2700-30-3

Usage

Uses

Used in Pharmaceutical Industry:
N,N-Diisopropylformamide is used as a catalyst for various chemical reactions in the pharmaceutical industry. Its ability to facilitate and enhance the rate of reactions makes it a valuable component in the synthesis of certain drugs and medicinal compounds.
Used in Chemical Synthesis:
In the field of chemical synthesis, N,N-Diisopropylformamide is used as a catalyst to improve the efficiency and selectivity of specific reactions. Its unique properties allow it to lower the activation energy required for a reaction to occur, thus increasing the overall yield and reducing the time needed for the process.
Used in Research and Development:
N,N-Diisopropylformamide is also utilized in research and development settings, where its chemical properties are explored for potential applications in various fields. The study of its mass spectroscopic data, retention indices, and NMR spectra contributes to the understanding of its structure and reactivity, which can lead to the discovery of new uses and applications.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C7H15NO/c1-6(2)8(5-9)7(3)4/h5-7H,1-4H3

Upstream product

• 64-18-6 formic acid 
• 108-18-9 diisopropylamine 
• 75-09-2 dichloromethane 
• 67-66-3 chloroform 
• 3424-21-3 triisopropylamine 
• 102-82-9 tributyl-amine 
• 50-00-0 formaldehyd 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 67-56-1 methanol 
• 124-38-9 carbon dioxide 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 201230-82-2 carbon monoxide 
• 17622-65-0 tert-Butylperoxymethyl-diisopropyl-amine 

Downstream Products

• 68714-10-3 (1-ethylpropyl)diisopropylamine 
• 91904-99-3 N,N-diisopropyl-N'-(phenylsulfonyl)formimidamide 
• 51804-83-2 N,N-diisopropyl-2-oxo-2-phenylacetamide 
• 3085-76-5 diisopropylcyanamide 
• 19009-39-3 N,N-diisopropylcarbamoyl chloride 
• 65367-56-8 N,N-diisopropyl-1-hydroxycyclohexanecarboxyamide 
• 65367-58-0 N,N-diisopropyl-2,3-diphenylpropanamide 
• 51804-81-0 α-hydroxy-N,N-bis(1-methylethyl)benzeneacetamide 
• 41220-69-3 N'-(4-Chloro-phenyl)-N,N-diisopropyl-formamidine 
• 121290-02-6 (E)-3-Diisopropylamino-3-phenyl-2-trifluoromethanesulfonyl-propenal 
• 10342-97-9 N,N-diisopropylmethylamine 
• 764-93-2 1-decyne 
• 112-31-2 caprinaldehyde 
• 1860-39-5 5-methylhexanal 

Relevant academic research and scientific papers

Highly productive CO2 hydrogenation to methanol-a tandem catalytic approach: Via amide intermediates

A new system for CO2 reduction to methanol has been demonstrated using homogeneous ruthenium catalysts with a range of amine auxiliaries. Modification of this amine has a profound effect on the yield and selectivity of the reaction. A TON of 8900 and TOF of 4500 h-1 is achieved using a [RuCl2(Ph2PCH2CH2NHMe)2] catalyst with a diisopropylamine auxiliary.

Additive-free selective methylation of secondary amines with formic acid over a Pd/In2O3 catalyst

Formic acid is used as the sole carbon and hydrogen source in the methylation of aromatic and aliphatic amines to methylamines. The reaction proceeds via a formylation/transfer hydrogenation pathway over a solid Pd/In2O3 catalyst without the need for any additive.

Highly Efficient and Selective N-Formylation of Amines with CO2 and H2 Catalyzed by Porous Organometallic Polymers

The valorization of carbon dioxide (CO2) to fine chemicals is one of the most promising approaches for CO2 capture and utilization. Herein we demonstrated a series of porous organometallic polymers could be employed as highly efficient and recyclable catalysts for this purpose. Synergetic effects of specific surface area, iridium content, and CO2 adsorption capability are crucial to achieve excellent selectivity and yields towards N-formylation of diverse amines with CO2 and H2 under mild reaction conditions even at 20 ppm catalyst loading. Density functional theory calculations revealed not only a redox-neutral catalytic pathway but also a new plausible mechanism with the incorporation of the key intermediate formic acid via a proton-relay process. Remarkably, a record turnover number (TON=1.58×106) was achieved in the synthesis of N,N-dimethylformamide (DMF), and the solid catalysts can be reused up to 12 runs, highlighting their practical potential in industry.

N-formylation of amines using phenylsilane and CO2 over ZnO catalyst under mild condition

Several research studies have been conducted on N-formylation of amines using phenylsilane and CO2. However, most of these studies involved tedious processes of catalyst preparation or complex procedures. In the present study, we describe the use of a simple and commercially available ZnO catalyst for selective N-formylation of amines under mild condition. High-yielding N-formylation products with good recyclability and wide substrate scope were obtained, which can promote fine chemical synthesis and CO2 capture.

