695-35-2

Usage

Physical state

Colorless liquid

Odor

Strong

Uses

a. Synthesis of pharmaceuticals
b. Synthesis of agrochemicals

Key intermediate in production

a. Pesticides
b. Rubber chemicals
c. Specialty chemicals

Structural characteristics

Unique structure

Reactivity

High reactivity

Applications

a. Industrial applications
b. Research applications

Safety precautions

Handle with care due to flammable and hazardous nature

InChI:InChI=1/C7H15N/c1-7-4-3-5-8(2)6-7/h7H,3-6H2,1-2H3/t7-/m0/s1

Upstream product

• 5631-71-0 1,5-dimethyl-1,2,3,4-tetrahydro-pyridine 
• 108-99-6 3-Methylpyridine 
• 77-78-1 dimethyl sulfate 
• 78190-77-9 1,2-dimethyl-2-trichloromethylpyrrolidine 
• 7664-93-9 sulfuric acid 
• 10129-51-8 1,3-dimethylpyridinium iodide 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 535-83-1 Trigonelline 
• 1690-76-2 1,3-dimethyl-2-piperidinone 
• 56-81-5 glycerol 
• 626-56-2 3-Methylpiperidine 
• 50-00-0 formaldehyd 
• 74-88-4 methyl iodide 
• 124-38-9 carbon dioxide 

Downstream Products

• 5631-71-0 1,5-dimethyl-1,2,3,4-tetrahydro-pyridine 
• 1690-76-2 1,3-dimethyl-2-piperidinone 
• 119934-45-1 1,1',5,5'-Tetramethyl-3-(2'-piperidyl)-1,4,5,6-tetrahydropyridin 
• 86917-58-0 N-methyl-5-methyl-2-piperidinone 

Relevant academic research and scientific papers

Selective synthesis of formamides, 1,2-bis(N-heterocyclic)ethanes and methylamines from cyclic amines and CO2/H2 catalyzed by an ionic liquid-Pd/C system

The reduction of CO2 with amines and H2 generally produces N-formylated or N-methylated compounds over different catalysts. Herein, we report the selective synthesis of formamides, 1,2-bis(N-heterocyclic)ethanes, and methylamines, which is achieved over an ionic liquid (IL, e.g., 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIm][BF4])-Pd/C catalytic system. By simply varying the reaction temperature, formamides and methylamines can be selectively produced, respectively, in high yields. Interestingly, 1,2-bis(N-heterocyclic)ethanes can also be obtained via the McMurry reaction of the formed formamide coupled with subsequent hydrogenation. It was found that [BMIm][BF4] can react with formamide to form a [BMIm]+-formamide adduct; thus combined with Pd/C it can catalyze McMurry coupling of formamide in the presence of H2 to afford 1,2-bis(N-heterocyclic)ethane. Moreover, Pd/C-[BMIm][BF4] can further catalyze the hydrogenolysis of 1,2-bis(N-heterocyclic)ethane to access methylamine. [BMIm][BF4]-Pd/C was tolerant to a wide substrate scope, giving the corresponding formamides, 1,2-bis(N-heterocyclic)ethanes or methylamines in moderate to high yields. This work develops a new route to produce N-methylamine and opens the way to produce 1,2-bis(N-heterocyclic)ethane from cyclic amine as well.

METHOD FOR THE SYNTHESIS OF IONIC LIQUID

PROBLEM TO BE SOLVED: To provide a method for the synthesis of high-purity ionic liquid, which suppresses a deterioration of characteristics due to the decomposition of by-products of ionic liquid as the solvent of a nonaqueous electrolyte. SOLUTION: A nonaqueous electrolyte 107 contains: an ionic fluid containing first alicyclic quaternary ammonium cations with one or more substituents, second alicyclic quaternary ammonium cations that have the same alicyclic skeleton as that of the first alicyclic quaternary ammonium cations, one of substituents attached to a nitrogen atom in the alicyclic skeleton including a halogen, and anions that attend the first alicyclic quaternary ammonium cations and the second alicyclic quaternary ammonium cations; and an alkali metal salt. The content of the second alicyclic quaternary ammonium cations in the ionic fluid is lower than or equal to 1 wt.% with respect to the unit weight of the ionic fluid, or lower than or equal to 0.8 wt.% with respect to the unit weight of the nonaqueous electrolyte. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPOandINPIT

