766-09-6

Basic information

• Product Name: 1-Ethylpiperidine
• Synonyms: 1-ethvlpiperidine;1-Ethylpiperidene;1-Ethylpiperidin;1-ethyl-piperidin;Ethylpiperidylamnie;N-Aethylpiperidin;1-ETHYLPIPERIDINE;N-ETHYLPIPERIDINE
• CAS NO: 766-09-6
• Molecular Formula: C₇H₁₅N
• Molecular Weight: 113.2
• EINECS: 212-161-6
• Product Categories: Piperidine;Building Blocks;Heterocyclic Building Blocks;Piperidines;Building Blocks;C5 to C7;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 766-09-6.mol

Chemical Properties

• Melting Point: -20 °C
• Boiling Point: 131 °C(lit.)
• Flash Point: 66 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.824 g/mL at 25 °C(lit.)
• Vapor Pressure: 12.1mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Storage Temp.: Flammables area
• Solubility: 1-ethylpiperidine salt of benzylpenicillin is considerably less
• PKA: 10.45(at 23℃)
• Explosive Limit: 1.9-12.1%(V)
• Water Solubility: 50 G/L
• BRN: 102643
• CAS DataBase Reference: 1-Ethylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethylpiperidine(766-09-6)
• EPA Substance Registry System: 1-Ethylpiperidine(766-09-6)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 2386 3/PG 2
• WGK Germany: 1
• RTECS: TN0250000
• F: 10-23
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 766-09-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Ethylpiperidine is used as a reactant for the synthesis of multiprotected kanosamine, which is an important intermediate in the development of pharmaceutical compounds.
Used in Chemical Synthesis:
1-Ethylpiperidine serves as a reagent for selective acylation in peptide synthesis, enabling the creation of specific peptide structures with desired properties.
Used in Organic Chemistry:
1-Ethylpiperidine is utilized in stereoselective aldol condensation reactions for the synthesis of β-lactam antibiotics, which are essential in the treatment of bacterial infections.
Used in Diastereoselective Synthesis:
1-Ethylpiperidine is employed in the diastereoselective synthesis of aldols, which are crucial in the development of various organic compounds with specific stereochemistry.
Used in Crossed Claisen Ester Condensation:
1-Ethylpiperidine is used as a reagent in crossed Claisen ester condensation reactions, which are important for the synthesis of complex organic molecules.
Used in Intermolecular Radical Additions:
1-Ethylpiperidine is used in the mediation of intermolecular radical additions to 2, 4, 6-trichlorophenyl vinyl sulfonate, contributing to the synthesis of various organic compounds.
Used in Room Temperature Phosphorescence:
1-Ethylpiperidine is employed in the room temperature phosphorescence of α-bromonaphthalene induced by cyclodextrin, with its application in the synthesis of 5-Bromopyrimidine, yielding up to 37%.
Used as a Solvent:
Due to its properties, 1-Ethylpiperidine is also used as a solvent in various chemical processes and for the production of other chemicals.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 5, p. 575, 1973The Journal of Organic Chemistry, 28, p. 3259, 1963 DOI: 10.1021/jo01046a537

Reactivity Profile

1-Ethylpiperidine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Highlyflammable

Safety Profile

Poison by intravenous and subcutaneous routes. An eye irritant. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits toxic fumes of Nox.

InChI:InChI=1/C7H15N/c1-2-8-6-4-3-5-7-8/h2-7H2,1H3/p+1

Upstream product

• 110-89-4 piperidine 
• 74-96-4 ethyl bromide 
• 64-17-5 ethanol 
• 74-85-1 ethene 
• 75-03-6 ethyl iodide 
• 75-07-0 acetaldehyde 
• 110-86-1 pyridine 
• 3010-03-5 piperidin-1-yl-acetonitrile 
• 75-16-1 methylmagnesium bromide 
• 618-42-8 1-piperidin-1-yl-ethanone 
• 25115-65-5 N-Ethylglutarimid 
• 725692-83-1 5-ethylamino-valeronitrile 
• 111-24-0 1,5-dibromo-pentane 
• 75-04-7 ethylamine 

