75507-25-4

Basic information

• Product Name: 2-HYDROXYMETHYL-15-CROWN-5
• Synonyms: 1,4,7,10,13-PENTAOXACYCLOPENTADECANE-2-METHANOL;2-HYDROXYMETHYL-15-CROWN-5;2-(HYDROXYMETHYL)-15-CROWN 5-ETHER;2-(HYDROXYMETHYL)-1,4,7,10,13-PENTAOXACYCLOPENTADECAN;2-(HYDROXYMETHYL)-1,4,7,10,13-PENTAOXACYCLOPENTADECANE;1,4,7,10,13-Pentaoxacyclopentadecane-3-methanol;Hydroxy-15-crown-5;2-Hydroxymethyl-15-crown-5,96%
• CAS NO: 75507-25-4
• Molecular Formula: C₁₁H₂₂O₆
• Molecular Weight: 250.29
• EINECS: 278-222-4
• Product Categories: Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry
• Mol File: 75507-25-4.mol

Chemical Properties

• Boiling Point: 135 °C1.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 1.175 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.23E-08mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Soluble in water(58 g/L) (25°C).
• BRN: 3589706
• CAS DataBase Reference: 2-HYDROXYMETHYL-15-CROWN-5(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYMETHYL-15-CROWN-5(75507-25-4)
• EPA Substance Registry System: 2-HYDROXYMETHYL-15-CROWN-5(75507-25-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 75507-25-4(Hazardous Substances Data)

Usage

Uses

2-Hydroxymethyl-15-crown-5 is used for chemical research.

InChI:InChI=1/C11H22O6/c12-9-11-10-16-6-5-14-2-1-13-3-4-15-7-8-17-11/h11-12H,1-10H2/t11-/m1/s1

Upstream product

• 41024-91-3 penta(ethylene glycol) bis(p-toluenesulfonate) 
• 112-60-7 Tetraethylene glycol 
• 114951-76-7 1-(benzyloxymethyl) triethylene glycol 
• 638-56-2 1,11-dichloro-3,6,9-trioxaundecane 
• 37860-51-8 tetraethylene glycol di(p-toluenesulfonate) 
• 75507-17-4 benzyl 2,4,7,10,13-pentaoxacyclopentadecan-2-ylmethyl ether 
• 68167-86-2 1-allyloxymethyl-3,6,9,12,15-pentaoxacyclopentadecane 

Downstream Products

• 84131-05-5 2-<<2-<2-(2-Benzyloxyethoxy)ethoxy>ethoxy>methyl>-15-crown-5 
• 144381-50-0 sodium monoethyl 5-tert-butyl-1-(oxymethyl-15-crown-5)methylbenzenephosphonate 
• 143773-18-6 C₃₀H₄₀O₁₀ 
• 144381-56-6 sodium monoethyl 5-<(1,1-dimethyl)decyl>-2-(oxymethyl-15-crown-5)methylbenzenephosphonate 
• 143773-19-7 C₃₇H₄₄O₁₂ 
• 84130-97-2 (15-crown-5)methyl 4-nitrobenzoate 
• 87453-21-2 2-((4-nitrophenoxy)methyl)-15-crown-5 
• 1250366-65-4 C₃₀H₄₁ClO₁₀ 
• 83585-56-2 2-aminomethyl-15-crown-5 
• 87708-36-9 5-Decyl-2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-benzoic acid methyl ester 
• 87708-28-9 5-Decyl-2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-benzoic acid 

Relevant articles and documents

Bonded crown ether type adsorbent as well as preparation method and application thereof

The invention provides a bonded crown ether type adsorbent as well as a preparation method and application thereof. Based on the application of the novel bonded crown ether type adsorbent provided bythe invention in polyether refining, alkali metals in polyether can be effectively reduced, and meanwhile, the odor of polyether is reduced to the maximum extent; and the adsorbent provided by the invention has the advantages of reproducibility and strong adsorption capacity. The preparation method of the bonded crown ether type adsorbent comprises the following steps: (1) adding alkali A into a mixed solution of ethylene glycol and an organic solvent A, heating and refluxing a reaction system after the alkali A is dissolved, dropwise adding a halogenated epoxy compound into the reaction system, and obtaining an intermediate product A after a reflux reaction is finished; (2) mixing the intermediate product A with an organic solvent B, adding alkali B into the mixed solution, heating for reflux reaction, performing purifying and acidifying after the reaction is finished to obtain an intermediate product B; and (3) mixing the intermediate product B with diaryliodonium salt for reaction to generate the bonded crown ether adsorbent.

Molecular Recognition Directed Self-Assembly of Tubular Liquid Crystalline and Crystalline Supramolecular Architectures from Taper Shaped (15-Crown-5)methyl 3,4,5-Tris(p-alkyloxybenzyloxy)benzoates and (15-Crown-5-)methyl 3,4,5-Tris(p-dodecyloxy)benzoate

The syntheses and characterization of a series of (15-crown-5-)methyl 3,4,5-tris(p-alkyloxybenzyloxy)benzoates with alkyl tails of four 25, six 26, and twelve 27 carbon atoms and of (15-crown-5-)methyl 3,4,5-tris(p-dodecyloxybenzoate) 28 are described.Complexation of the crown ether endo-receptor with NaCF3SO3 destabilizes the crystalline phase of 25, 26, 27 and 28 and induces for the case of 27 and 28 the self-assembly of a supramolecular cylindral channel-like architecture which displays a thermotropic hexagonal columnar (Φh) mesophase.Most remarkably, in the crystalline phase of the complexes of 27 with NaCF3SO3 the cylindrical structure of the Φh mesophase is maintained.Characterization of these supramolecular architectures was performed by a combination of differential scanning calorimetry (DSC), thermal optical polarized microscopy, X-ray scattering and molecular modelling.A model is proposed in which a stratum of the column is formed by six molecules of 27 and 28 with the crown ether receptors residing in the column centre and the alkyl tails radiating toward the column periphery. endo-Recognition generated via the (15-crown-5)methyl receptor upon complexation, and exo-recognition provided by the tapered 3,4,5-tris(p-dodecyloxybenzyloxy)benzoate and 3,4,5-tris(p-dodecyloxy)benzoate fragments of 27 and 28 provide the driving force for the self-assembly of this cylindrical supramolecule.

