Crownethers
15-Crown-5
CAS: 33100-27-5
Molecular Formula: C10H20O5
Crownethers - Names and Identifiers
| Name | 15-Crown-5 |
| Synonyms | 15-Crown-5 Crownethers Lead ionophore V Crownpaleyellowliq 15-crown-5-ether 15-Crown-5 solution LABOTEST-BB LT00440921 Ethyleneoxidecyclicpentamer 1,4,10,13-Pentaoxacyclopentadecane 1,4,7,1,13-Pentaoxacyclopentadecane 1,4,7,10,13-Pentaoxacyclopentadecane 15-Crown-5,1,4,7,10,13-Pentaoxa-cyclo-pentadecane |
| CAS | 33100-27-5 |
| EINECS | 251-379-6 |
| InChI | InChI=1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2 |
Crownethers - Physico-chemical Properties
| Molecular Formula | C10H20O5 |
| Molar Mass | 220.26 |
| Density | 1.113 g/mL at 20 °C (lit.) |
| Melting Point | -20°C(lit.) |
| Boling Point | 93-96 °C/0.05 mmHg (lit.) |
| Flash Point | >230°F |
| Water Solubility | MISCIBLE |
| Solubility | Solubility in water: MISCIBLE |
| Vapor Presure | 0.5-0.82Pa at 20-25℃ |
| Appearance | Transparent liquid |
| Specific Gravity | 1.109 |
| Color | Clear colorless to light yellow |
| BRN | 1618144 |
| Storage Condition | room temp |
| Stability | Stable. Incompatible with oxidizing agents, strong acids. Avoid exposure to water or moist air. |
| Sensitive | Hygroscopic |
| Refractive Index | n20/D 1.465(lit.) |
| MDL | MFCD00005110 |
| Physical and Chemical Properties | Appearance of colorless liquid colorless or yellowish liquid, easy to moisture absorption, low toxicity, the eyes, respiratory system, skin irritation solubility can be miscible with water, soluble in benzene, acetone, chloroform density 1.109 boiling point 100-135 ℃(26.67) refractive index 1.4650 flash point 110 ℃ |
| Use | One of the most important characteristics of crown ether is that it can form stable complexes with various metal salts, ammonium salts, organic cationic compounds, etc. Using this property, various salts can be dissolved in organic solvents. Crown ether can be placed in the cationic chelate ring. At the same time, due to the outward organic genes, it can generate complexes, and it can also be dissolved in non-polar organic solvents. At this time, the unsolvated anion exists in the solvent as a bare anion, so the activity is extremely high. Crown ethers can dissolve alkali metals and organic alkali metal compounds in organic solvents. Therefore, it has been widely used in organic synthesis, optical resolution, heavy metal chelation, separation, analysis, and physiologically active medicine and biochemistry. For example, it is used as a phase transfer catalyst to make many reactions that are difficult to react or even do not occur under traditional conditions. |
Crownethers - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/38 - Irritating to eyes and skin. R36 - Irritating to the eyes R20/22 - Harmful by inhalation and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S36 - Wear suitable protective clothing. |
| UN IDs | 2810 |
| WGK Germany | 3 |
| RTECS | SB0200000 |
| FLUKA BRAND F CODES | 10-21 |
| TSCA | Yes |
| HS Code | 29329995 |
| Hazard Note | Irritant |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orl-rat: 1410 mg/kg DCTODJ 1,339,78 |
Crownethers - Reference Information
Open Data Unverified Data
| LogP | -0.9 at 20℃ and pH7.7 |
| surface tension | 68.5mN/m at 1g/L and 20 ℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| uses | 15-crown ether -5 is used as a phase transfer catalyst in organic synthesis chemistry; complexing agent, extractant for separation and extraction of precious metals and rare earth elements, ion conductive materials for electronic industry, materials for making liquid crystal display elements. One of the most important characteristics of crown ether is that it can form stable complexes with various metal salts, ammonium salts, organic cationic compounds, etc. Using this property, various salts can be dissolved in organic solvents. Crown ether can be placed in the cationic chelate ring. At the same time, due to the outward organic genes, it can generate complexes, and it can also be dissolved in non-polar organic solvents. At this time, the unsolvated anion exists in the solvent as a bare anion, so the activity is extremely high. Crown ethers can dissolve alkali metals and organic alkali metal compounds in organic solvents. Therefore, it has been widely used in organic synthesis, optical resolution, heavy metal chelation, separation, analysis, and physiologically active medicine and biochemistry. For example, as a phase transfer catalyst, many reactions that are difficult to react or even do not occur under traditional conditions can be carried out smoothly. Such reactions have fast rate, simple conditions, convenient operation and high yield. For example, the condensation reaction yield of benzoin in aqueous solution is extremely low. If 7% of crown ether is added to the aqueous solution, benzoin with a yield of 78% can be obtained. This reaction can also be carried out in benzene (or acetonitrile). Although potassium cyanide is insoluble in benzene, if 18-crown -6 is added, not only can the reaction occur, but the yield can be as high as 95%. Toxicity of 18-Crown -6: The oral lethal dose of rats is 300mg/kg. It is irritating to eyes and skin. |
| Production method | It is usually prepared by the William Lin synthesis method, which is the reaction of alkoxide and haloalkane. |
Last Update：2024-04-09 19:43:38
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