Anisole
CAS No.:
100-66-3
M. Wt:
108.138
M. Fa:
C7H8O
InChI Key:
RDOXTESZEPMUJZ-UHFFFAOYSA-N
Appearance:
Colorless clear liquid
Names and Identifiers of Anisole
CAS Number |
100-66-3 |
|---|---|
EC Number |
202-876-1 |
MDL Number |
MFCD00008354 |
IUPAC Name |
anisole |
InChI |
InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3 |
InChIKey |
RDOXTESZEPMUJZ-UHFFFAOYSA-N |
Canonical SMILES |
COC1=CC=CC=C1 |
UNII |
B3W693GAZH |
UNSPSC Code |
12352100 |
UN Number |
2222 |
Physical and chemical properties of Anisole
Boiling Point |
155 °C |
|---|---|
BRN |
506892 |
Decomposition |
When heated to decomp, emits acrid fumes. |
Density |
0.990-0.993 |
Exact Mass |
108.057518 |
explosive limit |
0.34-6.3%(V) |
Flash Point |
52 °C o.c. |
Index of Refraction |
1.515-1.518 |
LogP |
2.11 |
Melting Point |
-37 °C |
Merck |
14,669 |
Molecular Formula |
C7H8O |
Molecular Weight |
108.138 |
Odor |
Spicy-sweet |
Odor Threshold |
0.057ppm |
PSA |
9.23000 |
Solubility |
soluble (in ethanol) |
Stability |
Stable. Flammable. Incompatible with strong oxidizing agents. |
Storage condition |
Store below +30°C. |
Vapour density |
Relative vapor density (air = 1): 3.7 |
Vapour Pressure |
Vapor pressure, kPa at 25 °C: 0.47 |
Water Solubility |
1.6 g/L (20 ºC) |
Solubility of Anisole
| Solvent Type | Dissolution Behavior | Temperature Effect | pH Effect |
|---|---|---|---|
| Water | Slightly soluble | Solubility slightly increases with temperature | Little effect under neutral conditions; extreme pH may promote hydrolysis |
| Ethanol | Freely soluble | Solubility increases with rising temperature | Minimal pH influence |
| Diethyl ether | Freely soluble | Solubility increases with temperature | pH effect not significant |
| Chloroform | Freely soluble | High solubility, slightly increases with temperature | Little affected by pH changes |
| Hydrocarbons (e.g., hexane) | Soluble | Higher temperature aids dissolution | No obvious pH effect |
| Acidic aqueous solution | Partial hydrolysis (under strongly acidic conditions) | High temperature promotes hydrolysis reaction | Strong acids (e.g., concentrated HCl, H₂SO₄) may cause decomposition |
| Basic aqueous solution | Stable | Stability unaffected by increasing temperature | Generally stable under strong alkaline conditions, no significant reaction occurs |
Routine testing items of Anisole
| Test Item | Common Testing Methods | Method Overview |
|---|---|---|
| Appearance | Visual Inspection | Observe whether the sample is a colorless transparent liquid, and check for turbidity, precipitate, or foreign matter. Suitable for preliminary quality assessment. |
| Color | Platinum-Cobalt Colorimetric Method (GB/T 3143) | Compare the color of the liquid sample with standard platinum-cobalt solutions to assess color intensity, indicating purity or degree of oxidation. |
| Content (Main Component) | Gas Chromatography (GC) | Use capillary columns (e.g., DB-5) with FID detector and internal or external standard method for quantitative determination of anisole content, offering high sensitivity and accuracy. |
| Impurity Analysis | Gas Chromatography-Mass Spectrometry (GC-MS) | Separate and identify organic impurities in anisole (e.g., phenol, methanol, benzene) for trace impurity detection and structural confirmation. |
| Water Content | Karl Fischer Titration | Utilize the quantitative reaction of iodine and sulfur dioxide in the presence of pyridine and methanol with water to precisely determine trace amounts of moisture in the sample. |
| Acid Value | Acid-Base Titration | Titrate free acids in the sample (e.g., acidic substances generated from oxidation of phenol) with standard sodium hydroxide solution, expressed as mg KOH/g. |
| Refractive Index | Refractometry (20°C) | Measure the refractive index of anisole at a specified temperature (n²⁰D ≈ 1.517–1.519) to aid in identification and purity assessment. |
| Boiling Point/Boiling Range | Distillation Method | Determine the boiling point range of anisole (approximately 153–155°C) to evaluate volatility and purity. |
| Density | Density Bottle Method or Digital Density Meter | Measure the mass per unit volume at a specified temperature (e.g., 20°C) to verify consistency of the substance (ρ ≈ 0.996 g/cm³). |
Safety Information of Anisole
Key Milestone of Anisole
| Time | Event | Description |
|---|---|---|
| 1830s | First Isolation and Naming | The compound was first isolated by the French chemist Auguste Cahours from anise oil (anise oil), and named "anisole" (methoxybenzene) due to its origin from anise. |
| 1840s–1850s | Preliminary Structural Determination | With the development of organic chemical structure theory (before Kekulé's benzene ring model), anisole was confirmed to be methoxybenzene, i.e., an aromatic ether with a methoxy group (–OCH₃) attached to the benzene ring. |
| 1870s | Synthesis Methods Established | Chemists developed the classic Williamson ether synthesis method for the preparation of anisole through the reaction of sodium phenoxide with methyl iodide (or dimethyl sulfate), enabling its artificial synthesis. |
| Late 19th century–early 20th century | Industrial Flavor Application | Due to its sweet anise-like fragrance, anisole was widely used as a flavoring agent in food, cosmetics, and perfumes. |
| 1930s–1940s | Establishment as an Organic Synthesis Intermediate | Anisole became an important aromatic intermediate in the synthesis of dyes, drugs, and pesticides due to the activating and directing effects of the methoxy group on the benzene ring (ortho/para-directing group). |
| 1950s–1970s | Expanded Applications in Medicinal Chemistry | The anisole structural unit was introduced into various drug molecules, such as local anesthetics, antihistamines, and estrogen analogs, to enhance efficacy or metabolic stability. |
| 1980s–present | Applications in Fine Chemicals and Materials Science | Used in the synthesis of liquid crystal materials, optoelectronic materials, and polymer monomers; also used as a standard reference in gas chromatography and mass spectrometry analysis. |
| 21st Century | Green Synthesis and Sustainable Research | Development of more environmentally friendly synthetic pathways for anisole (e.g., using solid acid catalysts, microwave-assisted reactions) to reduce waste emissions from traditional methods. |
Applications of Anisole
Anisole finds extensive applications across various industries:
- Fragrance Industry: It is used as a precursor for synthetic fragrances and flavorings due to its pleasant aroma.
- Pharmaceuticals: Anisole serves as an intermediate in the synthesis of various pharmaceutical compounds.
- Solvent: Its properties make it useful as a solvent in organic synthesis and extraction processes.
Interaction Studies of Anisole
Research has shown that anisole interacts with various electrophiles and can form complexes with metal carbonyls. For instance, anisole forms π-complexes with chromium carbonyls, indicating its potential utility in coordination chemistry. Studies have also explored its hydrolysis reactions under high-temperature conditions, which yield significant amounts of phenol.
Similar Compounds: Comparison with Other SimilarBiological Activity of Anisole
Anisole has been studied for its biological properties, including its role as a plant metabolite. Some derivatives of anisole are found in natural and artificial fragrances and may exhibit antimicrobial properties. Additionally, anisole and its derivatives have been investigated for their potential effects on human health, including toxicity assessments that indicate relatively low toxicity levels.
Physical sample testing spectrum (NMR) of Anisole
Cas:71-43-2
