7087-68-5 Usage
Description
N,N-Diisopropylethylamine is also known as Hunig's base and abbreviated as DIPEA or DIEA, It 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, N,N-Diisopropylethylamine is used as a base. Since the nitrogen centre is isolated by an ethyl group and the two isopropyl groups, It 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.
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. It 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 used in the enolate synthesis of ketones for application in directed cross-adol reactions.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
Diisopropylethylamine (DIPEA) is a clear, colorless to light yellow liquid, insoluble in water and easily soluble in acetone and other organic solvents.
Uses
N,N-Diisopropylethylamine is used as a base in organic reactions. Used in the preparation of (-)Gambierol a marine polycyclic ether toxin. It is also used in the synthesis of potent inhibitors of human brain memapsin, a key effector in the progression of Alzheimer’s disease.
Application
N,N-Diisopropylethylamine is an important pesticide and pharmaceutical intermediate, which can be used to synthesize anesthetics and herbicides, and can also be used as a sterically hindered amine to participate in various catalytic reactions.
Preparation
N,N-Diisopropylethylamine is used as a non-nucleophilic base in organic synthesis. It is prepared by the alkylation of diisopropylamine with diethyl sulphate. DIPEA can then be purified through distillation from potassium hydroxide if necessary.
General Description
N-Ethyldiisopropylamine (EDIA) reacts with monoactivated Michael acceptors to afford symmetrical sulfones.
Flammability and Explosibility
Highlyflammable
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 7087-68-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,0,8 and 7 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 7087-68:
(6*7)+(5*0)+(4*8)+(3*7)+(2*6)+(1*8)=115
115 % 10 = 5
So 7087-68-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H19N/c1-6-9(7(2)3)8(4)5/h7-8H,6H2,1-5H3
7087-68-5Relevant articles and documents
Method for preventing catalyst ZnCl2 from caking in diisopropylethylamine production
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Paragraph 0036-0072, (2020/08/09)
The invention discloses a method for preventing catalyst ZnCl2 from caking in diisopropylethylamine production, which takes diisopropylamine and chloroethane as raw materials, and comprises the following steps: adding ZnCl2 serving as a catalyst into the raw materials, and adding an anti-caking agent to form a reaction system; reacting the reaction system for 5-10 hours at the reaction temperatureof 150-190 DEG C and under the reaction pressure of 1.5-2.2 MPa; and carrying out alkali dissolution on the obtained reaction liquid, separating out a water phase, and carrying out atmospheric distillation on an organic phase to obtain the N,N-diisopropylethylamine serving as a product. According to the method disclosed by the invention, the catalyst is prevented from caking in the reaction, andthe product yield is high.
Electroactivated alkylation of amines with alcohols: Via both direct and indirect borrowing hydrogen mechanisms
Appiagyei, Benjamin,Bhatia, Souful,Keeney, Gabriela L.,Dolmetsch, Troy,Jackson, James E.
supporting information, p. 860 - 869 (2020/02/21)
A green, efficient N-alkylation of amines with simple alcohols has been achieved in aqueous solution via an electrochemical version of the so-called "borrowing hydrogen methodology". Catalyzed by Ru on activated carbon cloth (Ru/ACC), the reaction works well with methanol, and with primary and secondary alcohols. Alkylation can be accomplished by either of two different electrocatalytic processes: (1) in an undivided cell, alcohol (present in excess) is oxidized at the Ru/ACC anode; the aldehyde or ketone product condenses with the amine; and the resulting imine is reduced at an ACC cathode, combining with protons released by the oxidation. This process consumes stoichiometric quantities of current. (2) In a membrane-divided cell, the current-activated Ru/ACC cathode effects direct C-H activation of the alcohol; the resulting carbonyl species, either free or still surface-adsorbed, condenses with amine to form imine and is reduced as in (1). These alcohol activation processes can alkylate primary and secondary aliphatic amines, as well as ammonia itself at 25-70 °C and ambient pressure.
Mild N-Alkylation of Amines with Alcohols Catalyzed by the Acetate Ru(OAc)2(CO)(DiPPF) Complex
Figliolia, Rosario,Baldino, Salvatore,Nedden, Hans G.,Zanotti-Gerosa, Antonio,Baratta, Walter
supporting information, p. 14416 - 14419 (2017/10/07)
The acetate complex Ru(OAc)2(DiPPF) (2) obtained from Ru(OAc)2(PPh3)2 (1) and 1,1′-bis(diisopropylphosphino)ferrocene (DiPPF) reacts cleanly with formaldehyde affording Ru(OAc)2(CO)(DiPPF) (3) in high yield. The monocarbonyl complex 3 (0.4-2 mol %) efficiently catalyzes the N-alkylation of primary and secondary alkyl and aromatic amines using primary alcohols ROH (R=Et, nPr, nBu, PhCH2) under mild reaction conditions (30–100 °C) with an alcohol/amine molar ratio of 10-100. Formation of the monohydride RuH(OAc)(CO)(DiPPF) (4) has been observed by reaction of 3 with iPrOH in the presence of NEt3 at RT through an equilibrium reaction.