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Monomethyl adipate

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Monomethyl adipate Basic information
Monomethyl adipate Chemical Properties
  • Melting point:7-9 °C (lit.)
  • Boiling point:162 °C/10 mmHg (lit.)
  • Density 1.081 g/mL at 25 °C (lit.)
  • refractive index n20/D 1.441(lit.)
  • Flash point:>230 °F
  • storage temp. Sealed in dry,Room Temperature
  • form Liquid
  • pka4.69±0.10(Predicted)
  • color Clear colorless
  • Water Solubility Not miscible or difficult to mix with water.
  • BRN 1766411
  • CAS DataBase Reference627-91-8(CAS DataBase Reference)
  • NIST Chemistry ReferenceHexanedioic acid, monomethyl ester(627-91-8)
  • EPA Substance Registry SystemMonomethyl adipate (627-91-8)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38
  • Safety Statements 24/25-36-26
  • WGK Germany 3
  • TSCA Yes
  • HS Code 29171290
Monomethyl adipate Usage And Synthesis
  • Chemical Propertiesclear colorless liquid
  • UsesMonomethyl Adipate is a useful synthetic intermediate. It can be used to prepare 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors which show potential antitumor activities. It can be also used to synthesize mannose-linked biphenylylacetic acid derivatives as novel inhibitors of selectin-mediated cell adhesion.
  • DefinitionChEBI: A dicarboxylic acid monoester that is the monomethyl ester of adipic acid.
  • Chemical SynthesisAccording to the general procedure described above, a has been synthesized from adipic acid (730mg, 5 mmol) and methanol (10 ml). Yield: 80%.
    1H NMR (400.1 MHz, CDCl3): δ = 8.48 (1H, br, H1), 3.40 (3H, s, H9), 2.10 (4H, m, H3-H6), 1.40(4H, m, H4-H5).
    13C NMR (100.5 MHz, CDCl3): δ = 177.6 (C2), 173.7 (C7), 51.0 (C9), 32.90 (C3), 32.87 (C6), 23.6(C5), 23.5 (C4).
    The English name of Monomethyl adipate is: Adipic acid monoethyl ester; Molecular formula is: C 8H 14O 4Molecular weight is: 174.2.It at room temperature is white in color or the red crystalline solid of micro mist.Fusing point: 28~29 ℃, boiling point: 285 ℃ (760mmHg), refractive index: n 20 D1.4390, relative density: 0.986.Water insoluble, be soluble in the organic solvents such as alcohol, ether.Monomethyl adipate and derivative thereof have widely purposes as the important organic intermediate of a class in technical field of medicine synthesis.
    The synthetic method of Monomethyl adipate mainly contains following three kinds:
    The one, under alkaline condition or issue the first portion hydrolysis reaction in the catalysis of bioactive enzyme (pork liver lipase etc.) and obtain Monomethyl adipate (such as document Blaise; Koehler; Bulletin de la Societe Chimique deFrance; Vol. (4) 7; (1910); P.219).
    The 2nd, by hexanodioic acid or adipic anhydride and ethanol, as catalyzer, the control reaction conditions carries out esterification and obtains Monomethyl adipate (such as document Chem.Zentralbl. with acid; Vol.97; (1926; P.126));
    The 3rd, by the people such as Swann nineteen forty-three with hexanodioic acid, diethylene adipate and ethanol with the condition of acid as catalyst under control reaction conditions obtain monomethyl adipate(document such as Swann; Oehler; Buswell; Org.synth.Coll.Vol.11; (1943); P.227).
    Synthetic method of monomethyl adipate
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