25114-81-2

Basic information

• Product Name: Hexahydro-1H-azepine-1-carbaldehyde
• Synonyms: hexahydro-1H-azepine-1-carbaldehyde
• CAS NO: 25114-81-2
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.18
• EINECS: 246-630-1
• Mol File: 25114-81-2.mol

Chemical Properties

• Boiling Point: 241.1 °C at 760 mmHg
• Flash Point: 106.4 °C
• Appearance: /
• Density: 1.043 g/cm³
• Vapor Pressure: 0.0365mmHg at 25°C
• Refractive Index: 1.533
• PKA: -0.44±0.20(Predicted)
• CAS DataBase Reference: Hexahydro-1H-azepine-1-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Hexahydro-1H-azepine-1-carbaldehyde(25114-81-2)
• EPA Substance Registry System: Hexahydro-1H-azepine-1-carbaldehyde(25114-81-2)

Safety Data

• Hazardous Substances Data: 25114-81-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Hexahydro-1H-azepine-1-carbaldehyde is used as a key intermediate in the synthesis of various drugs and agrochemicals. Its unique chemical structure allows for the development of new pharmaceutical compounds with improved therapeutic properties and reduced side effects.
Used in Perfumery Industry:
Hexahydro-1H-azepine-1-carbaldehyde is used as a building block in the creation of perfumes and fragrances. Its sweet odor contributes to the overall scent profile of various perfumes, enhancing their appeal and longevity.
Used in Flavor and Food Industry:
Hexahydro-1H-azepine-1-carbaldehyde is used as a flavoring agent in food and beverages. Its slightly sweet taste can be used to enhance the flavor of various food products, providing a pleasant taste experience for consumers.
Used in Cosmetic and Personal Care Industry:
Hexahydro-1H-azepine-1-carbaldehyde is used as a fragrance in cosmetic and personal care products. Its sweet odor can be incorporated into various formulations, adding a pleasant scent to products such as lotions, creams, and shampoos.
However, it is important to note that due to the potential health hazards and environmental impact associated with HEXA, it should be handled and used with caution in all applications. Proper safety measures and regulations should be followed to minimize any adverse effects on human health and the environment.

InChI:InChI=1/C7H13NO/c9-7-8-5-3-1-2-4-6-8/h7H,1-6H2

Upstream product

• 111-49-9 hexamethylene imine 
• 67-66-3 chloroform 
• 32978-00-0 Isopropenyl formate 
• 143-33-9 sodium cyanide 
• 134965-38-1 Hex-1-en-2-yl formate 
• 64-18-6 formic acid 
• 75-87-6 chloral 
• 67-56-1 methanol 
• 124-38-9 carbon dioxide 
• 68-12-2 N,N-dimethyl-formamide 
• 77287-34-4 formamide 
• 53678-63-0 1-((trimethylsilyl)methyl)azepane 
• 102-82-9 tributyl-amine 
• 201230-82-2 carbon monoxide 

Downstream Products

• 58570-32-4 hexahydro-1H-azepin-1-yl-chloroformiminium chloride 
• 145291-05-0 {(C₄H₂NC(C₆H₅))3(C₄HN(CH₂N(CH₂)6)C(C₆H₅))Cu} 
• 1417619-11-4 1-(4-(trifluoromethyl) phenyl) azepane 
• 56951-51-0 1-[N-(5-nitro-[1,3,4]thiadiazol-2-yl)-formimidoyl]-azepane 

Relevant articles and documents

Choline-based ionic liquids for CO2 capture and conversion

Choline-based ionic liquids (Ch-ILs) with anions possessing interacting sites to attract CO2 were designed, which could capture CO2 with capacity >1.0 mol CO2 per molar IL under ambient conditions. Moreover, this kind of ILs combining with CuCl could catalyze the formylation of amines with CO2/H2 at 120 °C. Especially, choline imidazolate showed the best performance, affording a series of N-formamides in excellent yields. It was demonstrated that the IL activated CO2 and the synergistic effect between the IL and CuCl resulted in the high activity for catalysing the formylation of amines with CO2/H2.

