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Diglyme information


Diglyme
Skeletal formula of diglyme
Space-filling model of the diglyme molecule
Names
Preferred IUPAC name
1-Methoxy-2-(2-methoxyethoxy)ethane[1]
Other names
Diglyme
2-Methoxyethyl ether
Di(2-methoxyethyl) ether
Diethylene glycol dimethyl ether
Identifiers
CAS Number
  • 111-96-6 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1736101
ChEBI
  • CHEBI:46784 checkY
ChEMBL
  • ChEMBL1234162
ChemSpider
  • 13839575 checkY
DrugBank
  • DB02935 checkY
ECHA InfoCard 100.003.568 Edit this at Wikidata
EC Number
  • 203-924-4
Gmelin Reference
26843
PubChem CID
  • 8150
RTECS number
  • KN3339000
UNII
  • M4BH3X0MVZ checkY
UN number 2252 1993
CompTox Dashboard (EPA)
  • DTXSID1024621 Edit this at Wikidata
InChI
  • InChI=1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 checkY
    Key: SBZXBUIDTXKZTM-UHFFFAOYSA-N checkY
  • InChI=1/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3
    Key: SBZXBUIDTXKZTM-UHFFFAOYAG
SMILES
  • COCCOCCOC
Properties
Chemical formula
(CH3OCH2CH2)2O
Molar mass 134.175 g·mol−1
Density 0.937 g/mL
Melting point −64 °C (−83 °F; 209 K)
Boiling point 162 °C (324 °F; 435 K)
Solubility in water
Miscible
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS08: Health hazard
Signal word
Danger
Hazard statements
H226, H360
Precautionary statements
P201, P202, P210, P233, P240, P241, P242, P243, P280, P281, P303+P361+P353, P308+P313, P370+P378, P403+P235, P405, P501
Flash point 57 °C (135 °F; 330 K)
Related compounds
Related compounds
Diethylene glycol diethyl ether, ethylene glycol dimethyl ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diglyme, or bis(2-methoxyethyl) ether, is an organic compound with the chemical formula (CH3OCH2CH2)2O. It is a colorless liquid with a slight ether-like odor. It is a solvent with a high boiling point. It is the dimethyl ether of diethylene glycol. The name diglyme is a portmanteau of diglycol methyl ether. It is miscible with water as well as organic solvents.

It is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst.[2]

  1. ^ Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 704. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Siegfried Rebsdat; Dieter Mayer. "Ethylene Glycol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101. ISBN 978-3527306732.

and 28 Related for: Diglyme information

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Diglyme

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Diglyme, or bis(2-methoxyethyl) ether, is an organic compound with the chemical formula (CH3OCH2CH2)2O. It is a colorless liquid with a slight ether-like...

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Triethylene glycol dimethyl ether

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Triethylene glycol dimethyl ether (also called triglyme) is a glycol ether used as a solvent. Monoglyme Diglyme Tetraglyme v t e...

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Sodium borohydride

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forms lumps. It can be purified by recrystallization from warm (50 °C) diglyme. Sodium borohydride is soluble in protic solvents such as water and lower...

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Vanadium hexacarbonyl

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typically diglyme, CH3OCH2CH2OCH2CH2OCH3. This triether solubilizes sodium salts, akin to the behavior of a crown ether: 4 Na + VCl3 + 6 CO + 2 diglyme →...

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DG

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code for Decigram, a unit of measure Dentate gyrus, a brain structure Diglyme, an organic solvent Directional gyroscope, a heading indicator use in aircraft...

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Lithium aluminium hydride

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+ LiH Potassium aluminium hydride (KAlH4) can be produced similarly in diglyme as a solvent: LiAlH4 + KH → KAlH4 + LiH The reverse, i.e., production of...

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C6H14O3

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C6H14O3 (molar mass: 134.17 g/mol, exact mass: 134.0943 u) may refer to: Diglyme Dipropylene glycol 2-(2-Ethoxyethoxy)ethanol Trimethylolpropane This set...

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Surface treatment of PTFE

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ethylene glycol dimethyl ether (monoglyme), diethylene glycol dimethyl ether (diglyme), and tetraethylene glycol dimethyl ether (tetraglyme). Glymes pose minimal...

