Phenolate

Base Information

• Chemical Name: Phenolate
• CAS No.: 3229-70-7
• Molecular Formula: C6H5 O
• Molecular Weight: 93.1051
• DSSTox Substance ID: DTXSID70954086
• Nikkaji Number: J1.968.978F,J312.417G
• Wikidata: Q27122100
• Mol file: 3229-70-7.mol

Synonyms:phenol ion;phenoxy ion;phenoxy radical;phenoxyl radical

Chemical Property of Phenolate

Chemical Property:

• Vapor Pressure: 0.614mmHg at 25°C
• Boiling Point: 181.8°Cat760mmHg
• Flash Point: 72.5°C
• PSA: 23.06000
• Density: g/cm³
• LogP: 1.83040
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 93.034039779
• Heavy Atom Count: 7
• Complexity: 46.1

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[O-]
• General Description: The phenoxy radical (also referred to as phenolate, phenoxide, or related terms) is a reactive species derived from phenol through deprotonation, forming an anionic or radical intermediate. In catalytic and synthetic applications, phenoxides act as nucleophiles, participating in reactions such as allylic substitutions or aromatic nitro group displacements. Their reactivity is influenced by steric and electronic factors, as demonstrated in studies where phenoxides form diphenyl ethers via nucleophilic aromatic substitution or undergo enantioselective allylation when paired with optimized iridium catalysts. These findings underscore the versatility of phenoxides in organic synthesis, particularly in constructing complex ethers and pharmaceuticals.

Technology Process of Phenolate

There total 106 articles about Phenolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

phenoxy radical (2122-46-5,55748-05-5) + chlorite (14998-27-7) → chlorine dioxide (10049-04-4,25052-55-5) + phenolate (3229-70-7,42428-36-4)

Guidance literature:

In water; Rate constant; Equilibrium constant; Irradiation;

Reference yield:

thiophenolate (13133-62-5) + (2-Isocyano-ethoxy)-benzene → cyanide(1-) (57-12-5) + vinyl phenyl ether (766-94-9) + phenolate (3229-70-7,42428-36-4) + (2-Isocyano-ethylsulfanyl)-benzene (3126-28-1)

Guidance literature:

With sodium ethanolate; Rate constant; Product distribution; multistep reaction, 1.) ethanol, 25 deg C; 2.) ethanol;

DOI:10.1021/ja00271a082

Reference yield:

E-O-phenyl-p-nitrobenzaldoxime (75735-28-3) → phenolate (3229-70-7,42428-36-4) + 4-nitrobenzonitrile (619-72-7)

Guidance literature:

With hydroxide; In water; dimethyl sulfoxide; at 25 ℃; Rate constant; Mechanism; further reagent;

DOI:10.1039/P29890000489

upstream raw materials:

piperidine

O-phenyl ethanethioate

morpholine

piperazine

Downstream raw materials:

n-butyl phenyl ether

4-formylphenoxide ion

Phenyl acetate

3-nitro-6-phenoxypyridine

Refernces

Effects of catalyst activation and ligand steric properties on the enantioselective allylation of amines and phenoxides

10.1021/ol050029d

The research investigates the impact of catalyst preactivation and ligand size on the yield, enantioselectivity, and regioselectivity of reactions involving amines and phenoxides with allylic carbonates using a metallacyclic iridium catalyst. The study aims to optimize the synthesis of allylic amines and ethers, which are valuable building blocks for pharmaceuticals and biologically active molecules. The researchers found that both preactivating the catalyst and altering the ligand's steric properties significantly improved the reaction outcomes. Specifically, the use of an activated catalyst containing a bis-naphthethylamino group and phosphoramidite ligands L1 and L2 led to high yields and high regio- and enantioselectivities for a broad range of allylic carbonates. The chemicals used in the process include [Ir(COD)Cl]2, phosphoramidite ligands L1 and L2, various amines, phenoxides, and allylic carbonates. The conclusions of the study highlight the importance of catalyst activation and ligand design in achieving efficient and selective catalytic reactions.

Displacement of an Aromatic Nitro Group using Phenoxides

10.1039/c39870001373

The study investigates a new method for preparing diphenyl ethers by displacing an aromatic nitro group with phenoxides. It involves using substituted nitrobenzenes (2a-d) and various phenoxides, including sodium phenoxide and 2,6-disubstituted phenoxides, in dry dimethyl sulphoxide at 90°C for 16 hours. The nitrobenzenes act as the substrates, while the phenoxides serve as nucleophiles to displace the nitro group, forming diphenyl ethers. The study highlights that this method is particularly effective for synthesizing hindered diphenyl ethers from weakly nucleophilic phenoxides. The results show that the yield of diphenyl ethers is affected by the reaction temperature and the specific phenoxide used. Additionally, the study provides insights into the reaction mechanism, suggesting a radical nature rather than an anionic nucleophilic displacement mechanism in certain cases.

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