Downstream Products

• 638-10-8 ethyl 3-methylbut-2-enoate 
• 1617-19-2 3-methyl-but-3-enoic acid ethyl ester 
• 13979-28-7 ethyl 2,3-dimethylbut-2-enoate 
• 14387-99-6 ethyl 2,3-dimethyl-3-butenoate 
• 102207-40-9 1,1'-(1,4-phenylene-bis(methylene))bis(1-ethylpiperidinium) dibromide 
• 17606-70-1 (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one 
• 76357-18-1 methyl 1-tritylaziridine-2-carboxylate 
• 7770-50-5 N-benzyloxycarbonylglycylglycylglycylglycine 
• 13515-90-7 N-(N-benzyloxycarbonyl-glycyl)-thiophenylalanine S-phenyl ester 
• 108759-06-4 trichloro-(ξ-2-piperidino-vinyl)-[1,4]benzoquinone 
• 78278-63-4 4-[(N-benzyloxycarbonyl-glycyl)-amino]-benzoic acid 
• 102081-88-9 [(S)-2-oxo-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-carbamic acid benzyl ester 
• 6273-61-6 1-ethyl-1-phenacyl-piperidinium; bromide 
• 6273-46-7 1-ethyl-1-(4-chloro-phenacyl)-piperidinium; bromide 

Relevant articles and documents

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

SUPPORTED HETEROGENEOUS CATALYST, PREPARATION AND USE THEREOF

A supported heterogeneous catalyst comprises rhodium and vanadium on a support, wherein the supported heterogeneous catalyst is preparable by depositing vanadium on a supported rhodium catalyst by impregnation. A process for preparing the aforementioned catalyst and a process for converting an amide into an amine in the presence of the aforementioned catalyst are provided.

PROCESS FOR CONVERTING AMIDE TO AMINE

Provided is a process for converting an amide into an amine comprising hydrogenation of the amide at a temperature not higher than 130°C and a hydrogen pressure not higher than 50 bar in the presence of a supported heterogeneous catalyst preparable by a method comprising depositing vanadium on a supported noble metal catalyst by impregnation.

Method for catalytically synthesizing 1-substituted pyrrolidine/piperidine derivative by using supported metal

The invention provides a method for catalytically synthesizing a 1-substituted pyrrolidine/piperidine derivative by using a supported metal. The method comprises: carrying out a reaction with ammoniato form a pyrrolidine ring/piperidine ring by using a supported metal as a catalyst, using 1,4-butanediol/1, 5-pentanediol as a cyclization raw material and using alcohol as an N-alkylation raw material, wherein the high-selectivity synthesis of the 1-substituted pyrrolidine/piperidine derivative is achieved through the one-step reaction, the active components of the supported metal catalyst are Cu, Ni and Pd/Ru, the total loading capacity of the active components Cu and Ni is 3-15 wt% of the carrier, and the loading capacity of Pd/Ru is 0-1 wt% of the carrier. According to the invention, themethod is simple, low in cost and environmentally friendly, the conversion rate of 1,4-butanediol/1,5-pentanediol is high, the selectivity of the pyrrolidine/piperidine derivatives is high, and the method is a production route with practical application value.

