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ChemicalBook >  Product Catalog >  Organic Chemistry >  Amides >  Acyclic polyamines and their derivatives >  N,N-Diisopropylethylamine

N,N-Diisopropylethylamine

Basic information Description Stability and Reactivity Applications Safety Related Supplier
N,N-Diisopropylethylamine Basic information
N,N-Diisopropylethylamine Chemical Properties
  • Melting point:-46 °C
  • Boiling point:127 °C
  • Density 0.782
  • vapor pressure 31 mmHg ( 37.7 °C)
  • refractive index n20/D 1.457
  • Flash point:6 °C
  • storage temp. Store in dark!
  • solubility miscible
  • form Liquid
  • pka10.98±0.28(Predicted)
  • Specific Gravity0.755 (20/4℃)
  • color APHA: <20
  • PH12.3 (H2O, 20℃)(as an emulsion)
  • explosive limit0.7-6.3%(V)
  • Water Solubility miscible
  • BRN 605301
  • InChIKeyJGFZNNIVVJXRND-UHFFFAOYSA-N
  • CAS DataBase Reference7087-68-5(CAS DataBase Reference)
  • NIST Chemistry Reference(i-C3H7)2(C2H5)N(7087-68-5)
  • EPA Substance Registry System2-Propanamine, N-ethyl-N-(1-methylethyl)- (7087-68-5)
Safety Information
MSDS
N,N-Diisopropylethylamine Usage And Synthesis
  • DescriptionAlso known as Hunig’s base and abbreviated as DIPEA or DIEA, N,N-Diisopropylethylamine is a sterically hindered amine and an organic compound. The colourless liquid was named as Hung’s base after Siegfried Hunig, a German chemist. It is noteworthy that the compound is commercially available.
    In organic chemistry, the compound is used as a base. Since the nitrogen centre is isolated by an ethyl group and the two isopropyl groups, N,N-Diisopropylethylamine can bind to protons. The compound is, therefore, a base similar to 2,2,6,6-tetramethylpiperidine, but a poor nucleophile, a blend of properties that makes it valuable as an organic reagent.
    Traditionally, DIPEA is prepared by the alkylation of diisopropylamine with diethyl sulphate. DIPEA can then be purified through distillation from potassium hydroxide if necessary.
  • Stability and ReactivityDIPEA exhibits violent reaction as well as flammability with nitrates, oxidizing agents, and peroxides.
    It can also react very exothermically and possibility of spitting with halogens and strong acids. In an alkaline environment, the compound is likely to react violently. In addition, the compound can form toxic products such as n-nitrosamines when combined with nitrous acid as well as oxygen, nitrosating agents, and nitrates.
    Under normal conditions (temperature and pressure), DIPEA is very stable. However, it is soluble in most organic solvents.
  • ApplicationsN,N-Diisopropylethylamine is utilized as a base in the palladium(0)catalysed alkoxycarbonylation of both allyl acetates and phosphates . When treated with triphenyphosphine in the presence of DIPEA in ethanol under carbon monoxide pressure, diethyl-2-hexenyl phosphate produces mixtures of cisand trans--ethyl heptenoates in a ratio of 84:16. DIPEA is used as a neutralizer of the produced phosphoric acid. Notably, the alkyl ester cannot be produced without DIPEA.
    When combined with boryl triflates, N,N-Diisopropylethylamine is hugely used in the enolate synthesis of ketones for application in directed cross-adol reactions . When reacted with Di-n-butylboryl Trifluoromethanesulfonate and DIPEA in ether, 4-methyl-2-pentanone generates unisolated baron enolate.
    DIPEA is applied as a proton scavenger in organic synthesis. Since the compound is a sterically hindered amine, it lacks quaternization; therefore, making it a perfect choice of a base for use with extremely reactive alkylating agents. DIPEA is specifically useful as a base in the protection of alcohols as substituted ethers in the field of protecting group chemistry.
    In the synthesis of peptides, the compound is also used in the coupling of amino acids. The steric nature and basicity of DIPEA during the coupling reaction affects the degree of racemization.
  • Chemical PropertiesClear, colorless to light yellow liquid
  • UsesIt is used as a base in organic synthesis. Because the nitrogen atom
  • Purification MethodsDistil the amine from ninhydrin, then from KOH [Dryland & Sheppard, J Chem Soc, Faraday Trans 1 125 1986]. It is a strong base and should be stored in the absence of carbon dioxide. [Hünig & Kiessel Chem Ber 91 380, 387 1958, Wotiz et al. J Org Chem 24 1202 1959, Beilstein 4 IV 551.]
N,N-Diisopropylethylamine Preparation Products And Raw materials
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