110-58-7 Usage
Description
Amylamine, also known as 1-pentylamine, is a clear colorless liquid with an ammonia-like odor. It is a strong base in aqueous solutions and organic solvents, readily forming salts with acids. Amylamine is characterized by its chemical properties, which include being a colorless to slightly yellow liquid with a fishy aroma. It is used in various industries due to its versatile applications.
Uses
Amylamine is used as a chemical intermediate for the synthesis of various compounds, including dyestuffs, rubber chemicals, and pharmaceuticals. It serves as a reactant in organic synthesis, contributing to the production of different chemical products.
Used in Textile Industry:
Amylamine is used as a lubricant, emulsifying agent, and desizing agent in the textile industry. It helps improve the quality and processing of textiles by providing necessary lubrication and facilitating the emulsification of oils and other substances.
Used in Pharmaceutical Industry:
Amylamine is used as a general reagent for functionalizing target molecules with a pentyl chain, which is essential in the development of various pharmaceutical products.
Used in Corrosion Inhibition:
Amylamine is used as a corrosion inhibitor, protecting materials from the damaging effects of corrosion and extending their lifespan.
Used in Solvent Applications:
Amylamine is used as a solvent in various chemical processes, thanks to its ability to dissolve a wide range of substances.
Used in Flotation Agents:
Amylamine is used in the mining industry as a flotation agent, aiding in the separation of valuable minerals from waste materials.
Used in Insecticides:
Amylamine is used in the production of insecticides, helping to control and eliminate pests in agricultural and other settings.
Used in Synthetic Detergents:
Amylamine is used in the formulation of synthetic detergents, enhancing their cleaning properties and effectiveness.
Used in Gasoline Additives:
Amylamine is used as an additive in the gasoline industry, improving the performance and efficiency of fuel.
Production Methods
n-Amylamine is primarily produced by the amination of alkyl halides rather than
using alcohol. This reaction is carried out at a temperature of 300-500°C and a
pressure of 790-3550 kPa. Alternatively, n-amylamine can be produced from the
reaction of amyl chlorides with ammonia. This procedure also produces small
amounts of amylenes and amyl alcohol which can be removed by steam distillation
(Schweizer et al 1978).
Air & Water Reactions
Highly flammable. Less dense than water and soluble in water.
Reactivity Profile
AMYLAMINES are amines. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Can react with oxidizing materials. [NTP 1992].
Hazard
Flammable, dangerous fire risk. Strong irritant.
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.
Health Hazard
Direct skin contact with amylamine leads to first- and second-degree burns.
Inhalation results in irritation of the mucous membranes of the nose and respiratory
tract. It has been reported that in humans a concentration of 0.3 mg/1 of the
inhaled n-amylamine had no irritating effect (Loit and Filou 1964).
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.
Safety Profile
Poison by intraperitoneal route. A corrosive. A flammable liquid. When heated to decomposition it emits toxic vapors of NOx.
Metabolism
As exposure to n-amylamine is often via inhalation, several studies have investigated the uptake and distribution of amylamine by lungs. For a number of aliphatic amines their uptake correlated well with their partition coefficients (between n-octanol and pH 7 buffer) (Fowler et al 1976). The amino group, as well as the relatively lipophilic alkyl group, was required for lung specificity. It was also demonstrated using inhibitors that n-amylamine was rapidly metabolized to CO2 by monoamine oxidase and that CO2 exhalation increased with increasing chain length from C4 to C13. Another study on the pharmacokinetics of n-amylamine uptake by lung demonstrated that the distribution of n-amylamine between vascular and extravascular spaces was sensitive to arterial pH, with alkalosis favoring extravascular distribution (Effros and Chihard 1969). The ability of n-amylamine to serve as a substrate or an inhibitor of monoamine oxidase has been addressed in a number of in vitro and in vivo studies. However, many of the results are contradictory and appear to be related to concentrationdependent phenomena. When tested in vitro, n-amylamine was reported to inhibit rat liver monoamine oxidase in a partially irreversible and noncompetitive manner (Takagi and Gomi 1966). Longer chain aliphatic amines were even more inhibitory. In contrast, at lower concentrations n-amylamine served as a substrate for monoamine oxidase. Weiner (1966) also concluded that n-amylamine was a poor substrate for monoamine oxidase isolated from rat, mouse, dog, cat, and human brains. The amine was more active towards rabbit brain monoamine oxidase. When administered intraperitoneally to rats, n-amylamine had no effect on liver monoamine oxidase activity (Valiev 1974).
