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| | 18-Crown-6 Basic information |
| | 18-Crown-6 Chemical Properties |
| Melting point | 42-45 °C(lit.) | | Boiling point | 116°C 0,2mm | | density | 1,175 g/cm3 | | refractive index | 1.4580 (estimate) | | Fp | >230 °F | | storage temp. | Store below +30°C. | | solubility | Chloroform (Slightly), Methanol (Very Slightly) | | form | Crystals or Crystalline Mass or Liquid | | color | White or clear colorless | | Water Solubility | SOLUBLE | | Sensitive | Hygroscopic | | Merck | 14,2602 | | BRN | 1619616 | | Stability: | Stable. Incompatible with strong acids, strong oxidizing agents. | | InChIKey | XEZNGIUYQVAUSS-UHFFFAOYSA-N | | CAS DataBase Reference | 17455-13-9(CAS DataBase Reference) | | NIST Chemistry Reference | 1,4,7,10,13,16-Hexaoxacyclooctadecane(17455-13-9) | | EPA Substance Registry System | 1,4,7,10,13,16-Hexaoxacyclooctadecane (17455-13-9) |
| Hazard Codes | Xn,Xi | | Risk Statements | 22-36/37/38-36-20/22-20/21/22 | | Safety Statements | 26-36-39 | | RIDADR | 2811 | | WGK Germany | 3 | | RTECS | MP4500000 | | F | 10 | | TSCA | Yes | | HazardClass | 6.1(b) | | PackingGroup | III | | HS Code | 29329995 | | Toxicity | LD50 orally in Rabbit: 525 mg/kg LD50 dermal Rabbit 3888 mg/kg |
| | 18-Crown-6 Usage And Synthesis |
| Chemical Properties | slightly yellow solid | | Uses | A useful phase transfer catalyst. | | Uses | 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). | | Uses | 18-Crown-6 may be used to catalyze the N-alkylation of heterocyclic compounds and allylation of functionalized aldehydes. | | Definition | ChEBI: 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. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 39, p. 2445, 1974 DOI: 10.1021/jo00930a037 | | 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. | | 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 | POTASSIUM CYANIDE-->Alkali Metals, plasma standard solution, Specpure, Ba,Be,Ca,Cs,K,Li,Mg,Na,Rb,Sr, 100μg/ml-->15-Crown-5-->GLOBULINS, CAT GAMMA | | Preparation Products | 1,1'-DIMETHYLFERROCENE-->N,N-Dimethylethylenediamine-->5-Bromoindazole-->3-PHENOXYPHENYLACETONITRILE-->1,3-THIAZOLIDIN-2-ONE-->Cefpodoxime proxetil-->1,2-EPOXYCYCLODODECANE-->2,4-DIAMINO-6-FLUOROPYRIMIDINE-->[(2-OXO-2H-CHROMEN-7-YL)OXY]ACETIC ACID-->3-AMINO-2-FLUORO-4-PICOLINE-->5-AMINOMETHYL-PYRROLIDIN-2-ONE-->2-AMINO-4,6-DIFLUOROPYRIMIDINE-->2-(4-BROMOPHENYL)THIOPHENE-->4-AMINO-2,6-DIFLUOROPYRIMIDINE-->N,N,N',N'-Tetraphenylbenzidine |
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