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
12 Principles of Green Chemistry: Principle 9—Catalytic reagents (as selective as possible) are superior to stoichiometric reagents.
| assay | ≥99.0% |
| form | solid |
| functional group | ether |
| greener alternative category | Aligned  |
| greener alternative product characteristics | Catalysis Learn more about the Principles of Green Chemistry . |
| InChI | 1S/C12H24O6/c1-2-14-5-6-1 |
| InChI key | XEZNGIUYQVAUSS-UHFFFAOYSA |
| mp | 42-45 °C (lit.) |
| Quality Level | 200 |
| SMILES string | O1CCOCCOCCOCCOCCOCC1 |
| sustainability | Greener Alternative Product |
| 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. |
| General description: | We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here  for more information. |
| 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 |