Alkali-Metal Cation Recognition Induced Isomerization of Spirobenzopyrans and Spironaphthoxazins Possessing a Crown Ring as a Recognition Site: Multifunctional Artificial Receptors

Spirobenzopyrans and spironaphthoxazins possessing a monoaza-crown ring were synthesized.Isomerization of these compounds to the open colored merocyanines was induced by recognition of alkali-metal cations and the selectivity of the coloration was found to be governed by several factors: (1) the size of the crown ring, (2) the position of recognition, (3) electric properties of both the complexed cations and the merocyanine dipoles, and (4) the length of the alkyl chains connecting the spirobenzopyran units and the crown units.The spirobenzopyrans represent rationally designed multifunctional receptors for alkali-metal cations.

A CONVENIENT SYNTHESIS OF CROWN AND AZACROWN ETHERS WITH PENDANT OXIRANE GROUP

Synthesis of 4,5-epoxy-2-oxa-1-pentylcrown (I) and N-(2,3-epoxy-1-propyl)azacrown ethers (II) from accessible materials is described.

LIPOPHILIC BIS(CROWN ETHER) DERIVATIVES OF 15-CROWN-5 AND 18-CROWN-6 AS NEUTRAL CARRIERS OF ION-SELECTIVE ELECTRODES

Lipophilic bis(crown ethers) containing 15-crown-5 and 18-crown-6 rings were synthesized so as to obtain excellent neutral carriers for K+- and Cs+-selective electrodes, respectively.The K+-selective electrode based on the dodecylmethylmalonate of bis(15-crown-5), (I) (n = 1, R = Me), exhibited eminent electrode properties, proving of great practical use, while the Cs+-selective electrode of the bis(18-crown-6) derivative (I) (n = 2, R = Me) did not give results as good as expected.The electrochemical selectivities of the K+ electrode based on the dodecylmalonate of bis(15-crown-5), (I) (n = 1, R = H), and octadecanoyloxymethyl-15-crown-5 (II) are also discussed.

Neutral Ligands with Surfactant-Type Structure - Synthesis, Complexation, and Ion Transfer

New lipophilic neutral ligands which combine crown ether and podand characteristics with structural features of surfactants (cf. formulas 1-12, 16-26) were synthesized.Their complexation behaviour was studied, their solid-to-liquid and liquid-to-liquid phase transfer properties as well as their efficiency in ion transport across a liquid model membrane.Crystalline stoichiometric complexes of the cycles 2a-4a and of 3e with NaSCN, Ba(SCN)2, and BaI2 can be isolated.Among the noncyclic representatives a crystalline complex is obtained only from 11 with BaI2.The ligand 8d behaves in aqueous solution as a typical surfactant showing micelle formation and cloud point.

Enhancement of Cation Binding in Lariat Ethers Bearing a Methyl Group at the Quaternary, Pivot Carbon Atom

A number of carbon-pivot lariat ethers have been prepared and compared, with their counterparts having a methyl group bonded to the side-arm-bearing or pivot carbon.All of the compounds examined are 15-crown-5 derivatives, and in this series, the methyl lariats invariably show a higher affinity for sodium than do the nonmethylated species.The results are less consistent in the case of potassium cation which is larger than the 15-crown-5 compound's cation binding hole.The enhanced stability constant observed for sodium with the methyl lariats is attributed to reduced s ide-arm mobility or conformational changes in either the side arm or macroring.

Crown Cation Complex Effects. 20. Syntheses and Cation Binding Properties of Carbon-Pivot Lariat Ethers

In an effort devise synthetic cation binders that will mimic the behavior of naturally occuring ionophores such as valinomycin, we have prepared approximately 30 macrocyclic (crown) polyethers bearing flexible side chains attached to the macro ring at carbon.In many of these "carbon-pivot" compounds, the side chain contains one or more neutral donor groups that, if in a suitable geometrical arrangement, may provide additional solvation to the macro-ring-bound cation.Although such donors often enhanced the cation binding ability, overall, the increases in stability constants were modest.The physical resemblance and concept of "roping and tying" the cation suggest the name "lariat ethers".Syntheses of these molecules and binding by them of Na+ and K+ cations are reported and conclusions drawn about the structural requirements and cation binding efficacy of these materials.

Synthesis of Substituted Crown Ethers from Oligoethylene Glycols

A convenient synthetic method for preparing 12-crown-4, 15-crown-5, 18-crown-6, and 21-crown-7 bearing various substituents by intramolecular cyclization of the corresponding substituted oligoethylene glycols in high yields is described.Substituents include modifiable pendent groups such as phenyl and hydroxymethyl, as well as various alkyl groups.Stability constants for the new substituted crown ethers with sodium and potassium ions in methanol were determined by potentiometric titration.The absolute effect of pendent groups on stability constants was insignificant.