7087-68-5 Usage
Description
N,N-Diisopropylethylamine, also known as Hunig's base and abbreviated as DIPEA or DIEA, is a sterically hindered amine and an organic compound. It is a colorless liquid named after Siegfried Hunig, a German chemist. N,N-Diisopropylethylamine is commercially available and is used as a base in organic chemistry due to its ability to bind to protons. Its steric hindrance makes it a poor nucleophile, which is a blend of properties that makes it valuable as an organic reagent.
Uses
1. Used in Organic Reactions:
N,N-Diisopropylethylamine is used as a base in various organic reactions, including the palladium(0)-catalyzed alkoxycarbonylation of allyl acetates and phosphates. It serves as a neutralizer of the produced phosphoric acid, and the alkyl ester cannot be produced without DIPEA.
2. Used in Enolate Synthesis:
When combined with boryl triflates, N,N-Diisopropylethylamine is used in the enolate synthesis of ketones for application in directed cross-adol reactions.
3. Used as a Proton Scavenger:
DIPEA is applied as a proton scavenger in organic synthesis. Its steric hindrance makes it a perfect choice of a base for use with extremely reactive alkylating agents.
4. Used in Protecting Group Chemistry:
DIPEA is specifically useful as a base in the protection of alcohols as substituted ethers in the field of protecting group chemistry.
5. Used in Peptide Synthesis:
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 affect the degree of racemization.
6. Used in Pesticide and Pharmaceutical Industries:
N,N-Diisopropylethylamine is an important intermediate in the synthesis of anesthetics, herbicides, and other pharmaceuticals. It can also be used as a sterically hindered amine to participate in various catalytic reactions.
7. Used in the Preparation of (-)Gambierol:
N,N-Diisopropylethylamine is used in the preparation of (-)Gambierol, a marine polycyclic ether toxin.
8. Used in the Synthesis of Alzheimer's Disease Inhibitors:
It is also used in the synthesis of potent inhibitors of human brain memapsin, a key effector in the progression of Alzheimer's disease.
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.
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.
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.
Method for synthesis of N,N-diisopropyl ethylamine
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Paragraph 0018-0038, (2017/04/18)
The invention discloses a method for synthesis of N,N-diisopropyl ethylamine; with diisopropylamine as a reaction raw material, a quaternary ammonium salt as an ethylization reagent and alcohol as a solvent, and under a condition of the presence of an acid binding agent, N,N-diisopropyl ethylamine is synthesized; the molar ratio of the diisopropylamine to the quaternary ammonium salt is 1 to (1-2), and a refluxing reaction is performed for 3-7 hours; the obtained reaction product is postprocessed to obtain high-purity N,N-diisopropyl ethylamine. The DIPEA synthesized by the method has the advantages of simple operation, relatively high yield, simple postprocessing and the like.