to 0 DEG C, 23 mL of a catalyst is dropwise added at the temperature of 0 DEG C, the obtained mixture is heated for reflux for 30 min after addition and cooled to the room temperature,and ice water is added to a reaction solution. The technological process is simple and safe to operate, the production cost is reduced, environmental pollution is avoided in the reaction process, andthe product quality is improved.

Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis

We have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature. Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C?O bond cleavage, we developed a novel approach to the C?O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a one-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.

A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids

We report on the use of visible light photoredox catalysis for the radical Smiles rearrangement of 2-aryloxybenzoic acids to obtain aryl salicylates. The method is free of noble metals and operationally simple and the reaction can be run under mild batch or flow conditions. Being a redox neutral process, no stoichiometric oxidants or reductants are needed.

Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement

We report herein, a silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C-O or C-S bond cleavage. Aryl-2-mercaptobenzoates undergo oxidative dimerization through a thiol moiety in situ.

Copper-mediated direct aryloxylation of benzamides assisted by an N, O -bidentate directing group

Copper-mediated selective mono- or diaryloxylation of benzamides has been achieved by using 2-aminopyridine 1-oxide as a new and removable N,O-bidentate directing group. The reaction system shows a broad substrate scope and provides a straightforward way for the synthesis of mono- and diaryloxylated benzoic acids.