Microwave-assisted nucleophilic degradation of organophosphorus pesticides in propylene carbonate

Propylene carbonate is becoming a suitable green alternative to volatile organic solvents in the study of chemical reactions. In this study, an efficient method for nucleophilic degradation of five organophosphorus pesticides, fenitrothion, malathion, diazinon, parathion, and paraoxon, using propylene carbonate as a solvent is proposed. The effect of changing the nature of the nucleophile and the influence of microwave (MW) heating were investigated. A screening of temperatures (50 °C-120 °C) was performed under microwave heating. The pesticide degradation was followed by 31P NMR, and the extent of conversion (%) was calculated by the integration of phosphorus signals. Keeping in mind that recently it has been reported that some ionic liquids play a nucleophilic role, in this work we report for the first time the degradation of organophosphorus pesticides by using an amino acid-based ionic liquid such as Bmim[Ala] as a nucleophile and a bio-based solvent (propylene carbonate) as a reaction medium in combination with microwave heating. This journal is

A BEt3-Base catalyst for amide reduction with silane

Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt3 and base. The scope of these BEt3-base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers' silane Si-H···B activation mode wherein the hydride abstraction by BEt3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center.

A BEt3-Base Catalyst for Amide Reduction with Silane

Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt3 and base. The scope of these BEt3-base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers' silane Si-H···B activation mode wherein the hydride abstraction by BEt3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center.

Catalytic Homogeneous Hydrogenation of CO to Methanol via Formamide

A novel amine-assisted route for low temperature homogeneous hydrogenation of CO to methanol is described. The reaction proceeds through the formation of formamide intermediates. The first amine carbonylation part is catalyzed by K3PO4. Subsequently, the formamides are hydrogenated in situ to methanol in the presence of a commercially available ruthenium pincer complex as a catalyst. Under optimized reaction conditions, CO (up to 10 bar) was directly converted to methanol in high yield and selectivity in the presence of H2 (70 bar) and diethylenetriamine. A maximum TON of 539 was achieved using the catalyst Ru-Macho-BH. The high yield, selectivity, and TONs obtained for methanol production at low reaction temperature (145 °C) could make this process an attractive alternative over the traditional high temperature heterogeneous catalysis.

Mild Hydrogenation of Amides to Amines over a Platinum-Vanadium Bimetallic Catalyst

Hydrogenation of amides to amines is an important reaction, but the need for high temperatures and H2 pressures is a problem. Catalysts that are effective under mild reaction conditions, that is, lower than 30 bar H2 and 70 °C, have not yet been reported. Here, the mild hydrogenation of amides was achieved for the first time by using a Pt-V bimetallic catalyst. Amide hydrogenation, at either 1 bar H2 at 70 °C or 5 bar H2 at room temperature was achieved using the bimetallic catalyst. The mild reaction conditions enable highly selective hydrogenation of various amides to the corresponding amines, while inhibiting arene hydrogenation. Catalyst characterization showed that the origin of the catalytic activity for the bimetallic catalyst is the oxophilic V-decorated Pt nanoparticles, which are 2 nm in diameter.

Rhenium-Loaded TiO2: A Highly Versatile and Chemoselective Catalyst for the Hydrogenation of Carboxylic Acid Derivatives and the N-Methylation of Amines Using H2 and CO2

Herein, we report a heterogeneous TiO2-supported Re catalyst (Re/TiO2) that promotes various selective hydrogenation reactions, which includes the hydrogenation of esters to alcohols, the hydrogenation of amides to amines, and the N-methylation of amines, by using H2 and CO2. Initially, Re/TiO2 was evaluated in the context of the selective hydrogenation of 3-phenylpropionic acid methyl ester to afford 3-phenylpropanol (pH2 =5 MPa, =5 MPa, T=180 °C), which revealed a superior performance over other catalysts that we tested in this study. In contrast to other typical heterogeneous catalysts, hydrogenation reactions with Re/TiO2 did not produce dearomatized byproducts. DFT studies suggested that the high selectivity for the formation of alcohols in favor of the hydrogenation of aromatic rings is ascribed to the higher affinity of Re towards the COOCH3 group than to the benzene ring. Moreover, Re/TiO2 showed a wide substrate scope for the hydrogenation reaction (19 examples). Subsequently, this Re/TiO2 catalyst was applied to the hydrogenation of amides, the N-methylation of amines, and the N-alkylation of amines with carboxylic acids or esters.