DPE, 1,2-Diphenoxyethan

  • CAS:104-66-5
  • MF:
  • Purity:98.5%
  • Molecular Weight:
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Product Details

  • CAS: 104-66-5
  • Appearance: White Powder
  • Purity: 98.5%
  • Buy Quality Wholesale DPE 104-66-5 with Low Price

    • Molecular Formula:C14H14O2
    • Molecular Weight:214.264
    • Appearance/Colour:Off-white crystals 
    • Vapor Pressure:0.000158mmHg at 25°C 
    • Melting Point:94-96 °C(lit.) 
    • Refractive Index:1.556 
    • Boiling Point:341.555 °C at 760 mmHg 
    • Flash Point:139.355 °C 
    • PSA:18.46000 
    • Density:1.08 g/cm3 
    • LogP:3.14440 

    DPE (Cas 104-66-5) Usage

    Chemical Properties

    Off-white Crystals

    Uses

    Diphenoxyethane (DPE), also known as 1,2-diphenoxyethane, ethylene glycol diphenyl ether, 2-phenoxyethoxybenzene, and ethane, 1,2-diphenoxy-, can be used as a heat-sensitive material sensitizer and as a potential additive to polyolefin catalysts.

    Preparation

    DPE is as follows:A three-necked flask was charged with 15.7 g of bromobenzene (100 mmol) and 47 ml of DMF, and stirred. 12.7 g of sodium carbonate (120 mmol, 1.2 eq.), 1.9 g of cuprous iodide (10 mmol, 0.1 eq.), 1.87 g of 2,2'-bipyridine (12 mmol, 0.1 eq.) and 7.4 g of ethylene glycol (120 mmol, 1.2 equivalent), the reaction mixture was stirred at 100 ° C overnight. After recovering DMF under reduced pressure, 100 ml of water and 100 ml of toluene were added, and the aqueous phase was extracted three times with 300 ml of toluene, and the organic layers were combined. Washed sequentially with 5% sodium carbonate. The organic phase was dried over anhydrous sodium sulfate, filtered, and then filtered and evaporated,The crude product was recrystallized from isopropanol and dried in vacuo to give 19.5 g of product, yield 91%, purity over 99%.

    General Description

    DPE is an intermediate that forms during the sonochemical oxidation of chlorophenol and phenoxyacetic acid. DPE (C6H5–O–CH2–CH2–O–C6H5, DPOE) is a flexible bichromophore in which the two phenyl rings are separated from one another by an −O–CH2–CH2–O– chain with five flexible dihedral angles about which hindered rotation can occur. As such, it is a phenyl capped analog of dimethoxyethane (DMOE), which has served as a model compound for development of force fields for polyethylene glycol (PEG).

    Flammability and Explosibility

    Nonflammable

    Consumer Uses

    ECHA has no public registered data indicating whether or in which chemical products the substance might be used. Other release to the environment of this substance is likely to occur from: indoor use as processing aid.

    InChI:InChI=1/C14H14O2/c1-3-7-13(8-4-1)15-11-12-16-14-9-5-2-6-10-14/h1-10H,11-12H2

    104-66-5 Relevant articles

    Structural changes of 1,2-diphenoxyethane upon electronic excitation from a combined Franck-Condon/rotational constants fit

    Jascha Martini a , Marie-Luise Hebestreit a , Christian Henrichs a , Daniel Krügler b , Michael Schmitt a

    , Journal of Molecular Structure Volume 1270 , 15 December 2022, 133896

    The geometry changes of the tgt- and the ttt-rotamer of 1,2-diphenoxyethane were determined from a combined fit of line intensities in fluorescence emission spectra, obtained via pumping different vibronic transition, and the changes of rotational constants upon electronic excitation, which were taken from [E.G. Buchanan, P.S. Walsh, D.F. Plusquellic, T.S. Zwier, J. Chem. Phys. 138 (2013) 204313]. The so determined geometry changes are compared to the results of ab initio spin-component-scaled approximate coupled cluster singles and doubles (SCS-CC2) calculations.

    Inter- and Intramolecular Aryl–Aryl Interactions in Partially Fluorinated Ethylenedioxy-bridged Bisarenes**

    Weddeling, Jan-Henrik,Vishnevskiy, Yury V.,Neumann, Beate,Stammler, Hans-Georg,Mitzel, Norbert W.

    , p. 16111 - 16121 (2020)

    Several ethylenedioxy-bridged bisarenes ...

    Magnesiation of electron-rich aryl bromides and their use in nickel-catalyzed cross-coupling reactions

    Lau, Stephen Y. W.,Hughes, Greg,O'Shea, Paul D.,Davies, Ian W.

    , p. 2239 - 2242 (2007)

    Electron-rich aryl bromides are rapidly ...

    Thermo-sensitive paper sensitizer ethylene glycol diphenyl ether preparation method

    -

    Paragraph 0030; 0031, (2019/08/03)

    The invention relates to a thermo-sensit...

    Ground State Conformational Preferences and CH Stretch–Bend Coupling in a Model Alkoxy Chain: 1,2-Diphenoxyethane

    Evan G. Buchanan†Edwin L. Sibert, III*‡Timothy S. Zwier*†

    J. Phys. Chem. A 2013, 117, 13, 2800–2811

    The presence of the oxygen atoms in the chain shifts the CH scissor overtones to higher frequencies than in pure alkyl chains, qualitatively changing the spectral consequences of the Fermi resonance, with the scissor overtones now appearing as the highest frequency bands in the spectrum. The spectra are contrasted with those in 1,2-diphenylethane, a close analog with a very different appearance to its CH stretch spectrum, in which the scissor overtones appear as the lowest frequency bands.

    104-66-5 Process route

    sodium phenoxide
    139-02-6

    sodium phenoxide

    ethylene dibromide
    106-93-4

    ethylene dibromide

    1,2-diphenoxyethane
    104-66-5

    1,2-diphenoxyethane

    phenoxyethyl bromide
    589-10-6

    phenoxyethyl bromide

    Conditions
    Conditions Yield
    With ethanol;
     
    ethanol
    64-17-5

    ethanol

    ethylene dibromide
    106-93-4

    ethylene dibromide

    phenol
    108-95-2,27073-41-2

    phenol

    1,2-diphenoxyethane
    104-66-5

    1,2-diphenoxyethane

    phenoxyethyl bromide
    589-10-6

    phenoxyethyl bromide

    Conditions
    Conditions Yield
    Reaktion von Natriumphenolat;
     

    104-66-5 Upstream products

    • 100-67-4
      100-67-4

      potassium phenolate

    • 139-02-6
      139-02-6

      sodium phenoxide

    • 107-06-2
      107-06-2

      1,2-dichloro-ethane

    • 64-17-5
      64-17-5

      ethanol

    104-66-5 Downstream products

    • 51-28-5
      51-28-5

      2,4-Dinitrophenol

    • 14467-69-7
      14467-69-7

      1,2-bis(4-nitrophenoxy)ethane

    • 34074-28-7
      34074-28-7

      1,2-bis(4-formylphenoxy)ethane

    • 36506-46-4
      36506-46-4

      4,4'-(ethylenedioxy)dibromobenzene

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