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D125806

Sigma-Aldrich

N,N-Diisopropylethylamine

ReagentPlus®, ≥99%

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Synonym(s):
N-Ethyldiisopropylamine, DIPEA, Ethyldiisopropylamine, ‘Hünig’s base’
Linear Formula:
[(CH3)2CH]2NC2H5
CAS Number:
7087-68-5
Molecular Weight:
129.24
EC Number:
230-392-0
MDL number:
MFCD00008868
UNSPSC Code:
12352100
PubChem Substance ID:
329798682
NACRES:
NA.21

vapor pressure

31 mmHg ( 37.7 °C)

Quality Level

200

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

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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

WGK

WGK 2

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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The Journal of Organic Chemistry, 59, 695-695 (1994)
The Journal of Organic Chemistry, 58, 7162-7162 (1993)
Synthetic Communications, 23, 3073-3073 (1993)
The Journal of Organic Chemistry, 58, 1538-1538 (1993)
Asymmetric Hydrogenation of α,β-Unsaturated Nitriles with Base-Activated Iridium N, P Ligand Complexes
Muller MA and Pfaltz A.
Angewandte Chemie (International Edition in English), 126(33), 8812-8815 (2014)
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