Synthesis method of hexahydro-1H-azepine-1-formaldehyde

The invention relates to a synthesis method of hexahydro-1H-azepine-1-formaldehyde, the synthesis method comprises the following steps: 1) reducing caprolactam to obtain hexamethyleneimine: caprolactam and a reducing agent are subjected to a reduction reaction in a solvent under the catalysis of a catalyst, and hexamethyleneimine is obtained through separation; and 2) carrying out an amidation reaction on the hexahydro-1H-azepine-1-formaldehyde and formamide to obtain hexahydro-1H-azepine-1-formaldehyde: carrying out a condensation reflux reaction on the hexahydro-1H-azepine-1-formaldehyde and the formamide under a reduced pressure condition, and purifying after the reaction is finished to obtain the hexahydro-1H-azepine-1-formaldehyde. The synthesis method adopts a decompression method, so that the use of iodobenzene diacetate and other catalysts is avoided, the production cost is reduced, the reaction selectivity is higher, the yield and the purity of the reaction product are high, the reaction condition is mild, the used solvent is easy to obtain and lower in toxicity, less three wastes are generated along with the reaction, and the pollution to the environment is smaller.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

Copper catalyzed: N-formylation of α-silyl-substituted tertiary N-alkylamines by air

A site-selective method to prepare N-formyl amines efficiently that relies on the copper(i)-catalyzed oxidation of α-silyl-substituted tertiary N-alkylamines by air at room temperature is described. The oxidative protocol was shown to exhibit excellent functional group tolerance as it was applicable to a wide variety of amine substrates and a number of bioactive molecules and natural products. Moreover, it delinates a ligand-and additive-free amine oxidation process mediated by a low-cost metal salt with oxygen from air taking on the role of both the terminal oxidant and as part of the formylation reagent, which is unprecedented in copper catalysis. It also offers the first synthetic method that can selectively generate α-amino radical species as reactive intermediates from α-silylamines under non-photochemical reaction conditions.

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 of using graphene oxide to catalyze formylation reaction to synthesize formamide derivative

The invention discloses a method of using graphene oxide to catalyze formylation reaction to synthesize a formamide derivative. The method includes: allowing amine compound and formamide compound to be in one-pot reaction under catalytic action of graphene oxide to generate the formamide derivative. Reaction raw materials and a catalyst are low in cost and easy to obtain, the catalyst can be recycled, reaction steps and operations are simple, the method has the advantages of high reaction selectivity, high yield and supportiveness of expanding reaction, and the defects that reaction reagents are high in toxicity, catalysts are expensive, the number of reaction steps is large and the number of byproducts is large in the prior art are overcome.

N-formylation of amine using graphene oxide as a sole recyclable metal-free carbocatalyst

Abstract: Graphene oxide (GO), an inexpensive, environment-friendly, and metal-free carbocatalyst, used for the N-formylation of amines is developed. In this reaction, GO shows good activity, selectivity, and recyclability. This strategy has an array of advantages, such as being metal free, without additive, wide-scope protocol, scalable with a low catalyst loading of 3?wt%, use of readily available and recyclable carbocatalyst, and DMF as a readily available formyl source. Furthermore, this strategy provides an avenue for the convenient hydroformylation of various amines. Graphical abstract: [Figure not available: see fulltext.].

Method for synthesizing formamide derivatives by molybdenum catalyzed formylation reaction

The invention discloses a method for synthesizing formamide derivatives by molybdenum catalyzed formylation reaction. The method includes that the formamide derivatives are generated by one-pot reaction of amine compounds and formamide compounds under the catalytic action of molybdenum salts and/or molybdenum oxides. Reaction methods and catalysts are cheap and easy to acquire, reaction steps andoperations are simple, the method has advantages of high reaction selectivity, high yield, expandability in reaction and the like, and defects of high toxicity of reaction agents, expensive catalysts,complex reaction steps, high quality of by-products and the like in the prior art are overcome.

Cobalt(II)-Catalyzed N-Acylation of Amines through a Transamidation Reaction

A practical protocol has been developed for a Co(OAc)2·4H2O-catalyzed transamidation reaction. The reaction gives high yields and uses N,N-dimethylformamide and other amides as carbonyl sources. The protocol is rapid and simple, and it does not require any acids, bases, ligands, or other additives. It works well for a wide range of primary, secondary, and heterocyclic amines.

Ethanol-mediated N-formylation of amines with CO2/H2 over cobalt catalysts

The CO2-involved synthesis of chemicals is of great significance from a green and sustainable point of view. Herein, we present an efficient Co-based catalytic system composed of a commercially available Co salt, the tetradentate phosphine ligand P-(CH2CH2PPh2)3, and a base, denoted as [Co]/PP3/base, for the synthesis of formamides via the formylation of amines with CO2/H2. It was indicated that the selectivity of products (i.e., formamide or methylamine) could be tuned to some extent via changing the solvent and the base. Using ethanol as the solvent, the Co(ClO4)2·6H2O/PP3/K2CO3 system showed high activity for the production of formamides, affording product yields of 82-95%, together with its broad substrate scope. Exploration of the reaction mechanism indicated that formamide was formed with HCOOH as the intermediate, while the methylamine byproduct was produced with HCHO as the intermediate via the hydrogenolysis of dialkylaminomethane.