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D125806

Sigma-Aldrich

N,N-Diisopropylethylamine

ReagentPlus®, ≥99%

Synonym(s):

N-Ethyldiisopropylamine, DIPEA, Ethyldiisopropylamine, ‘Hünig’s base’

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About This Item

Linear Formula:
[(CH3)2CH]2NC2H5
CAS Number:
Molecular Weight:
129.24
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

vapor pressure

31 mmHg ( 37.7 °C)

Quality Level

product line

ReagentPlus®

Assay

≥99%

form

liquid

refractive index

n20/D 1.414 (lit.)

bp

127 °C (lit.)

mp

<−50 °C (lit.)

density

0.742 g/mL at 25 °C (lit.)

SMILES string

CCN(C(C)C)C(C)C

InChI

1S/C8H19N/c1-6-9(7(2)3)8(4)5/h7-8H,6H2,1-5H3

InChI key

JGFZNNIVVJXRND-UHFFFAOYSA-N

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General description

N,N-Diisopropylethylamine, also known as Hünig′s base, is a sterically hindered amine. It is a non-nucleophilic base commonly employed for substitution reactions. It acts as an activator for chiral iridium N, P ligand complexes, which can be utilized in the hydrogenation of α, β-unsaturated nitriles. The influence of varying concentration of N,N-diisopropylethylamine on the synthesis of olvanil in the presence of lipase catalyst has been investigated.

Application

N,N-Diisopropylethylamine may be used in the synthesis of mannosylated ovalbumin peptides.
Proton scavenger used in peptide coupling, enolboration, Pd(0)-catalyzed alkoxycarbonylation of allyl phosphates and acetates, and as a catalyst in vinyl sulfone synthesis.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

49.1 °F

Flash Point(C)

9.5 °C


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Synthetic Communications, 23, 3073-3073 (1993)
The Journal of Organic Chemistry, 58, 7162-7162 (1993)
The Journal of Organic Chemistry, 58, 1538-1538 (1993)
The Journal of Organic Chemistry, 59, 695-695 (1994)
Lipase-catalysed synthesis of olvanil in organic solvents.
Reyes-Duarte D, et al.
Biotechnology Letters, 24(24), 2057-2061 (2002)

Articles

Amide bonds are ubiquitous in both nature and industrial applications. They are vital to the structure and function of biological macromolecules and polymers. The importance of this functionality has resulted in numerous approaches to its formation, ranging from stoichiometric activation of carboxylic acids to more recent advances in catalytic amide bond formation.

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