23978-10-1

Basic information

• Product Name: KRYPTOFIX 23
• Synonyms: KRYPTOFIX 23;KRYPTOFIX(R) 23;1,7,10,13,19-PENTAOXA-4,16-DIAZACYCLOHENEICOSANE;1,4,7,13,16-Pentaoxa-10,19-diazacycloheneicosane;1,4,7,13,16-pentaoxa-10,19-diazacyclo-heneicosane;1,4,7,13,16-pentaoxa-10,19-diazacyclohenicosane;1 4 7 13 16-PENTAOXA-10 19-DIAZACYCLO- &;KRYPTOFIX 23 97+%
• CAS NO: 23978-10-1
• Molecular Formula: C₁₄H₃₀N₂O₅
• Molecular Weight: 306.4
• EINECS: 245-964-5
• Mol File: 23978-10-1.mol

Chemical Properties

• Melting Point: 39-41 °C
• Boiling Point: 463.6°Cat760mmHg
• Flash Point: 194.4°C
• Appearance: /
• Density: 0.958g/cm³
• Vapor Pressure: 8.93E-09mmHg at 25°C
• Refractive Index: 1.41
• PKA: 8.99±0.20(Predicted)
• CAS DataBase Reference: KRYPTOFIX 23(CAS DataBase Reference)
• NIST Chemistry Reference: KRYPTOFIX 23(23978-10-1)
• EPA Substance Registry System: KRYPTOFIX 23(23978-10-1)

Safety Data

• Hazardous Substances Data: 23978-10-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H30N2O5/c1-5-17-9-10-18-6-2-16-4-8-20-12-14-21-13-11-19-7-3-15-1/h15-16H,1-14H2

Upstream product

• 50977-92-9 1,14-dihydroxy-3,12-diaza-6,9-dioxatetradecane 
• 7460-82-4 diethylene glycol ditosylate 
• 929-59-9 3,6-dioxa-1,8-diaminooctane 
• 36839-56-2 1,11-diiodo-3,6-9-trioxaundecane 
• 929-75-9 2-[2-[2-[2-aminoethoxy]ethoxy]ethoxy]ethylamine 
• 36839-55-1 1,2-bis-(2-iodoethoxy)ethane 
• 31255-10-4 1,2-bis-(2-bromo-ethoxy)-ethane 
• 31255-09-1 3,6-dioxa-1,8-octanoyl dichloride 
• 120808-60-8 10,19-bis-(p-tolylsulphonyl)-1,4,7,13,16-pentaoxa-10,19-diazacyclohemicosane 
• 31255-20-6 1,4,7,13,16-pentaoxa-10,19-diaza-cycloheneicosane-11,18-dione 
• 59945-36-7 1,11-bis(p-tolylsulphonylamino)-3,6,9-trioxaundecane 
• 59945-35-6 N,N'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide) 
• 31255-26-2 1-bromo-2-{2-[2-(2-bromoethoxy)ethoxy]-ethoxy}ethane 

Downstream Products

• 130985-65-8 N,N'-bis(2-pyridylmethyl)diaza-21-crown-7 
• 94195-17-2 10,19-dibenzyl-10,19-diaza-1,4,7,13,16-pentaoxacyclohenicosane 
• 160563-01-9 10,19-bis[(octadecylcarbamoyl)methoxyacetyl]-1,4,7,13,16-pentaoxa-10,19-diazacycloheneicosane 
• 31255-22-8 2.2.2‐crypt 

Relevant articles and documents

Steric and stereoelectronic effects in aza crown ether complexes

Stability constants and enthalpy changes determined by calorimetric titrations and supported by selected NMR titrations are reported for the complexation of sodium and potassium cations with 18 different crown ethers containing nitrogen atoms with different number, location and substitution pattern. The data, measured in methanol mostly with potassium salts, are compared to literature data; they show striking differences between all-oxygen analogs and the macrocycles with NH groups. In contrast, affinities with aza crown ethers bearing alkyl groups at the nitrogen as well as with the cryptand [2.2.2] come closer to the complexation free energies predicted from the number and electron donating capacity of the ligand heteroatoms. This is rationalised on the basis of molecular mechanics calculations, showing that a NH-containing crown predominates in conformations with axial N lone pairs, due to their repulsive electrostatic interactions with the ring oxygen atoms. Replacement of the hydrogen by alkyl groups forces the lone pairs to an equatorial position, thus enabling better complex formation, as borne out by experiment. In line with these arguments the IgK differences are with some exceptions more due to ΔH than to TΔS differences. The calorimetric data show linear isoequilibrium correlations between TΔS and ΔH, with slopes between those observed with other crown ether and cryptand complexes. Preliminary investigations of some synthetic macrocyclic amide precursors yield appreciable complexation only, if the two carbonyl oxygens can come in close contact with the guest cation. Computer aided molecular modelling shows that this is possible in a small 15C5-derivative, in which the polyethylenglycol cycle only serves as ring template without binding contributions from the ether oxygen atoms.

An Improved One-Step Method to Prepare Diaza-crown Ethers and the Cation Complexation Properties of 4,10-Diaza-18-Crown-6 with Two Transition Metal Ions

4,10-Diaza-15-crown-5, 4,10-diaza-18-crown-6, 4,13-diaza-21-crown-7, and 4,16-diaza-24-crown-8 were prepared by an improved method from the appropriate oligothylene glycol diiodides and diamines.The thermodynamic values of log K, ΔH and ΔS for the interaction of 4,10-diaza-18-crown-6 with Pb2+ and Ag+ were determined by a calorimetric titration method and compared with thermodynamic values for interactions of 4,13-diaza-18-crown-6 with the same cations.The thermodynamic values were found to be different for the two diaza-crown ligands. 4,10-Diaza-18-crown-6 and its 4,13-diaza-crown analog formed precipitates when treated with Co2+, Cd2+, Cu2+, and Ni2+ so that no thermodynamic data are reported for these interactions.

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.

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.

Chemistry of crown ethers XIX. Functionalized crown ethers for the solubilization of barium sulfate

The use of seawater as injection fluid in oil-producing formations often leads to blocking of the wells as a result of barium sulfate-scale formation.Macrocylic complexants specifically designed to solubilize barium sulfate efficiently into water have been synthesized and their BaSO4-solubilizing capacities have been determined.The stability of barium complexes of macrocyclic polyethers can be greatly increased by the introduction of flexible side-chains containing anionic groups.Most of newly synthesized complexants, based mainly on diaza-18-crown-6, give very stable complexes.However, many o f them are extremely insoluble in water.Only bis(carboxymethyl)diaza-18-crown-6, bis(phosphonomethyl)diaza-18-crown-6 and, to a lesser extent, bis(dicarboxymethyl)diaza-18-crown-6 and bisdiaza-18-crown-6 are efficient solubilizers of BaSO4 in water.

SYNTHESIS OF N-UNSUBSTITUTED DI- AND TRIAZA CROWN ETHERS.

Facile syntheses of di- and triaza crown ethers by intramolecular cyclization of oligoethylene glycols containing two or three imino groups or by their intermolecular cyclization with oligoethylene glycol bis(p-toluenesulfonate)s are described.

Complexes of macrocyclic compounds

Novel macrocyclic (monocyclic and bicyclic) compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cation-containing macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents.

Monocyclic macrocyclic compounds and complexes thereof

Novel monocyclic macrocyclic compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cation-containing macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents.