18-Crown-6
- Iupac Name：1,4,7,10,13,16-hexaoxacyclooctadecane
- CAS No.: 17455-13-9
- Molecular Weight：264.31536
- Modify Date.: 2022-11-22 21:15
- Introduction:
slightly yellow solid
18-crown-6 is a crown ether that is cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13 and 16 have been replaced by oxygen atoms. It has a role as a phase-transfer catalyst. It is a crown ether and a saturated organic heteromonocyclic parent.
View more+
1. Names and Identifiers
- 1.1 Name
- 18-Crown-6
- 1.2 Synonyms
[18]crown-6 1,4,7,10,13,16-Hexanoxacyclooctadecane 1,4,7,10,13,16-Hexaoxacyclooctadecane 18C6 18-CROWN 6-ETHER 18-Crown ether-6 18-crown-6 ether 5-19-12-00601 AKOS BBS-00004361 Coronand 18C6 Crown Ether O 18 CROWN ETHER/18-CROWN-6 CROWN-18-5-ETHER EINECS 241-473-5 ethylene oxide cyclic hexamer HEXAOXACYCLOOCTADECANE JACS-17455-13-9 MFCD00005113 NSC 159836 UNII-63J177NC5B
- View all
- 1.3 CAS No.
- 17455-13-9
- 1.4 CID
- 28557
- 1.5 EINECS(EC#)
- 241-473-5
- 1.6 Molecular Formula
- C12H24O6 (isomer)
- 1.7 Inchi
- InChI=1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2
- 1.8 InChIkey
- XEZNGIUYQVAUSS-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1COCCOCCOCCOCCOCCO1
- 1.10 Isomers Smiles
- C1COCCOCCOCCOCCOCCO1
2. Properties
- 2.1 Density
- 0.995
- 2.1 Melting point
- 36-40℃
- 2.1 Boiling point
- 395.8 oC at 760 mmHg
- 2.1 Refractive index
- 1.4577 (50 C)
- 2.1 Flash Point
- >110℃
- 2.1 Precise Quality
- 264.15700
- 2.1 PSA
- 55.38000
- 2.1 logP
- 0.09960
- 2.1 Appearance
- White or clear colorless Crystals or Crystalline Mass or Liquid
- 2.2 Storage
- Hygroscopic. Ambient temperatures.
- 2.3 Chemical Properties
- slightly yellow solid
- 2.4 Color/Form
- White or clear colorless
- 2.5 Water Solubility
- SOLUBLE
- 2.6 Stability
- Stable. Incompatible with strong acids, strong oxidizing agents.
- 2.7 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- It is usually prepared by Williamlin synthesis, that is, it reacts with alkoxide and haloalkane.?Uses: One of the most important features of crown ethers 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 ethers can chelate cations inside, and at the same time, they can form complexes due to outward-facing organic genes, and can also be dissolved in non-polar organic solvents.?At this time, the unsolvated anions exist in the solvent in the form of bare anions, so the activity is extremely large.?Crown ethers can dissolve alkali metal and organic alkali metal compounds in organic solvents.?Therefore, it has found wide applications in organic synthesis, optical resolution, heavy metal chelation, separation, analysis, and physiologically active medicine and biochemistry.?For example, it can be used as a phase transfer catalyst to enable many reactions that are difficult to react under conventional conditions, or even not occur, to proceed smoothly. Such reactions have a fast rate, simple conditions, convenient operation and high yield.?For example, the yield of the condensation reaction of benzoin in an aqueous solution is extremely low. If 7% of crown ether is added to the aqueous solution, the benzoin can be obtained in a yield of 78%.?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 take place, but the yield can be as high as 95%.?Toxicity of 18-crown-6: Oral lethal dose in rats is 300 mg/kg.?Irritating to eyes and skin.
- View all
- 3.2 Purification Methods
- Recrystallise it from acetonitrile and dry it in a vacuum. Purify it also by precipitating the 18-crown-6/nitromethane 1:2 complex with Et2O/nitromethane (10:1 mixture). The complex is decomposed in vacuum whereby 18-crown-6 distils off under the reduced pressure. [Beilstein 19/12 V 601.] 18-Crown-6 Preparation Products And Raw materials Raw materials
- 3.3 Usage
- A useful phase transfer catalyst.
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R20/22;R36
- 4.1 Safety Statements
- S26;S39
- 4.1 Packing Group
- III
- 4.1 Hazard Class
- 6.1(b)
- 4.1 Hazard Declaration
- H302
- 4.1 RIDADR
- 2811
- 4.1 Caution Statement
- P301 + P312 + P330
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- MP4500000
- 4.1 Report
-
Reported in EPA TSCA Inventory.
- 4.2 Safety
-
Hazard Codes: 
Xn,
Xi
Risk Statements: 22-36/37/38-36-20/22-20/21/22
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R36:Irritating to eyes.
R20/22:Harmful by inhalation and if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36-39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S39:Wear eye / face protection.
RIDADR: 2811
WGK Germany: 3
RTECS: MP4500000
F: 10
HazardClass: 6.1(b)
PackingGroup of 18-Crown-6 (CAS NO.17455-13-9): III
- View all
- 4.3 Sensitive
- Hygroscopic
- 4.4 Specification
-
18-Crown-6 (CAS NO.17455-13-9), its Synonyms are 1,4,7,10,13,16-Hexanoxacyclooctadecane ; 1,4,7,10,13,16-Hexaoxacyclooctadecane ; Ethylene oxide cyclic hexamer . It is slightly yellow solid.
