18-Crown-6
ALDRICH/274984 - ≥99.0%
Synonym: 1,4,7,10,13,16-
CAS Number: 17455-13-9
Empirical Formula (Hill Notation): C12H24O6
Molecular Weight: 264.32
EC Number: 241-473-5
MDL Number: MFCD00005113
Linear Formula: C12H24O6
Product Type: Chemical
| assay | ≥99.0% |
| form | solid |
| InChI | 1S/C12H24O6/c1-2-14-5-6-1 |
| InChI key | XEZNGIUYQVAUSS-UHFFFAOYSA |
| mp | 42-45 °C (lit.) |
| Quality Level | 200  |
| SMILES string | O1CCOCCOCCOCCOCCOCC1 |
| Application: | 18-Crown-6 can be used as a catalyst for: • N-alkylation of heterocyclic compounds in the presence of tert-butoxide base. • Allylation of aldehydes to corresponding homoallylic alcohols using potassium allyltrifluoroborate. • Preparation of N-propargylpyrrole by the reaction of pyrrole with potassium hydroxide. • Polymerization of methacrylic esters and hindered alkyl acrylates. • Chemoselective reduction of fused tetrazoles with NaBH4 and potassium hydroxide. |
| Application: | 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. |
| Application: | Can be useful as phase-transfer catalysts. |
| General description: | 18-Crown-6 is a macrocyclic polyether used to synthesize ionic liquid based crown-ether coordination compounds. 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. |
| Other Notes: | Macrocyclic polyethers with repeating (-CH2CH2O) units. The compounds are ionophoric (form stable complexes with cations). |
| Packaging: | 1 g in glass bottle |
| Symbol |  GHS07 |
| Signal word | Warning |
| Hazard statements | H302 |
| Precautionary statements | P301 + P312 + P330 |
| Hazard Codes | Xn |
| Risk Statements | 22-36/37/38 |
| Safety Statements | 26-36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥99.0% |
| mp | 42-45 °C (lit.) |
| UNSPSC | 12352005 |