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N,N-Diisopropylethylamine

Basic information Description Stability and Reactivity Applications Safety Related Supplier

N,N-Diisopropylethylamine Basic information

Product Name:
N,N-Diisopropylethylamine
CAS:
7087-68-5
MF:
C8H19N
MW:
129.24
EINECS:
230-392-0
Mol File:
7087-68-5.mol
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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
pka
10.98±0.28(Predicted)
form 
Liquid
Specific Gravity
0.755 (20/4℃)
color 
APHA: <20
PH
12.3 (H2O, 20℃)(as an emulsion)
explosive limit
0.7-6.3%(V)
Water Solubility 
miscible
BRN 
605301
InChIKey
JGFZNNIVVJXRND-UHFFFAOYSA-N
CAS DataBase Reference
7087-68-5(CAS DataBase Reference)
NIST Chemistry Reference
(i-C3H7)2(C2H5)N(7087-68-5)
EPA Substance Registry System
2-Propanamine, N-ethyl-N-(1-methylethyl)- (7087-68-5)
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Safety Information

Hazard Codes 
C,F,T
Risk Statements 
11-22-34-52/53-20/21/22-10-41-37/38-20/22-36/37/38-61
Safety Statements 
26-36/37/39-45-61-16-27-60-23-9-53
RIDADR 
UN 2734 8/PG 2
WGK Germany 
2
9-34
Autoignition Temperature
240 °C
Hazard Note 
Highly Flammable/Corrosive/Harmful
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29211980
Toxicity
LD50 orally in Rabbit: > 200 - 500 mg/kg

MSDS

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N,N-Diisopropylethylamine Usage And Synthesis

Description

Also 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 Reactivity

DIPEA 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.

Applications

N,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 Properties

Clear, colorless to light yellow liquid

Uses

It is used as a base in organic synthesis. Because the nitrogen atom

Purification Methods

Distil 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

Preparation Products

(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-DIMETHYLAMINE3-HYDROXYMETHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTERN-Boc-5,6,7,8-tetrahydro-3-methoxy-[1,2,4]triazolo[4,3-A]pyrazine ,98%2-Ethylpiperazine3-(5-METHYL-1,2,4-OXADIAZOL-3-YL)BENZALDEHYDE1-Boc-azetidine-3-ylmethanolBAPTA, TETRASODIUM SALTBAPTA3-Azetidinecarboxylic acid2-(TRIFLUOROMETHYL)THIAZOLE-5-CARBALDEHYDE4,5-Diaminopyrimidine3-(N-Boc-aminomethyl)azetidine1-Boc-3-(Aminomethyl)azetidine2-(PIPERAZIN-1-YL)-ACETIC ACID N-(2-PHENYLETHYL)-AMIDE1-Boc-3-CyanoazetidineTERT-BUTYL N-(BENZYLOXY)CARBAMATEMETHYL 2-((PIPERIDIN-4-YL)METHYL)BENZOATE2-((1-(TERT-BUTOXYCARBONYL)PIPERIDIN-4-YL)METHYL)BENZOIC ACID3-[(4-METHYLPIPERAZIN-1-YL)METHYL]BENZALDEHYDE(R)-4-Boc-Piperazine-3-carboxylic acid5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one6-CHLORO-5-NITROPYRIMIDIN-4-AMINEN-(4-FORMYL-PYRIDIN-3-YL)-2,2-DIMETHYL-PROPIONAMIDE3-((1-(TERT-BUTOXYCARBONYL)PIPERIDIN-4-YL)METHYL)BENZOIC ACID4-((1-(TERT-BUTOXYCARBONYL)PIPERIDIN-4-YL)METHYL)BENZOIC ACIDMETHYL 4-((PIPERIDIN-4-YL)METHYL)BENZOATEMETHYL 3-((PIPERIDIN-4-YL)METHYL)BENZOATEMETHYL 5-NITRO-2-FUROATE5-Amino-4,6-dichloropyrimidine4,6-Dichloro-5-nitropyrimidine4-(3-BROMOPHENYL)MORPHOLINEFaropenem sodium hemipentahydrate5-AMINO-6-CHLORO-PYRIMIDIN-4-OL4-AMINO-6-CHLOROPYRIMIDIN-5-YLAMINE4-CHLORO-6-HYDRAZINO-PYRIMIDIN-5-YLAMINE4-ETHYNYLANILINE3-Bromo-2-methoxy-propenePIPERAZINE-1,4-DICARBOXYLIC ACID TERT-BUTYL ESTER METHYL ESTER2-AMINO-5-PHENYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER
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Nanjing Apicci Pharmaceutical Technology Co., Ltd. Gold
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Alfa Aesar Gold
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Energy Chemical Gold
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021-58432009
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sales8178@energy-chemical.com
Basic information Description Stability and Reactivity Applications Safety Related Supplier