33941-15-0

Basic information

• Product Name: 1,4,7,10,13-PENTAOXA-16-AZACYCLOOCTADECANE
• Synonyms: 1,4,7,10,13-PENTAOXA-16-AZACYCLOOCTADECANE;1-AZA-18-CROWN-6;1-AZA-18-CROWN 6-ETHER;AZA-18-CROWN-6;1-Aza-4,7,10,13,16-pentaoxacyclooctadecane;4,7,10,13,16-Pentaoxa-1-azacyclooctadecane;Aza-18-crown-6,98%;1-Aza-18-crown-6 >=98.0% (NT)
• CAS NO: 33941-15-0
• Molecular Formula: C₁₂H₂₅NO₅
• Molecular Weight: 263.33
• EINECS: 251-751-8
• Product Categories: Azacrown Ethers;Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry;organic building block
• Mol File: 33941-15-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 46-49 °C(lit.)
• Boiling Point: 406.57°C (rough estimate)
• Flash Point: >230 °F
• Appearance: white crystals
• Density: 1.1122 (rough estimate)
• Vapor Pressure: 9.78E-07mmHg at 25°C
• Refractive Index: 1.4287 (estimate)
• Storage Temp.: 0-6°C
• PKA: 8.69±0.20(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 1074079
• CAS DataBase Reference: 1,4,7,10,13-PENTAOXA-16-AZACYCLOOCTADECANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,7,10,13-PENTAOXA-16-AZACYCLOOCTADECANE(33941-15-0)
• EPA Substance Registry System: 1,4,7,10,13-PENTAOXA-16-AZACYCLOOCTADECANE(33941-15-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 33941-15-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystals or crystalline mass

Uses

1-Aza-18-crown-6 is used as building block for the synthesis of bis-crown ethers, lariat ethers and other monofunctionalized macrocycles. It is also used as pharmaceutical intermediate.

InChI:InChI=1/C12H25NO5/c1-3-14-5-7-16-9-11-18-12-10-17-8-6-15-4-2-13-1/h13H,1-12H2/p+1

Upstream product

• 63281-63-0 16-(p-Tolylsulfonyl)-1,4,7,10,13-pentaoxa-16-azacyclooctadecan 
• 75001-08-0 2-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl}isoindole-1,3-dione 
• 37860-51-8 tetraethylene glycol di(p-toluenesulfonate) 
• 118798-05-3 1,17-diiodo-3,6,9,12,15-pentaoxaheptadecane 
• 112-60-7 Tetraethylene glycol 
• 111-42-2 2,2'-iminobis[ethanol] 
• 638-56-2 1,11-dichloro-3,6,9-trioxaundecane 
• 85971-97-7 3,6,9,12-tetraoxa-15-azaheptadecane-1,17-diol 
• 85971-98-8 3,6,9,15-tetraoxa-12-azaheptadecane-1,17-diol 
• 25743-12-8 3,6,12,15-tetraoxa-9-azaheptadecane-1,17-diol 
• 63281-62-9 1-benzyl-1-aza-18-crown-6 
• 5197-67-1 14-chloro-3,6,9,12-tetraoxatetradecanol 
• 5197-62-6 2-[2-(chloroethoxy)ethoxy]ethanol 
• 6338-55-2 2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol 

Downstream Products

• 63281-62-9 1-benzyl-1-aza-18-crown-6 
• 107995-94-8 N-(2-nitrobenzyl)aza-18-crown-6 
• 107835-17-6 1,4,7,10,13-pentaoxa-16-(sulfanil)azacyclooctadecane 
• 74776-96-8 1,3-bis[(4,7,10,13,16-pentaoxa-1-azacyclooctadecyl)methyl]benzene 
• 156731-05-4 N-methoxymethyl-1,7,10,13,16-pentaoxa-4-azacyclooctadecane 
• 210093-67-7 C₅₃H₆₈F₆N₂O₁₀S₂ 
• 256517-53-0 1-(α-thioacetyl-m-xylyl)-4,7,10,13,16-pentaoxa-1-azacyclooctadecane 
• 256387-74-3 4,4'-diiodo-3,3'-di(18-azacrown-6-N-carbonylmethoxy)biphenyl 
• 256387-79-8 6⁴,1⁴-diiodo-6³,5²,4³,3²,2³,1³-hexa(18-azacrown-6-N-carbonylmethoxy)-p-sexiphenyl 
• 256387-82-3 8⁴,1⁴-dimethylsulfanyl-7³,6²,5³,4²,3³,2²-hexa(18-azacrown-6-N-carbonylmethoxy)-p-octiphenyl 
• 497258-51-2 N-(4-ethynylbenzoyl)monoaza-18-crown-6 
• 579510-35-3 16-[(3,3-diphenyl-3H-benzo[f]chromen-5-yl)methyl]-1,4,7,10,13-pentaoxa-16-azacyclooctadecane 

Relevant articles and documents

Aza-crown ether locked on polyethyleneimine: Solving the contradiction between transfection efficiency and safety during: In vivo gene delivery

We proposed a method using an aza-crown ether derivative to lock a hyperbranched polyethyleneimine, which endows the PEI25k with tumor targeting ability, anti-serum ability and extended circulation in the blood meanwhile retaining the high gene complexation and high transfection efficiency. The method we proposed here simultaneously endows cationic materials with high transfection efficiency and high safety, which greatly pushed the cationic materials to be applied in in vivo gene delivery.

Synthesis of monoazacrown ethers under phase-transfer catalysis

A procedure has been proposed for the synthesis of monoazacrown ethers by reaction of N-benzyldiethanolamine with oligo(ethylene glycol) bis-p-toluenesulfonates in a two-phase system aromatic hydrocarbon-50% aqueous alkali, followed by removal of the benzyl group by catalytic hydrogenolysis. The maximal yields of N-benzylaza-12-crown-4, -18-crown-6, and -21-crown-7 were achieved by adding 4-10 equiv of LiCl, BaBr2, and CsCl, respectively, to the reaction mixture, which probably indicated template effect. Pleiades Publishing, Ltd., 2012.