15-CROWN-5

PRODUCT IDENTIFICATION

CAS NO. 33100-27-5

15-CROWN-5

EINECS NO. 251-379-6
FORMULA C10H20O5
MOL WT. 220.27

H.S. CODE

2932.99

TOXICITY

Oral rat LD50: 1410 mg/kg
SYNONYMS 5-Crown 5-Ether;
1,4,7,10,13-Pentaoxa-cyclopentadecane; Crown ether 15-crown-5;

CLASSIFICATION

CROWN ETHERS /

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE Clear liquid
MELTING POINT  
BOILING POINT  
SPECIFIC GRAVITY 1.11
SOLUBILITY IN WATER miscible
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS

 

REFRACTIVE INDEX

 
FLASH POINT

110 C

STABILITY Stable under ordinary conditions. Moisture sensitive

GENERAL DESCRIPTION AND APPLICATIONS

Crown Ether is a macrocyclic polyether whose structure contains hydrogen, carbon and oxygen atoms. Each oxygen atoms are confined between two carbon atoms and exhibits a conformation with a hole (accordingly called "crown"). The common names of Crown Ethers have a prefix to designate the total number of atoms in the cycle and a suffix to designate the number of oxygen atoms in the cycle. For example, 15-crown-5 is composed of 15 atoms in the cycle, 5 of which are O and 10 of which are C.

As an ether, crown ethers are soluble in non-polar solvents. They are capable of strong solvency binding cations in their central cavity. The exterior of the ring is hydrophobic. The size of the interior central cavity, fused ring system, and side chains and functional groups determine the solvency capacity of the cation and the power of hydrophobic.

The main characteristic of crown ether is the complexation of the ether oxygens with various ionic species. If metalic elements pass through the center of the hole, they stick to oxygen atoms. The crown compound is then termed "host-guest" chemistry; Crown Ether acts as the "host" taking ionic species as its "guest". Crown compounds locks guest atoms in a solution and wrap around it. Crown ethers are used in PTC (phase-transfer catalysts) system and in encouraging the solubility of inorganic compounds in organic solvents to promote chemical reaction.  'Host-Guest' chemistry of crown ethers can be a key to identify the  move of essential elements in the body and can play the part of very complicated biological reactions such as enzyme's functions, which can be applied to develop new pharmaceuticals. Other compounds that have host cavity include cyclodextrins, calixarenes, cucurbiturils and porphyrins..

Cyclen (1,4,7,10-tetraazacyclododecane) is the aza analogues of crown ethers with repeating (-CH2CH2N) units. Cyclam is 1,4,8,11-Tetraazacyclotetradecane with repeating (-CH2CH2CH2N) units. They are starting materials to produce macrocyclic polyamine metal-complexing agents. They coordinate more than one metal ions in their central cavity. They are used as a ligand in chemistry for the applications of diagnostic imaging technique to identify medical condition or disease and for the development of medication as a therapeutic agent and pharmaceutic aid.

SALES SPECIFICATION

APPEARANCE

clear liquid

ASSAY

98.0% min
COLOR, APHA 20 max
TRANSPORTATION
PACKING

 

HAZARD CLASS  
UN NO.  
OTHER INFORMATION
Hazard Symbols: XN, Risk Phrases: 22, Safety Phrases:

GENERAL DESCRIPTION OF ETHER

Ether is any of a number of organic compounds characterized by an oxygen atom joined with single bonds by two carbon atoms that are part of hydrocarbon groups. The general formula is R-O-R', where R and R' are alkyl or aromatic groups. Ethers are formed by the condensation of two alcohols by heating with sulfuric acid; the reaction is one of dehydration. Ethers can be prepared from alkyl halide reacted with metallic alkoxide (called Williamson synthesis). Ethers are similar to alcohols but are generally less dense, less soluble in water, and have lower boiling points. They are relatively unreactive, which makes them valuable solvents. But ethers will be cleaved at high temperatures by concentrated hydrogen halides. Ethers have relatively low boiling point compare to alkanes as they don't form hydrogen bonds each other. Ethers are more lipophilic than esters [R-C(=O)-O-R']or amides [RCO-NH2]. Ethers are widely used as solvents for various organic reactions because they are relatively the least reactive among common organic compounds except alkanes and fluorocarbons. The common reaction of ethers is cleavage of the C–O bond by strong acids either in linear chain or cyclic structure. Ethers in which oxygen is bonded to primary and secondary alkyl groups can form peroxide compounds in the presence of gaseous oxygen due to two unpaired electrons in oxygen. Ethers can act as Lewis bases in chemical reactions. Commonly, ethers are named simply in listing the alkyl groups in alphabetical order or alkane order such as ethyl methyl ether or methyl ethyl ether, which is methoxyethane in IUPAC nomenclature ( the formula of "alkoxyalkane" ). When ether is a parts of complex molecule or aromatic derivatives, it is described as an alkoxy substituent such as methoxybenzene ( trivial name is anisole). The methoxy prefix indicates the function methyl group joined by single bonds to an oxygen atom, with the general formula  -O-CH3. Cyclic ethers have ring structure where the oxygen has become part of the ring. The term of epoxide indicate three membered cyclic ether (also called oxirane) in which an oxygen atom is joined to each of two carbon atoms that are already bonded to each other; four membered cyclic ether is called oxetane; five membered cyclic ether, furan (or oxolane); six membered cyclic ether, pyran (also called oxane) respectively. Their unhindered oxygen atom carries two unshared pairs of electrons - a structure which favors the formation of coordination complexes and the solvation of cations. Cyclic ethers are used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. Crown Ether is a macrocyclic polyether whose structure contains hydrogen, carbon and oxygen atoms. Each oxygen atoms are confined between two carbon atoms and exhibits a conformation with a hole (accordingly called "crown").  Anisole is one of the simplest aromatic compound to which ether group is linked. But it is different with aromatic compounds like furan where the oxygen is a part of the ring.  Anisole, C6H5OCH3 (methyl phenyl ether), is a clear liquid that is soluble in ether and alcohol; insoluble in water; boiling point 155 C. Anisole and its derivatives are used as solvents and in perfumery. Anisole can be obtained from anise seed. Anisic acid, p-methoxybenzoic acid, is a part of cresol class antiseptic compounds. It is also used as an insect repellent and ovicide. Anisole, anisic acid, and their derivatives are also widely used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals.
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