Potassium phenoxide
CAS No.:
100-67-4
M. Wt:
132.202
M. Fa:
C6H5KO
InChI Key:
ZGJADVGJIVEEGF-UHFFFAOYSA-M
Appearance:
Off-White To Pink Solid
Names and Identifiers of Potassium phenoxide
CAS Number |
100-67-4 |
|---|---|
EC Number |
202-877-7 |
MDL Number |
MFCD00036027 |
IUPAC Name |
potassium;phenoxide |
InChI |
InChI=1S/C6H6O.K/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1 |
InChIKey |
ZGJADVGJIVEEGF-UHFFFAOYSA-M |
Canonical SMILES |
C1=CC=C(C=C1)[O-].[K+] |
UNII |
9CQ00ODF3U |
UNSPSC Code |
12352100 |
Physical and chemical properties of Potassium phenoxide
Boiling Point |
181.8ºC at 760mmHg |
|---|---|
Exact Mass |
131.997742 |
Flash Point |
72.5ºC |
LogP |
1.83040 |
Melting Point |
103-104 °C |
Molecular Formula |
C6H5KO |
Molecular Weight |
132.202 |
PSA |
23.06000 |
Solubility |
DMSO (Slightly), Methanol (Slightly) |
Stability |
Hygroscopic |
Storage condition |
Hygroscopic, -20°C Freezer, Under inert atmosphere |
Vapour Pressure |
0.614mmHg at 25°C |
Solubility of Potassium phenoxide
| Solvent | Dissolution Behavior | Temperature Effect | pH Effect |
|---|---|---|---|
| Water | Soluble, forming a colorless transparent solution | Solubility increases with rising temperature | Stable under neutral to alkaline conditions; phenol precipitates under acidic conditions |
| Ethanol | Soluble, but solubility is lower than in water | Increasing temperature helps improve solubility | Less affected by pH, but may decompose in acidic ethanol |
| Diethyl ether | Slightly soluble or nearly insoluble | Minimal effect from temperature changes | Not applicable (diethyl ether is an aprotic solvent, where the concept of pH is not clearly defined) |
| Acetone | Soluble, though solubility is lower than in water | Solubility slightly increases with rising temperature | Unstable under acidic conditions, may release phenol |
| Benzene | Insoluble | Negligible dissolution; temperature effects are insignificant | No significant pH effect |
Safety Information of Potassium phenoxide
Key Milestone of Potassium phenoxide
| Year | Event/Milestone | Description |
|---|---|---|
| 1834 | Isolation of Phenol | German chemist Friedlieb Ferdinand Runge isolated phenol (carbolic acid) from coal tar, laying the foundation for further research on phenol derivatives, including potassium phenoxide. |
| 1842 | Preliminary Study of Phenol Structure | French chemist Auguste Laurent determined the chemical structure of phenol, promoting the synthesis and study of its salts (such as sodium and potassium salts). |
| Mid-19th Century | Establishment of Preparation Methods for Alkali Metal Phenoxides | Chemists prepared potassium phenoxide by reacting phenol with potassium hydroxide: C₆H₅OH + KOH → C₆H₅OK + H₂O, becoming a standard method in laboratory practice. |
| 1870s–1880s | Development of Kolbe-Schmitt Reaction | Sodium phenoxide was used to prepare salicylic acid, while potassium phenoxide also showed activity in similar carboxylation reactions, expanding its potential applications in organic synthesis. |
| Early 20th Century | Application as a Strong Nucleophile | Potassium phenoxide, due to its stronger nucleophilicity compared to phenol, was used as an alkylating precursor in reactions such as Williamson ether synthesis to synthesize aromatic ethers. |
| 1930s–1950s | Indirect Application in Drug and Dye Synthesis | Potassium phenoxide served as an intermediate in the construction of various aromatic compounds, such as in the synthetic pathways of antimalarial drugs and dyes (e.g., phenolphthalein indicators). |
| 1960s–1980s | Research Driven by Organometallic Chemistry | With deeper studies on the behavior of oxygen anion ligands, potassium phenoxide was used as a model compound to investigate metal-oxygen bond properties and reaction mechanisms. |
| 1990s to Present | Exploration in Green Chemistry and Catalyst Design | Potassium phenoxide has been studied as a basic promoter or co-catalyst in heterogeneous catalysis and phase-transfer catalysis, particularly showing potential value in C–O and C–C bond-forming reactions. |
| Early 21st Century | Experimental Applications in Materials Science | Its application in functional materials (e.g., polymer precursors, coordination polymers) was explored; however, it has not yet been widely industrialized. |
Applications of Potassium phenoxide
Potassium phenoxide has several applications:
- Organic Synthesis: It serves as a key reagent in synthesizing various organic compounds, including pharmaceuticals and agrochemicals.
- Catalysis: Its role as a base in catalyzed reactions makes it valuable in chemical manufacturing processes.
- Research: Used extensively in laboratories for studying reaction mechanisms and developing new synthetic methodologies.
Biological Activity of Potassium phenoxide
Potassium phenoxide exhibits various biological activities:
- Antimicrobial Properties: Some studies suggest that potassium phenoxide may possess antimicrobial effects, making it a candidate for use in pharmaceuticals and disinfectants.
- Enzyme Inhibition: Research indicates that it can inhibit certain enzymes, potentially affecting metabolic pathways.
Physical sample testing spectrum (NMR) of Potassium phenoxide
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