AMMONIUM SALT, ELECTROLYTE FOR LITHIUM SECONDARY BATTERY, AND LITHIUM SECONDARY BATTERY USING THEM

PROBLEM TO BE SOLVED: To provide: ammonium salt with low viscosity; an electrolyte for a lithium secondary battery; and the lithium secondary battery. SOLUTION: This invention relates to an ammonium salt expressed by the following chemical formula (1). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Cold molten salt and storage device

One object is to provide a power storage device including an electrolyte using a room-temperature ionic liquid which includes a univalent anion and a cyclic quaternary ammonium cation having excellent reduction resistance. Another object is to provide a high-performance power storage device. A room-temperature ionic liquid which includes a cyclic quaternary ammonium cation represented by a general formula (G1) below is used for an electrolyte of a power storage device. In the general formula (G1), one or two of R1 to R5 are any of an alkyl group having 1 to 20 carbon atoms, a methoxy group, a methoxymethyl group, and a methoxyethyl group. The other three or four of R1 to R5 are hydrogen atoms. A? is a univalent imide anion, a univalent methide anion, a perfluoroalkyl sulfonic acid anion, tetrafluoroborate (BF4?), or hexafluorophosphate (PF6?).

Glycerol as a Building Block for Prochiral Aminoketone, N-Formamide, and N-Methyl Amine Synthesis

Prochiral aminoketones are key intermediates for the synthesis of optically active amino alcohols, and glycerol is one of the main biomass-based alcohols available in industry. In this work, glycerol was catalytically activated and purposefully converted with amines to generate highly valuable prochiral aminoketones, as well as N-formamides and N-methyl amines, over CuNiAlOx catalyst. The catalyst structure can be anticipated as nano-Ni species on or in CuAlOx via the formation of nano- Cu?Ni alloy particles. This concept may present a novel and valuable methodology for glycerol utilization.

N-directed aliphatic C-H borylation using borenium cation equivalents

Highly electrophilic boron cations derived from hindered amine borane complexes have been shown to undergo intramolecular aliphatic C-H borylation.

Piperidylidene derivatives of cyano-5H-dibenzo[a,d]cycloheptene

Disclosed are 1-, 2-, or 3-cyano-N-alkyl-5H-dibenzo[a,d]-cyclohepten-5-ylidene piperidine compounds having pharmaceutical utility as tranquilizers; also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when a tranquilizing effect is indicated.

Piperidylidene derivatives of carboxy-5H-dibenzo[a,d]cycloheptene

The new 1-alkyl-4-(1, 2, or 3-carboxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compounds are prepared from the corresponding 1, 2 or 3-carboxy-5H-dibenzo[a,d]cyclohepten-5-one by reaction with a Grignard reagent prepared from a 1-alkyl-4-halo piperidine to form an intermediate carbinol, or a 1, 2 or 3-carboxy-5-(1-alkyl-4-piperidyl)-5H-dibenzo[a,d]cyclohepten-5-ol which is then dehydrated to produce the desired 1-alkyl-4-(1, 2 or 3-carboxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine, or alternatively by hydrolysis of a 1-alkyl-4-(1, 2 or 3-cyano-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compound to form the corresponding 1-alkyl-4-(1, 2 or 3-carboxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compound.

1 Alkyl-4-(10:oxo or hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compounds

The new 1-alkyl-4-(10-oxo or -hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compounds are prepared from the corresponding 10-desoxy compounds having a double bond at the 10,11-position by a process involving bromination, dehydrobromination of the resulting dibromo compound, followed by enamine formation and hydrolysis to give the desired 10-oxo compound. The compounds prepared in this manner are active as antihistamines and as appetite stimulants.