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18-Crown-6

CAS No.
17455-13-9
Chemical Name:
18-Crown-6
Synonyms
1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE;8-Crown-6;HEXAOXACYCLOOCTADECANE;18-CROWN 6-ETHER;Ethylene oxide cyclic hexamer;18-Crown ether-6;18-CROWN-6;NSC 159836;18-Crown-6 99%;18-Crown-6,99%
CBNumber:
CB4445218
Molecular Formula:
C12H24O6
Molecular Weight:
264.32
MDL Number:
MFCD00005113
MOL File:
17455-13-9.mol
MSDS File:
SDS
Last updated:2024-11-01 18:09:03

18-Crown-6 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
Indirect Additives used in Food Contact Substances 1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE
CAS DataBase Reference 17455-13-9(CAS DataBase Reference)
FDA UNII 63J177NC5B
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

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
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
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
NFPA 704
1
2 0

18-Crown-6 price More Price(61)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.11684 Crown ether/18-Crown-6 for synthesis 17455-13-9 2g $26.1 2024-03-01 Buy
Sigma-Aldrich 8.11684 Crown ether/18-Crown-6 for synthesis 17455-13-9 5G $33.3 2024-03-01 Buy
Sigma-Aldrich 8.11684 Crown ether/18-Crown-6 for synthesis 17455-13-9 25g $153 2024-03-01 Buy
Sigma-Aldrich 28125 18-Crown-6 purum, ≥99.0% (GC) 17455-13-9 5g $46.5 2024-03-01 Buy
Sigma-Aldrich 186651 18-Crown-6 99% 17455-13-9 5G $113 2024-03-01 Buy
Product number Packaging Price Buy
8.11684 2g $26.1 Buy
8.11684 5G $33.3 Buy
8.11684 25g $153 Buy
28125 5g $46.5 Buy
186651 5G $113 Buy

18-Crown-6 Chemical Properties,Uses,Production

Chemical Properties

slightly yellow solid

Uses

18-Crown-6 may be used to catalyze the N-alkylation of heterocyclic compounds and allylation of functionalized aldehydes.

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).

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.]

112-27-6
17455-13-9
Synthesis of 18-Crown-6 from Triethylene glycol
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Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
18-Crown-6 pictures 2024-11-27 18-Crown-6
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US $0.00 / KG 1KG 99%min 30tons/month WUHAN FORTUNA CHEMICAL CO., LTD
18-Crown-6 pictures 2024-11-19 18-Crown-6
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US $1.00 / g 1g 99% 10000 Apeloa production Co.,Limited
18-crown - 6 ether  pictures 2024-11-01 18-crown - 6 ether
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US $0.00 / PCS 1PCS 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
  • 18-Crown-6 pictures
  • 18-Crown-6
    17455-13-9
  • US $0.00 / KG
  • 99%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • 18-Crown-6 pictures
  • 18-Crown-6
    17455-13-9
  • US $1.00 / g
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  • Apeloa production Co.,Limited
18-CROWN-6 CROWN-18-5-ETHER CROWN ETHER/18-CROWN-6 AKOS BBS-00004361 CROWN ETHER/18-CROWN-6 FOR SYNTHESIS 18 and crown ether 18-Crown-6 >=99.0% 18-Crown-6 99% 18-Crown-6 puruM, >=99.0% (GC) 18 - the chaMpions league - 6 - ether 1,4,7,10,13,16-Hexaoxacyclooctadecane 99% 1,4,7,1,13,16-Hexaoxacyclooctadecane 18-CROWN-6, 99.5+% 18-CROWN-6(1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE) 18-Crown-6, 98+% 1,4,7,10,13,16-HEXOXA-CYCLO-OCTADECANE 18-Crown-6,99% 1,4,7,10,13,16-Hexanoxacyclooctadecane. 18-Crown-6-ether 99% 1,4,7,10,13,16-Hexaoxacyclooctadecane (18-Crown-6) 18-CROWN-6 99.8% Crown/18-crown-6 1,4,7,10,13,16-Hexaoxacyclooctadecane, Hexaoxacyclooctadecane 18-CROWN-6-ETHER pure NSC 159836 18-Crown-6/1,4,7,10,13,16-HexaoxacyclooCLadecane 18-Crown-6, 99% 25GR 18-Crown-6, 99% 5GR JACS-17455-13-9 18-Crown-6 solution 18-Crown-6, 99%, reagent grade 18-Crown 6-Ether > 18-Crown-6(1,4,7,10,13,17-Hexaoxacyclooctadecane),>99% 18-Crown-6(1,4,7,10,13,18-Hexaoxacyclooctadecane),>99% High quality 18-Crown-6 CAS 17455-13-9 Crown Ether 18-Crown 6-Ether, ≥ 98.0% 1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE 18-CROWN 6-ETHER HEXAOXACYCLOOCTADECANE 8-Crown-6 18-Crown ether-6 Ethylene oxide cyclic hexamer N,N-Diethylformamide 617-84-5 18-Crown-8-Ether Octadecyl hexaether 18-Crown-6 1,4,7,10,13,16-Hexaoxacyclooctadecane (1,4,7,10,13,16-hexaoxacyclooctadecane) Crownwhitextl 18-Crown-6-ether 18-Crown-6-ether 98% For Synthesis 17455-13-9 7455-13-9 C12H24O6 Synthetic Reagents Trace Analysis Reagents General Use Macrocycles for Host-Guest Chemistry Crown Ethers Analytical Reagents Analytical Chromatography Product Catalog Chelation/Complexation Compounds