Several other studies strongly suggest that amylamine is a substrate for monoamine oxidase and is metabolized by this enzyme in vivo. McEwen (1965a) purified monoamine oxidase from human plasma and found it to be most active against several simple aliphatic amines, with butylamine being the most active substrate. Further characterization indicated that high concentrations of the amine inhibited the enzyme and that the non-ionized forms of the amines are responsible for the observed competitive inhibition (McEwen 1965b). In agreement, others reported that n-amylamine was a good substrate for monoamine oxidase purified from dog serum (Ikeno et al 1978). In another in vitro study, Kurosawa (1974) demonstrated n-amylamine to be a substrate for monoamine oxidase prepared from beef or rat liver. In vivo, it was found that, in rats, the release of 14CO2 from 14C-amylamine was significantly decreased by riboflavin or iron deficiency, conditions which also decreased monoamine oxidase activity (Sourkes and Missala 1976). These studies all indicate that amylamine is metabolized by monoamine oxidase in a variety of species.
Purification Methods
Dry it by prolonged shaking with NaOH pellets, then distilling. Store it in a CO2-free atmosphere. [Beilstein 4 IV 674.]
Check Digit Verification of cas no
The CAS Registry Mumber 110-58-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 110-58:
(5*1)+(4*1)+(3*0)+(2*5)+(1*8)=27
27 % 10 = 7
So 110-58-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H13N/c1-2-3-4-5-6/h2-6H2,1H3/p+1
110-58-7Relevant articles and documents
Synergism between Ni and W in the Ni-W/C sulfide catalyst in hydrodenitrogenation of pyridine and hydrodesulfurization of thiophene
Gulkova, Daniela,Zdrazil, Miroslav
, p. 735 - 746 (1999)
Parallel hydrodenitrogenation (HDN) of pyridine and hydrodesulfurization (HDS) of thiophene was studied over active-carbon-supported Ni, W, and Ni-W sulfide catalysts at 2 MPa and at 280 and 320 °C. Synergism between Ni and W was observed both in HDN and HDS reactions: the activity of the Ni-W catalyst was higher than the sum of the activities of the Ni and W catalysts. However, the synergistic increase in activity was much higher in HDS than in HDN. This led to a characteristic shift in the HDN/HDS selectivity, which was strongly shifted to the HDS side over the Ni-W catalysts as compared with the Ni and W catalysts. HDS was faster than HDN over the Ni-W catalyst, the rate of both reactions being about the same over the Ni catalyst and HDN being faster than HDS over the W catalyst. The selectivity of all the catalysts was shifted to the HDN side with decreasing temperature. The data are a new example for generalisation of the rule that the synergism in activity of bimetallic sulfide Co-Mo, Ni-Mo, and Ni-W catalysts is higher in HDS than in hydrogenation and HDN.
-
Cowen
, p. 287,291 (1955)
-
Hydrogenation of Aliphatic Nitriles to Primary Amines over a Bimetallic Catalyst Ni25.38Co18.21/MgO–0.75Al2O3 Under Atmospheric Pressure
Shi, Dongxu,Zhu, He,Han, Yaping,Zhang, Yuecheng,Zhao, Jiquan
, p. 2784 - 2794 (2021)
Abstract: A mixed oxide supported bimetallic catalyst Ni25.38Co18.21/MgO–0.75Al2O3 was readily prepared and found to be efficient in the hydrogenation of valeronitrile (VN) to amylamine (AA) under atmospheric pressure. Under the optimal conditions: H2 to VN molar ratio of 4:1, NH3 to VN molar ratio of 3:1, reaction temperature of 130?°C and residence time of 5?s, the conversion of VN reached 100% with a AA yield of 70.8%, and a diamylamine (DAA) yield of 25.9%. This catalyst was also active in the hydrogenation of other low carbon aliphatic nitriles to their corresponding primary amines. The characterization results revealed that the catalyst had the properties of large surface area, uniform and fine dispersion of metal particles in the form of Ni/Co alloy with synergy effect between the two metals, which endowed the catalyst with good catalytic performances in the hydrogenation reaction of aliphatic nitriles. Graphic Abstract: [Figure not available: see fulltext.]
