N,N-Diisopropylethylamine

N,N-Diisopropylethylamine

Skeletal formula of N,N-diisopropylethylamine
Names
IUPAC name Ethyldiisopropylamine
Other names Diisopropylethylamine Hunig's base
Identifiers
CAS Number	7087-68-5 Y
ChemSpider	73565 Y
EC Number	230-392-0
Jmol 3D model	Interactive image
MeSH	N,N-diisopropylethylamine
PubChem	81531
UN number	2733
InChI InChI=1S/C8H19N/c1-6-9(7(2)3)8(4)5/h7-8H,6H2,1-5H3 Y Key: JGFZNNIVVJXRND-UHFFFAOYSA-N Y
SMILES CCN(C(C)C)C(C)C
Properties
Chemical formula	C8H19N
Molar mass	129.25 g·mol−1
Appearance	Colorless liquid
Odor	Fishy, ammoniacal
Density	0.742 g mL−1
Melting point	−50 to −46 °C (−58 to −51 °F; 223 to 227 K)
Boiling point	126.6 °C; 259.8 °F; 399.7 K
Vapor pressure	4.1 kPa (at 37.70 °C)
Refractive index (nD)	1.414
Vapor pressure	{{{value}}}
Related compounds
Related amines	Triethylamine 2,6-Di-tert-butylpyridine 1,5-Diazabicyclo(4.3.0)non-5-ene 1,8-Diazabicycloundec-7-ene
Related compounds	Triisopropylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

N,N-Diisopropylethylamine, or Hünig's base, DIPEA or DIEA, is an organic compound and an amine. It is used in organic chemistry as a base. Because the nitrogen atom is shielded by the two isopropyl groups and an ethyl group only a proton is small enough to easily fit. Like 2,2,6,6-tetramethylpiperidine, this compound is a good base but a poor nucleophile, which makes it a useful organic reagent. Hünig's base is named after the German chemist Siegfried Hünig. The compound is a colourless liquid.

Hünig's base is commercially available. It is traditionally prepared by the alkylation of diisopropylamine with diethyl sulfate. If necessary, the compound can be purified by distillation from potassium hydroxide.

Reactions

Non-nucleophilic base

Hünig's base was investigated for its use as a selective reagent in the alkylation of secondary amines to tertiary amines by alkyl halides. This organic reaction is often hampered by a quaternization reaction to the quaternary ammonium salt but this side-reaction is absent when Hünig's base is present.

The use of Hünig's base for alkylating secondary amines

Synthesis of scorpionine

Hünig's base forms a complex heterocyclic compound called scorpionine by a reaction with disulfur dichloride catalyzed by DABCO in a one-pot synthesis.

Hünig's base in the synthesis of sscorpionine