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18-Crown-6

18-Crown-6 structure

CAS No:
17455-13-9
Formula:
C12H24O6
Chemical Name:
18-Crown-6
Synonyms:
1,4,7,10,13,16-Hexaoxacyclooctadecane;18-Crown-6 ether;Ethylene oxide cyclic hexamer;18-Crown-6;18C6;18-Crown ether-6;NSC 159836;Coronand 18C6;Crown Ether O 18;134316-24-8;63172-42-9;65154-22-5;66037-87-4;71210-94-1;71211-03-5;71245-01-7;71251-38-2;71251-42-8;71251-39-3;168081-58-1
Categories:
Chemical Reagents > Organic Reagents

Description

slightly yellow solid

18-crown-6 is a crown ether that is cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13 and 16 have been replaced by oxygen atoms.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

18-Crown-6 Basic Attributes

Molecular Weight：

264.32

Exact Mass：

264.32

BRN：

1619616

EC Number：

241-473-5

UNII：

63J177NC5B

NSC Number：

159836

DSSTox ID：

DTXSID7058626

HScode：

29329995

Characteristics

PSA：

55.4

XLogP3：

-0.7

Appearance：

White or clear colorless Crystals or Crystalline Mass or Liquid

Density：

1.237 g/cm³

Melting Point：

39 °C

Boiling Point：

264 °C @ Press: 33 Torr

Flash Point：

>230 °F

Refractive Index：

1.4580 (estimate)

Water Solubility：

SOLUBLE

Storage Conditions：

Store at 0-5°C

Vapor Pressure：

4.09E-06mmHg at 25°C

Toxicity：

LD50 orally in Rabbit: 525 mg/kg LD50 dermal Rabbit 3888 mg/kg

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

2811

wgk germany：

hazard class code：

22-36/37/38-36-20/22-20/21/22

safety instructions：

26-36-39

RTECS Number：

MP4500000

Marks：

Xn,Xi

Stability/Shelf Life：

Stable. Incompatible with strong acids, strong oxidizing agents.

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (98.05%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 205 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

18-crown-6

18-Crown-6 Use and Manufacturing

Methods of Manufacturing

It is usually prepared by Williamlin synthesis, that is, it reacts with alkoxide and haloalkane. Uses: One of the most important features of crown ethers is that it can form stable complexes with various metal salts, ammonium salts, organic cationic compounds, etc. Using this property, various salts can be dissolved in organic solvents. Crown ethers can chelate cations inside, and at the same time, they can form complexes due to outward-facing organic genes, and can also be dissolved in non-polar organic solvents. At this time, the unsolvated anions exist in the solvent in the form of bare anions, so the activity is extremely large. Crown ethers can dissolve alkali metal and organic alkali metal compounds in organic solvents. Therefore, it has found wide applications in organic synthesis, optical resolution, heavy metal chelation, separation, analysis, and physiologically active medicine and biochemistry. For example, it can be used as a phase transfer catalyst to enable many reactions that are difficult to react under conventional conditions, or even not occur, to proceed smoothly. Such reactions have a fast rate, simple conditions, convenient operation and high yield. For example, the yield of the condensation reaction of benzoin in an aqueous solution is extremely low. If 7% of crown ether is added to the aqueous solution, the benzoin can be obtained in a yield of 78%. This reaction can also be carried out in benzene (or acetonitrile). Although potassium cyanide is insoluble in benzene, if 18-crown-6 is added, not only can the reaction take place, but the yield can be as high as 95%. Toxicity of 18-crown-6: Oral lethal dose in rats is 300 mg/kg. Irritating to eyes and skin.

Uses

A useful phase transfer catalyst.

Manufacturing Info：

1,4,7,10,13,16-Hexaoxacyclooctadecane: ACTIVE

Computed Properties

Molecular Weight:264.31
XLogP3:-0.7
Hydrogen Bond Acceptor Count:6
Exact Mass:264.15728848
Monoisotopic Mass:264.15728848
Topological Polar Surface Area:55.4
Heavy Atom Count:18
Complexity:108
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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