- 4.5 Toxicity
- LD50 orally in Rabbit: 525 mg/kg LD50 dermal Rabbit 3888 mg/kg
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
17455-13-9Total: 36 Synthesis Route
9. Other Information
- 9.0 Usage
- 18-Crown-6 is used as an efficient phase transfer catalyst and as a complexing agent with a variety of small cation. It is involved in the synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6. It facilitates the solubility of potassium permanganate in benzene, which is used for oxidizing the organic compounds. It is used to accelerate various substitution reactions as well as enhances the power of nucleophiles such as potassium acetate. It is utilized in the alkylation reactions in the presence of potassium carbonate, N-alkylation of glutarimide and succinimide with dimethylcarbonate. The complex formed by its reaction with potassium cyanide acts as a catalyst in the cyanosilylation of aldehydes, ketones and quinines with trimethylsilyl cyanide (TMSCN).
- 9.1 Merck
- 14,2602
- 9.2 BRN
- 1619616
- 9.3 Chemical Properties
- slightly yellow solid
- 9.4 Uses
- A useful phase transfer catalyst.
- 9.5 Purification Methods
- Recrystallise it from acetonitrile and dry it in a vacuum. Purify it also by precipitating the 18-crown-6/nitromethane 1:2 complex with Et2O/nitromethane (10:1 mixture). The complex is decomposed in vacuum whereby 18-crown-6 distils off under the reduced pressure. [Beilstein 19/12 V 601.]
- 9.6 Uses
- 18-Crown-6 may be used to catalyze the N-alkylation of heterocyclic compounds and allylation of functionalized aldehydes.
- 9.7 Synthesis Reference(s)
- The Journal of Organic Chemistry, 39, p. 2445, 1974 DOI: 10.1021/jo00930a037
- 9.8 General Description
- 18-Crown-6 is the simplest crown ether that can be prepared by reacting triethylene glycol with triethylene glycol dichloride in the presence of potassium hydroxide as a base. 18-Crown-6 can solubilize metal salts, particularly potassium salts, in nonpolar and dipolar aprotic solvents. Thus, it is widely used as a phase transfer catalyst. It can also be used as a metal complexing agent to prepare a variety of molecular complexes.
- 9.9 Storage Conditions
- It is usually prepared by Williamlin synthesis, that is, it reacts with alkoxide and haloalkane.?Uses: One of the most important features of crown ethers 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 ethers can chelate cations inside, and at the same time, they can form complexes due to outward-facing organic genes, and can also be dissolved in non-polar organic solvents.?At this time, the unsolvated anions exist in the solvent in the form of bare anions, so the activity is extremely large.?Crown ethers can dissolve alkali metal and organic alkali metal compounds in organic solvents.?Therefore, it has found wide applications in organic synthesis, optical resolution, heavy metal chelation, separation, analysis, and physiologically active medicine and biochemistry.?For example, it can be used as a phase transfer catalyst to enable many reactions that are difficult to react under conventional conditions, or even not occur, to proceed smoothly. Such reactions have a fast rate, simple conditions, convenient operation and high yield.?For example, the yield of the condensation reaction of benzoin in an aqueous solution is extremely low. If 7% of crown ether is added to the aqueous solution, the benzoin can be obtained in a yield of 78%.?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 take place, but the yield can be as high as 95%.?Toxicity of 18-crown-6: Oral lethal dose in rats is 300 mg/kg.?Irritating to eyes and skin.
- View all
- 9.10 Manufacturing Info
- 1,4,7,10,13,16-Hexaoxacyclooctadecane: ACTIVE
10. Computational chemical data
- Molecular Weight: 264.31536g/mol
- Molecular Formula: C12H24O6
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 264.15728848
- Monoisotopic Mass: 264.15728848
- Complexity: 108
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 6
- Topological Polar Surface Area: 55.4
- Heavy Atom Count: 18
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADceBwOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAAAACggAIAAAAABAAAAAAAAAAAAAAAAAAAAAAAAAABAAAAAAACAAAAAAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
What Makes 18-Crown-6 Coordination Compounds Shine? A Look into Their Photoluminescence and Nonlinear Optical Properties 18-Crown-6 coordination compounds exhibit fascinating properties in terms of ph..
-
The most notable characteristic of 18-Crown-6 is its ability to complex with cations, especially alkali metal ions, and form different metal ion complexes depending on the size of the ring. Applicatio..
-
I know crown ethers can be used to complex metal ions. Question: What important properties do 18-crown-6 change during the benzannulation from 18-crown-6 to DB18C6 (dibenzo-18-crown-6)? How do these ..
-
18-crown-6 (18C6, 18c6, [18]-Crown-6) functions as a ligand for some metal cations with a particular affinity for potassium cations (binding constant in methanol: 106 M−1) [1]. It can solubilize..
12. Recommended Suppliers
-
- Products:Chemical products
- Tel:86-571-88938639
- Email:sales-gc@dycnchem.com
18-Crown-6
- Purity:99%Packing: 200kg/bag FOB
- Price: 1 USD/kilogram
- Time: 2023/09/20
Inquire
-
- Products:API,fine chemical&its intermediates,biological chemistry
- Tel:0086-27-59207850
- Email:info@fortunachem.com
-
- Products:Pharmaceutical Intermediate , Apis , Food Additives , Herbal Extracts , Fine Chemicals , ...
- Tel:00-86-13023277276
- Email:hanna@xljxcl.com
-
- Products:Division I, the main production Lead acetate phenylacetamide Cyromazine quality is very good!
- Tel:86-185-31123677
- Email:xing@yan-xi.com
-
- Products:Pharmaceutical, chemical technology research and development
- Tel:086-0532-80960264
- Email:derek@believechem.com
13. Realated Product Infomation
skype
12YRS
