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)

Flash point:

>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)

Safety Information

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

MSDS

• Language:English Provider:Hexaoxacyclo-octadecane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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18-crown-6 is a crown ether that is cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13 and 16 have been replaced by oxygen atoms.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 (17455-13-9)Related Product Information

• Dimethyl ether
• 2-Butoxyethanol
• Ethylbenzene
• 12-Crown-4
• Octadecane
• 4'' 4 (5 )-DI-TERT.BUTYLDICYCLOHEXANO-18-CROWN-6,MIXTUREOFISOMERS
• (+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXYLIC ACID
• Diethyl ether
• Dicyclohexano-18-crown-6
• 1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE-2-METHANOL
• 4-ACRYLAMIDOBENZO-18-CROWN-6 98%
• Isobutyl iodide
• 4',4''(5'')-di-tert-butyldibenzo-18-crown-6, mixed isomers,4,4'-Di-tert-butyldibenzo-18-crown-6
• 4-AMINOBENZO-18-CROWN-6 PURUM,97%
• 4-Nitrobenzo-18-crown-6,99%
• 4-VINYLBENZO-18-CROWN-6 97%
• 4-(Chloromethyl)styrene homopolymer
• Dibenzo-18-crown-6,min.98%,1,4,7,14,17,20-HEXAOXA[7.7]ORTHOCYCLOPHANE<BR> DIBENZO-18-CROWN-6,Dibenzo-18-crown-6, 98+%