-
Suter,Moffett
, p. 487 (1934)
-
Adhesive functionalized ascorbic acid on CoFe2O4: A core-shell nanomagnetic heterostructure for the synthesis of aldoximes and amines
Sorkhabi, Serve,Ghadermazi, Mohammad,Mozafari, Roya
, p. 41336 - 41352 (2020)
This paper reports on the simple synthesis of novel green magnetic nanoparticles (MNPs) with effective catalytic properties and reusability. These heterogeneous nanocatalysts were prepared by the anchoring of Co and V on the surface of CoFe2O4 nanoparticles coated with ascorbic acid (AA) as a green linker. The prepared nanocatalysts have been identified by scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, X-ray atomic mapping, thermogravimetric analysis, X-ray powder diffraction, vibrating sample magnetometer analysis, coupled plasma optical emission spectrometry and Fourier transform infrared spectroscopy. The impact of CoFe2O4@AA-M (Co, V) was carefully examined for NH2OH·HCl oximation of aldehyde derivatives first and then for the reduction of diverse nitro compounds with sodium borohydride (NaBH4) to the corresponding amines under green conditions. The catalytic efficiency of magnetic CoFe2O4@AA-M (Co, V) nanocatalysts was investigated in production of different aldoximes and amines with high turnover numbers (TON) and turnover frequencies (TOF) through oximation and reduction reactions respectively. Furthermore, the developed environment-friendly method offers a number of advantages such as high turnover frequency, mild reaction conditions, high activity, simple procedure, low cost and easy isolation of the products from the reaction mixture by an external magnetic field and the catalyst can be reused for several consecutive runs without any remarkable decrease in catalytic efficiency.
Asymmetric synthesis of serinol-monoesters catalyzed by amine transaminases
Costa, Ingrid C.R.,de Souza, Rodrigo Octavio M.A.,Bornscheuer, Uwe T.
, p. 1183 - 1187 (2017)
The asymmetric synthesis of serinol-derivatives was investigated employing different amine transaminases as biocatalysts. Under the optimized conditions conversions up to 92% and excellent enantiomeric excesses up to 99% ee were obtained providing access
Synthesis of Chiral Amines via a Bi-Enzymatic Cascade Using an Ene-Reductase and Amine Dehydrogenase
Fossey-Jouenne, Aurélie,Jongkind, Ewald P. J.,Mayol, Ombeline,Paul, Caroline E.,Vergne-Vaxelaire, Carine,Zaparucha, Anne
, (2021/12/23)
Access to chiral amines with more than one stereocentre remains challenging, although an increasing number of methods are emerging. Here we developed a proof-of-concept bi-enzymatic cascade, consisting of an ene reductase and amine dehydrogenase (AmDH), to afford chiral diastereomerically enriched amines in one pot. The asymmetric reduction of unsaturated ketones and aldehydes by ene reductases from the Old Yellow Enzyme family (OYE) was adapted to reaction conditions for the reductive amination by amine dehydrogenases. By studying the substrate profiles of both reported biocatalysts, thirteen unsaturated carbonyl substrates were assayed against the best duo OYE/AmDH. Low (5 %) to high (97 %) conversion rates were obtained with enantiomeric and diastereomeric excess of up to 99 %. We expect our established bi-enzymatic cascade to allow access to chiral amines with both high enantiomeric and diastereomeric excess from varying alkene substrates depending on the combination of enzymes.
One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis
Coeck, Robin,De Vos, Dirk E.
supporting information, p. 5105 - 5114 (2020/08/25)
The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).
