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294-93-9,MFCD00005103
Catalog No.:AA002Y72

294-93-9 | 12-Crown-4

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250mg
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5g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002Y72
Chemical Name:
12-Crown-4
CAS Number:
294-93-9
Molecular Formula:
C8H16O4
Molecular Weight:
176.2102
MDL Number:
MFCD00005103
SMILES:
O1CCOCCOCCOCC1
Properties
Properties
 
BP:
254.9°C at 760 mmHg  
Form:
Liquid  
MP:
16 °C(lit.)  
Refractive Index:
n20/D 1.463(lit.)  
Stability:
Air Sensitive  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
65.1  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
4  

Downstream Synthesis Route
109-99-9    294-93-9    4158-64-9   
CASUnavailable 

[1]Chen,Hong;Bartlett,RuthA.;Dias,H.V.Rasika;Olmstead,MarilynM.;Power,PhilipP.[JournaloftheAmericanChemicalSociety,1989,vol.111,#12,p.4338-4345]

[2]Bartlett,RuthA.;Power,PhilipP.[JournaloftheAmericanChemicalSociety,1987,vol.109,#21,p.6509-6510]

1132-37-2    294-93-9   
C11H9(6)LiN2*C8H16O4 

[1]AngewandteChemie,1994,vol.106,p.695-698

[1]Chen,Hong;Bartlett,RuthA.;Dias,H.V.Rasika;Olmstead,MarilynM.;Power,PhilipP.[JournaloftheAmericanChemicalSociety,1989,vol.111,#12,p.4338-4345]

[1]Tsunoda;Ozaki;Shirakata;Tamaoka;Yamamoto;Ito[TetrahedronLetters,1996,vol.37,#14,p.2463-2466]

[2]Kuo,Ping-Lin;Kawamura,Norio;Miki,Masaki;Okahara,Mitsuo[BulletinoftheChemicalSocietyofJapan,1980,vol.53,#6,p.1689-1693]

[1]Kuo,Ping-Lin;Kawamura,Norio;Miki,Masaki;Okahara,Mitsuo[BulletinoftheChemicalSocietyofJapan,1980,vol.53,#6,p.1689-1693]

Literature

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Journal: Science (New York, N.Y.) 20120810

Title: Synthesis and structural diversity of barium (N,N-dimethylamino)diboranates.

Journal: Inorganic chemistry 20120618

Title: Theoretical and experimental study on the molecular recognition of adrenaline by supramolecular complexation with crown ethers.

Journal: Computers in biology and medicine 20120401

Title: Enantioselective syntheses of (+)-sertraline and (+)-indatraline using lithiation/borylation-protodeboronation methodology.

Journal: Organic letters 20111104

Title: Chromenone 12-crown-4 substituted zinc phthalocyanine complexes: investigation of spectral, photophysical and photochemical properties.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20111015

Title: Metabolite characterization of a novel anti-cancer agent, icotinib, in humans through liquid chromatography/quadrupole time-of-flight tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20110815

Title: Infrared spectroscopy of divalent zinc and cadmium crown ether systems.

Journal: The journal of physical chemistry. A 20110602

Title: Stabilizing high-valent metal ions with a ketimide ligand set: synthesis of Mn(N=C(t)Bu2)4.

Journal: Inorganic chemistry 20110516

Title: The formal combination of three singlet biradicaloid entities to a singlet hexaradicaloid metalloid Ge14[Si(SiMe3)3]5[Li(THF)2]3 cluster.

Journal: Journal of the American Chemical Society 20110302

Title: A comparison of complexation of Li+ ion with macrocyclic ligands 15-crown-5 and 12-crown-4 in binary nitromethane-acetonitrile mixtures by using lithium-7 NMR technique and ab initio calculation.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20110101

Title: Aggregation of perfluoroctanoate salts studied by 19F NMR and DFT calculations: counterion complexation, poly(ethylene glycol) addition, and conformational effects.

Journal: Langmuir : the ACS journal of surfaces and colloids 20101116

Title: Four-coordinate iridium(I) monohydrides: reversible dinitrogen binding, bond activations, and deprotonations.

Journal: Journal of the American Chemical Society 20100707

Title: (μ-1,4,7,10-Tetra-oxacyclo-dodeca-ne)bis-[(1,4,7,10-tetra-oxacyclo-dodeca-ne)lithium] bis-(perchlorate).

Journal: Acta crystallographica. Section E, Structure reports online 20100401

Title: (1,4,7,10-Tetra-oxacyclo-dodeca-ne)(trideuteroacetonitrile)lithium perchlorate.

Journal: Acta crystallographica. Section E, Structure reports online 20100401

Title: Complexation of syndiotactic polystyrene with 12-crown-4.

Journal: Macromolecular rapid communications 20100316

Title: 7Li NMR chemical shift titration and theoretical DFT calculation studies: solvent and anion effects on second-order complexation of 12-crown-4 and 1-aza-12-crown-4 with lithium cation in several aprotic solvents.

Journal: Magnetic resonance in chemistry : MRC 20100201

Title: Exploring gas-phase ion-ionophore interactions: infrared spectroscopy of argon-tagged alkali ion-crown ether complexes.

Journal: The journal of physical chemistry. A 20100128

Title: Structures and encapsulation motifs of functional molecules probed by laser spectroscopic and theoretical methods.

Journal: Sensors (Basel, Switzerland) 20100101

Title: Recognition of Li+ by a salophen-UO2 homodimeric complex.

