2591-76-6

Usage

Chemical Properties

Colorless liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C9H19NO/c1-8(2)5-10(7-11)6-9(3)4/h7-9H,5-6H2,1-4H3

Upstream product

• 64-18-6 formic acid 
• 110-96-3 diisobutylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 96-26-4 dihydroxyacetone 
• 123-91-1 1,4-dioxane 
• 77287-34-4 formamide 
• 19244-89-4 N,N-diisobutyl-2-methyl-1-propen-1-ylamine 
• 2955-86-4 N¹,N¹,N²,N²-tetraisobutylethane-1,2-diamine 
• 201230-82-2 carbon monoxide 
• 67-66-3 chloroform 

Downstream Products

• 42298-81-7 diisobutyl-pent-1-enyl-amine 

Relevant academic research and scientific papers

CARBONYLATION OF AMINES CATALYZED BY ORGANOZINC COMPOUND

Dietylzinc was found to catalyze the carbonylation of amines including aromatic amines to give the corresponding formamides in good yields.

Silver-Catalyzed, N-Formylation of Amines Using Glycol Ethers

A silver-catalyzed protocol was found to afford the N-formylation of amines in moderate-to-good yields. Ethylene glycol-derived, oligomeric ethers were found to function as the formylating agent, with 1,4-dioxane affording the best results. This reaction does not require the use of stoichiometric activating reagents, and avoids the use of explosive reagents or toxic gases, such as CO, as the C1 synthon. Mechanistic studies indicate a single-electron transfer-based pathway. This work highlights the ability of silver to participate in unexpected reaction pathways.

Method for preparing N-formylated amine compounds

The invention discloses a method for preparation N-formylated amine compounds. In the method, the amine compounds and 1,3-dihydroxy acetone are taken as reaction raw materials reacting in a reactor for 2-48 hours at the reaction temperature of 0-100DEG C in a reaction medium in the presence of composite catalysts and oxidants, and the N-formylated amine compounds are obtained. The method is simpleand moderate in reaction conditions, cost can be reduced, target products can be obtained with high yield, and the catalysts used have high catalytic activity and are easy to be separated from a reaction system and reuses; the method is environment friendly during the whole process, the reaction raw materials are easy to be converted from biodiesel by-product propylene glycol, and use of glycerolis facilitated.

Preparation method of formamide compound

The invention provides a preparation method of a formamide compound. A preparation process of the preparation method comprises the following steps: uniformly mixing formic acid and an amine compound raw material selected from primary amine or secondary amine to prepare a homogeneous reaction system; raising the temperature of the homogeneous reaction system to 160 DEG C to 230 DEG C; decomposing the homogeneous reaction system to obtain carbon monoxide and enabling the carbon monoxide to participate in reaction; collecting a reaction product to obtain the formamide compound. The invention provides a novel technology for synthesizing the formamide compound through a heterogeneous method; a catalyst does not need to be used in a reaction process and an operation process is simple and controllable; the selectivity of the amine compound raw material is high.

Transamidation of carboxamides catalyzed by Fe(III) and water

The highly efficient transamidation of several primary, secondary, and tertiary amides with aliphatic and aromatic amines (primary and secondary) is described. The reaction is performed in the presence of a 5 mol % concentration of different hydrated salts of Fe(III), and the results show that the presence of water is crucial. The methodology was also applied to urea and phthalimide to demonstrate its versatility and wide substrate scope. An example of its use is an intramolecular application in the synthesis of 2,3-dihydro-5H-benzo[b]-1,4- thiazepin-4-one, which is the bicyclic core of diltiazem and structurally related drugs (Budriesi, R.; Cosimelli, B.; Ioan, P.; Carosati, E.; Ugenti, M. P.; Spisani, R. Curr. Med. Chem. 2007, 14, 279-287). A plausible mechanism that explains the role of water is proposed on the basis of experimental observations and previous mechanistic suggestions for transamidation reactions catalyzed by transition metals such as copper and aluminum. This methodology represents a significant improvement over other existing methods; it can be performed in air and with wet or technical grade solvents.

Visible light induced photocatalytic conversion of enamines into amides

A series of enamines were photocatalytically cleaved to produce amide products under simple visible-light irradiation from a 45 W household light bulb. Mechanistically, the reactions appear to involve photosensitized formation of a singlet oxygen intermediate and a subsequent [2+2] cycloaddition event. Georg Thieme Verlag Stuttgart, New York.

Visible-light photo-catalytic C-C bond cleavages: Preparations of N,N-dialkylformamides from 1,2-vicinal diamines

A range of 1,2-vicinal diamines were smoothly converted into N,N-dialkylformamides under the synergistic actions of Ru(bpy) 3Cl2 photo-catalyst, 45 W household lighting bulb, and Cs2CO3 basic additive under very mild reaction conditions. The process involves visible light-enabled photo-catalytic cleavage of C-C bond as the strategic event.

Solvent effect in the ruthenium catalyzed carbonylation of amines. Selective synthesis of dialkylformamides

Formamides are selectively produced in the ruthenium-catalyzed carbonylation of amines in alcoholic solvents.The process is shown to occur sequentially via initial carbonylation of the alcohol to yield the corresponding formate, which then reacts with the amine to yield the formamide.The method is of interest for the carbonylation of unreactive amines (aniline, t-butylamine).