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T2 Laboratories explosion and fire

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reactor, temperatures also increased in the reactor until the solvent (diglyme) reached decomposition temperature. The pressure and temperature continued...

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Perylene

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alkali metals to give a deeply colored radical anion and a dianion. The diglyme solvates of these salts have been characterized by X-ray crystallography...

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Diethylene glycol diethyl ether

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Other names Diethyl carbitol Bis(2-ethoxyethyl) ether Ethyl diglyme Diethyldiethylene glycol 3,6,9-Trioxaundecane Diethyldiglycol Identifiers...

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Dipotassium cyclooctatetraenide

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to brown. The structure of K2(diglyme)C8H8 has been characterized by X-ray crystallography of the derivatives with diglyme complexed to the potassium cations...

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Sodium cyanoborohydride

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in water 212 g/(100 mL) (29 °C) Solubility soluble in water, ethanol, diglyme, tetrahydrofuran, methanol slightly soluble in methanol insoluble in diethyl...

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Diborane

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48 °F; 180.66 K) Solubility in water Reacts Solubility in other solvents Diglyme and Diethyl Ether, Vapor pressure 39.5 atm (16.6 °C) Structure Coordination...

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Metal carbonyl

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as a reducing agent in chelating solvents such as diglyme. VCl3 + 4 Na + 6 CO + 2 diglyme → Na(diglyme)2[V(CO)6] + 3 NaCl [V(CO)6]− + H+ → H[V(CO)6] → 1/2 H2...

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Molybdenum hexacarbonyl

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429 K) Solubility in water insoluble Solubility slightly soluble in THF, diglyme, acetonitrile Structure Crystal structure Orthogonal Coordination geometry...

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Nitrilium

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formed can then be reduced to secondary amines with sodium borohydride in diglyme. This is a convenient route to secondary amines of the form RCH2—NH—R′...

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Trimesitylvanadium

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reduction of dinitrogen by using V(Mes)3(THF). After reducing with Na metal in diglyme, Na[V(Mes)3] is reacted with N2 to form N2-bound species V(Mes)3N2Na. This...

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Organozinc chemistry

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simple ethers. Crystal structures of the complexes Ph2Zn·glyme and Ph2Zn·diglyme". J. Organomet. Chem. 430: 1–13. doi:10.1016/0022-328X(92)80090-K. Lu,...

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Hydrogen storage

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by Ashby et al. by one-step synthesis in toluene, tetrahydrofuran, and diglyme. Concerning the hydrogen absorption and desorption properties, this alanate...

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Magnesocene

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without a catalyst present. Attempts to substitute THF with diethyl ether, diglyme, or benzene resulted only in polymerization of cyclopentadiene. The syntheses...

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Cyclopentadienylmolybdenum tricarbonyl dimer

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Mo(CO)3(CH3CN)3 instead of Mo(CO)6. Thermolysis of this compound in hot solution of diglyme (bis(2-methoxyethyl)ether) results in decarbonylation, giving the tetracarbonyl...

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Transition metal ether complex

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chelating ether ligands include the glymes, dimethoxyethane (dme) and diglyme, and the crown ethers. Being lipophilic, metal-ether complexes often exhibit...

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Diphenylzinc

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simple ethers. Crystal structures of the complexes Ph2Zn·glyme and Ph2Zn·diglyme". J. Organomet. Chem. 430: 1–13. doi:10.1016/0022-328X(92)80090-K. Pelletier...

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Germyl

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Liquids that have been used as solvents include liquid ammonia, ethyl amine, diglyme, or hexamethylphosphoramide. The choice of solvent depends on the temperature...

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Lutetium compounds

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Ether-Stabilized Lu(CH 2 SiMe 3 ) 3 . Molecular Structure of Lu(CH 2 SiMe 3 ) 3 (THF)(diglyme)". Zeitschrift für Naturforschung B. 60 (5): 533–537. doi:10.1515/znb-2005-0509...

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Carbones

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methylidebis-(triphenylphosphonium) bromide with potassium metal suspended in a diglyme solution, the potassium reduced the starting material to form...

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Lithium tetrahydridogallate

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Lithium tetrahydridogallate can also be dissolved in tetrahydrofuran and diglyme. Lithium tetrahydridogallate slowly decomposes at room temperature. The...

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