Journal: Inorganic chemistry 20090907

Title: Si3C2-rings: from a nonconjugated trisilacyclopentadiene to an aromatic trisilacyclopentadienide and cyclic disilenide.

Journal: Journal of the American Chemical Society 20090513

Title: Design, synthesis, characterization, and OFET properties of amphiphilic heteroleptic tris(phthalocyaninato) europium(III) complexes. The effect of crown ether hydrophilic substituents.

Journal: Inorganic chemistry 20090105

Title: Cationic crown ether complexes of germanium(II).

Journal: Angewandte Chemie (International ed. in English) 20090101

Title: Investigation of non-nucleophilic additives for the reduction of morphological anomalies in protein arrays.

Journal: Langmuir : the ACS journal of surfaces and colloids 20081118

Title: Enhancement of photocurrent generation and open circuit voltage in dye-sensitized solar cells using Li+ trapping species in the gel electrolyte.

Journal: Chemical communications (Cambridge, England) 20080307

Title: Cyclohexane as a Li+ selective ionophore.

Journal: The journal of physical chemistry. A 20070809

Title: Ligand-activated lithium-mediated zincation of N-phenylpyrrole.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

Title: The nature of the chemical bond in linear three-body systems: from i3- to mixed chalcogen/halogen and trichalcogen moieties.

Journal: Bioinorganic chemistry and applications 20070101

Title: Exploring crown ethers as shift reagents for ion mobility spectrometry.

Journal: Analytical chemistry 20061001

Title: Determination of labile trace metals with screen-printed electrode modified by a crown-ether based membrane.

Journal: Analytica chimica acta 20060728

Title: Experimental and theoretical study of the vibrational spectra of 12-crown-4-alkali metal cation complexes.

Journal: The journal of physical chemistry. A 20060720

Title: Synthesis, structure and hydrosilylation activity of neutral and cationic rare-earth metal silanolate complexes.

Journal: Dalton transactions (Cambridge, England : 2003) 20060221

Title: Crown bowl: metallocyclophane by self-assembly of 4'-pyridylmethyl-armed 12-crown-4 ethers with Ag+ ions.

Journal: Inorganic chemistry 20060206

Title: Cationic rare-earth metal trimethylsilylmethyl complexes supported by THF and 12-crown-4 ligands: synthesis and structural characterization.

Journal: Inorganic chemistry 20050919

Title: Conformational study of the structure of 12-crown-4-alkali metal cation complexes.

Journal: The journal of physical chemistry. A 20050908

Title: Experimental and theoretical study on gas-phase ion/molecule reactions of silver trimer cation, Ag3+, with 12-crown-4.

Journal: The Journal of chemical physics 20050708

Title: 1,4,7,10-tetraoxacyclododecane-triphenylmethanethiol (1/2).

Journal: Acta crystallographica. Section C, Crystal structure communications 20050701

Title: Experimental and theoretical study of the vibrational spectra of free 12-crown-4.

Journal: The journal of physical chemistry. A 20050526

Title: Conformational study of the structure of free 18-crown-6.

Journal: The journal of physical chemistry. A 20050428

Title: Ultrafast dynamics of liquid poly(ethylene glycol)s and crown ethers studied by femtosecond Raman-induced Kerr effect spectroscopy.

Journal: The journal of physical chemistry. B 20050421

Title: Controllable donor-acceptor neutral [2]rotaxanes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20041203

Title: Micro patterning of cell and protein non-adhesive plasma polymerized coatings for biochip applications.

Journal: Lab on a chip 20041201

Title: Switchable neutral bistable rotaxanes.

Journal: Journal of the American Chemical Society 20040818

Title: Li+ -induced sigma-bond metathesis: aryl for methyl exchange on boron in a methylated monocarbadodecaborate anion.

Journal: Journal of the American Chemical Society 20040407

Title: Formation of molecular radical cations of aliphatic tripeptides from their complexes with CuII(12-crown-4).

Journal: Rapid communications in mass spectrometry : RCM 20040101

Title: Comparison of theoretical and experimental data to evaluate substrate diffusional limitations for crown ether- and methyl-beta-cyclodextrin-activated serine protease subtilisin Carlsberg in tetrahydrofuran.

Journal: Biotechnology and bioengineering 20031105

Title: The remarkable ability of lithium ion to reverse the stereoselectivity in the conjugate addition of Li[BuCuI] to a chiral N-crotonyl-2-oxazolidinone.

Journal: Organic letters 20030918

Title: From 1D strands to extended molecular assemblies in the binary compounds of dithiooxamide and dithiobiurea with crown ethers.

Journal: Organic & biomolecular chemistry 20030821

Title: Effect of additives on the stereochemical integrity and reactivity of alpha-alkoxycarbonyl alkenylcopper intermediates. Optimal conditions for the synthesis of isomerically pure tetrasubstituted alkenes.

Journal: The Journal of organic chemistry 20030725

Title: Effect of structural variation within lipophilic N-(X)sulfonyl carbamoyl lariat ethers on the selectivity and efficiency of competitive alkali metal cation extraction into chloroform.

Journal: Analytical chemistry 20020501

Title: Effect of crown ethers on structure, stability, activity, and enantioselectivity of subtilisin Carlsberg in organic solvents.

Journal: Biotechnology and bioengineering 20010820

Title: DFT study of the effect of sigma-ligands on the structure of ester enolates in THF, as models of the active center in the anionic polymerization of methyl methacrylate.

Journal: Journal of the American Chemical Society 20010530

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