A N-Phosphinoamidinato NHC-Diborene Catalyst for Hydroboration

The use of the N-phosphinoamidinato NHC-diborene catalyst 2 for hydroboration is described. The N-phosphinoamidine tBu2PN(H)C(Ph)= N(2,6-iPr2C6H3) was reacted with nBuLi in Et2O to afford the lithium derivative, which was then treated with B2Br4(SMe2)2 in toluene to form the N-phosphinoamidinate-bridged diborane 1. It was reacted with the N-heterocyclic carbene IMe (:C{N(CH3)C(CH3)}2) and excess potassium graphite at room temperature in toluene to give the N-phosphinoamidinato NHC-diborene compound 2. It can stoichiometrically activate ammonia-borane and carbon dioxide. It also showed catalytic capability. A 2 mol % portion of 2 catalyzed the hydroboration of carbon dioxide (CO2) with pinacolborane (HBpin) in deuterated benzene (C6D6) at 110 °C (conversion >99%), which afforded the methoxyborane [pinBOMe] (yield 97.8%, TOF 33.3 h-1) and the bis(boryl) oxide [(pinB)2O]. In addition, 5 mol % of 2 catalyzed the N-formylation of secondary and primary amines by carbon dioxide and pinacolborane to yield the N-formamides (average yield 91.6%, TOF 25.9 h-1). Moreover, 2 showed chemoselectivity toward catalytic hydroboration of carbonyl compounds. In mechanistic studies, the B= B double bond in compound 2 activated the substrates, the intermediates of which then underwent hydroboration with pinacolborane to yield the products and regenerate catalyst 2.

Copper-Catalyzed Formylation of Amines by using Methanol as the C1 Source

Cu/TEMPO catalyst systems are known for the selective transformation of alcohols to aldehydes, as well as for the simultaneous coupling of alcohols and amines to imines under oxidative conditions. In this study, such a Cu/TEMPO catalyst system is found to catalyze the N-formylation of a variety of amines by initial oxidative activation of methanol as the carbonyl source via formaldehyde and formation of N,O-hemiacetals and oxidation of the latter under very mild conditions. A vast range of amines, including aromatic and aliphatic, primary and secondary, and linear and cyclic amines are formylated under these conditions with good to excellent yields. Moreover, paraformaldehyde can be used instead of methanol for the N-formylation.

Tetracoordinate borates as catalysts for reductive formylation of amines with carbon dioxide

We report sodium trihydroxyaryl borates as the first robust tetracoordinate organoboron catalysts for reductive functionalization of CO2. These catalysts, easily synthesized from condensing boronic acids with metal hydroxides, activate main group element-hydrogen (E-H) bonds efficiently. In contrast to BX3 type boranes, boronic acids and metal-BAr4 salts, under transition metal-free conditions, sodium trihydroxyaryl borates exhibit high reactivity of reductive N-formylation toward a variety of amines (106 examples), including those with functional groups such as ester, olefin, hydroxyl, cyano, nitro, halogen, MeS-, ether groups, etc. The over-performance to catalyze formylation of challenging pyridyl amines affords a promising alternative method to the use of traditional formylation reagents. Mechanistic investigation supports electrostatic interactions as the key for Si/B-H activation, enabling alkali metal borates as versatile catalysts for hydroborylation, hydrosilylation, and reductive formylation/methylation of CO2.

A NHC-silyliumylidene cation for catalytic N?formylation of amines using carbon dioxide

This study describes the use of a silicon(II) complex, namely, the NHC-silyliumylidene cation complex [(IMe)2SiH]I (1, IMe =:C{N(Me)C(Me)}2), to catalyze the chemoselective N-formylation of primary and secondary amines using CO2 and PhSiH3 under mild conditions to afford the corresponding formamides as a sole product (average reaction time: 4.5 h; primary amines, average yield: 95%, average TOF: 8 h?1; secondary amines, average yield: 98%, average TOF: 17 h?1). The activity of 1 and product yields outperform the currently available non-transition-metal catalysts used for this catalysis. Mechanistic studies show that the silicon(II) center in complex 1 catalyzes the C?N bond formation via a different pathway in comparison with non-transition-metal catalysts. It sequentially activates CO2, PhSiH3, and amines, which proceeds via a dihydrogen elimination mechanism, to form formamides, siloxanes, and dihydrogen gas.

Zinc Powder Catalysed Formylation and Urealation of Amines Using CO2 as a C1 Building Block?

Transformation of CO2 into valuable organic compounds catalysed by cheap and biocompatible metal catalysts is one of important topics of current organic synthesis and catalysis. Herein, we report the zinc powder catalysed formylation and urealation of amines with CO2 and (EtO)3SiH under solvent free condition. Using 2 molpercent zinc powder as the catalyst, a series of secondary amines, both the aromatic ones and the aliphatic ones, can be formylated into formamides. When primary aromatic amines were used as the substrates, the reactions produce urea derivatives. The electronic and steric effects from the substrates on the formylation and urealation reactions were observed and discussed. The recovery and reusability of zinc powder were investigated, showing the zinc powder can be reused in the formylation reaction without loss of catalytic activity. The analysis on the reactants/products mixture after filtering out the zinc powder showed the zinc concentration in the mixture is low to 1 ppm. The pathways for the formylation and urealation of amines with this catalytic system were also investigated, and related to the different substrates.

Engineering Porphyrin Metal-Organic Framework Composites as Multifunctional Platforms for CO2Adsorption and Activation

As an effective solution toward the establishment of a sustainable society, the reductive transformation of CO2 into value-added products is certainly important and imperative. Herein, we report a porphyrin metal-organic framework composite Au@Ir-PCN-222, which is obtained through the in situ formation of Au nanoparticles in the coordination interspaces of Ir-PCN-222. Catalytic results show that Au@Ir-PCN-222 is highly efficient for CO2 reduction and aminolysis, giving rise to formamides in high yields and selectivities under room temperature and atmospheric pressure. Mechanistic studies disclose that the high efficiency of Au@Ir-PCN-222 is due to the synergistic catalysis of Au NPs and Ir-PCN-222, in which Au NPs can adsorb CO2 molecules on their surfaces and then increase the CO2 concentration in the cavities of the framework, and at the same time, Au NPs transfer electrons to Ir-porphyrin units and therefore increase the interactions with CO2 molecules.