N,N-Diisopropyléthylamine

N,N-Diisopropyléthylamine

Structure de la diisopropyléthylamine
Identification
Nom UICPA N-Éthyl-N-propan-2-ylpropan-2-amine
Synonymes

DIPEA, base de Hünig, N-Éthyldiisopropylamine

No CAS 7087-68-5
No ECHA 100.027.629
No CE 230-392-0
SMILES
InChI
Propriétés chimiques
Formule C8H19N  [Isomères]
Masse molaire[1] 129,243 2 ± 0,007 9 g/mol
C 74,35 %, H 14,82 %, N 10,84 %,
Propriétés physiques
ébullition 127 °C [2]
Masse volumique 0,76 g·cm-3 à 20 °C [2]
Précautions
SGH[2]
SGH02 : InflammableSGH05 : CorrosifSGH06 : Toxique
Danger
H225, H301, H314, H412, P210, P273, P280, P301+P330+P331, P305+P351+P338 et P309+P310
Transport[2]
   3286   

Unités du SI et CNTP, sauf indication contraire.

La N, N-diisopropyléthylamine (DIPEA), également appelée base de Hünig, est un composé chimique de formule semi-développée ((CH3)2CH–)2N–CH2CH3.

C'est une amine tertiaire utilisée comme base en chimie organique. Elle est essentiellement utilisée à la place de la triéthylamine en raison de son encombrement stérique plus important autour de l'atome d'azote limitant sa nucléophilie. En effet, l'atome d'azote est lié à deux groupes isopropyle et un groupe éthyle, et seul un proton H+ est assez petit pour venir s'y lier. La DIPEA est une base organique plutôt forte, cependant faiblement nucléophile, à l'image de la 2,2,6,6-tétraméthylpipéridine, ce qui en fait un réactif organique très utile.

On la prépare traditionnellement par réaction de la diisopropylamine avec le sulfate de diéthyle[3].

Notes et références

  1. Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
  2. a b c d et e Entrée « N,N-Diisopropylethylamine » dans la base de données de produits chimiques GESTIS de la IFA (organisme allemand responsable de la sécurité et de la santé au travail) (allemand, anglais), accès le 21 juillet 2011 (JavaScript nécessaire)
  3. (de) Siegfried Hünig, Max Kiessel, « Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen », Chemische Berichte, vol. 91, no 2,‎ , p. 380-392 (lire en ligne) DOI 10.1002/cber.19580910223

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