74461-33-9

Basic information

• Product Name: 1,4,10-Trioxa-7,13-diazacyclopentadecane, 7,13-bis[(4-methylphenyl)sulfonyl]-
• Synonyms: N,N'-ditosyl-1,4,10-trioxa-7,13-diazacyclopentadecane
• CAS NO: 74461-33-9
• Molecular Formula: C24H34N2O7S2
• Molecular Weight: 526.675
• Mol File: 74461-33-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 127-128 °C(Solv: ethanol (64-17-5))
• Boiling Point: 690.2±65.0 °C(Predicted)
• Density: 1.229±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,4,10-Trioxa-7,13-diazacyclopentadecane, 7,13-bis[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,10-Trioxa-7,13-diazacyclopentadecane, 7,13-bis[(4-methylphenyl)sulfonyl]-(74461-33-9)
• EPA Substance Registry System: 1,4,10-Trioxa-7,13-diazacyclopentadecane, 7,13-bis[(4-methylphenyl)sulfonyl]-(74461-33-9)

Safety Data

• Hazardous Substances Data: 74461-33-9(Hazardous Substances Data)

Usage

Molecular structure

Cyclic compound containing three oxygen atoms and two nitrogen atoms

Sulfonyl groups

Two sulfonyl groups attached to the 7th and 13th carbon atoms

Substituents

4-methylphenyl groups on the sulfonyl groups

Applications

Organic synthesis and pharmaceutical research as a building block for complex molecules

Potential uses

Development of pharmaceutical drugs and organic materials

Chemical reactivity

Sulfonyl groups can participate in a variety of chemical reactions

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 70-55-3 toluene-4-sulfonamide 
• 31255-10-4 1,2-bis-(2-bromo-ethoxy)-ethane 
• 59945-34-5 N,N'-Bis(p-tolylsulfonyl)-1,5-diamino-3-oxapentane 
• 19249-03-7 triethylene glycol di-(p-toluenesulfonate) 
• 59945-35-6 N,N'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide) 
• 7460-82-4 diethylene glycol ditosylate 
• 5414-19-7 1,1'-oxybis(2-bromo-ethane) 

Downstream Products

• 121031-82-1 4,7,10-tris(p-tolylsulphonyl)-16,19,24-trioxa-1,4,7,10,13-penta-azabicyclo<11.8.5>hexacosane 
• 121031-85-4 4,9-bis(p-tolylsulphonyl)benz-15,18,23-trioxa-1,4,9,12-tetra-azabicyclo<10.8.5>pentacosane 
• 121031-87-6 4,11-bis(p-tolylsulphonyl)-6,9-etheno-17,20,25-trioxa-1,4,11,14-tetra-azabicyclo<12.8.5>heptacosa-6,8-diene 
• 113917-91-2 4,13-bis(p-tolylsulphonyl)-7,10,19,22,27-pentaoxa-1,4,13,16-tetra-azabicyclo<14.8.5>-nonacosane 
• 118075-01-7 4,10-bis(p-tolylsulphonyl)-7,16,19,24-tetraoxa-1,4,10,13-tetra-azabicyclo<11.8.5>hexacosane 
• 113917-86-5 7,13-bis<2-(tolylsulphonylamino)ethyl>-1,4,10-trioxa-7,13-diazacyclopentadecane 
• 31249-95-3 Kryptofix 21 

Relevant articles and documents

MACROHETEROCYCES. XXXVI. A CONVENIENT METHOD FOR SYNTHESIS OF DI- AND POLYAZACROWN ETHERS

A method is proposed for the production of di- and polyazacrown ethers by the condensation of bissulfonamides with dibromides or ditosyloxy derivatives in a two-phase aqueous alkali-toluene (benzene) system.The optimum concentration range for the substrate and the alkylating agent is 0.017-0.1 M.The catalytic activity of the quaternary ammonium salts decreases in the order (Bu)4NI > (Bu4)NBr > (Bu4)NCl > (Bu4)NHSO4 > (C2H5)3C6H5CH2NCl >> (Et)4NI > (Et)4NBr.The highest yields of te 12-membered azacrown ethers are obtained in the presence of lithium hyroxide, and the largest yields of the crown ethers with larger ring sizes are obtained in the presence of sodium or potassium hydroxide, and this is probably due to the matrix effects of the cation.

MACROHETEROCYCLES. PART 44. FACILE SYNTHESIS OF AZACROWN ETHERS AND CRYPTANDS IN A TWO-PHASE SYSTEM

A facile procedure is proposed for the preparation of azacrown ethers and cryptands by condensation of dibromides or ethylene glycol bis(toluene-p-sulphonate)s with acyclic bis(sulphonamide)s or with bisdiazacrown ethers, respectively.The reaction was carried out in a two-phase system of aqueous alkali-toluene (benzene)in the presence of quaternary ammonium salts as phase transfer catalysts.The catalytic activity decreased in the sequence: Bu4NI ca.Bu4NBr > Bu4NCl > Bu4NHSO4 > Et3NCH2C6H5NCl.Maximum yields of twelve-membered azacrown ethers are obtained when lithium hydroxide is used, while crown ethers of larger size are observed in the presence of sodium or potassium hydroxides; this may be due to a template effect.