Quick Search
Monoamylamine (MAA) is a primary aliphatic amine that is n-pentane in which a hydrogen of one of the methyl groups is replaced by an amino group.
A water-soluble liquid with boiling point 104℃, Monoamylamine (MAA) is a strong irritant.
Clear colourless to very slightly yellow liquid.
CAS: 110-58-7
MF: C5H13N
MW: 87.16
EINECS: 203-780-2
Synonyms
PentylaMiMe;n-Amylamine,99%;n-Amylamine,97%;Amylamine, n-: (1-Pentylamine);Pentylamine, 98+%;n-Pentylamine, 98+%;1-Aminopentane, n-Amylamine;1-Aminopentane, n-Amylamine, Pentylamine
Monoamylamine (MAA) is a strong base in aqueous solutions and organic solvents that readily forms salts with acids.
A clear colorless liquid with an ammonia-like odor.
Flash point 30°F. Irritates the eyes and respiratory system.
Vapors are heavier than air.
Produces toxic oxides of nitrogen during combustion. Used as a corrosion inhibitor, solvent, flotation agent and in the manufacture of other chemicals.
Monoamylamine (MAA) is a specialty mixture of n-amylamine and 2-methylbutylamine.
A unique neutralizing agent and versatile intermediate for the synthesis of boramides, neutralized fatty acids and triazines.
Monoamylamine (MAA) is a specialty mixture of n-amylamine and 2-methylbutylamine.
A unique neutralizing agent and versatile intermediate for the synthesis of boramides, neutralized fatty acids and triazines.
Monoamylamine (MAA) Chemical Properties
Melting point: −55 °C(lit.)
Boiling point: 104 °C(lit.)
Density: 0.752 g/mL at 25 °C(lit.)
Vapor density: 3.01 (vs air)
Vapor pressure: 120.9 hPa (47 °C)
FEMA: 4242 | PENTYLAMINE
Refractive index: n20/D 1.411(lit.)
Fp: 42 °F
Storage temp.: Flammables area
Solubility: Soluble in alcohol, ether.
pka: 10.63(at 25℃)
Form: Liquid
Color: Clear colorless to very slightly yellow
Odor: at 0.10 % in propylene glycol. ammoniacal fishy
Odor Type: fishy
Biological source: synthetic
Explosive limit: 2.2-22%(V)
Water Solubility: soluble
Sensitive: Air Sensitive
JECFA Number: 1585
Merck: 14,598
BRN: 505953
Dielectric constant: 4.6（22℃）
LogP: 1.49
CAS DataBase Reference: 110-58-7(CAS DataBase Reference)
NIST Chemistry Reference: Monoamylamine (MAA)(110-58-7)
EPA Substance Registry System: Monoamylamine (MAA) (110-58-7)
Uses
Monoamylamine (MAA) is a useful reactant in organic synthesis.
Monoamylamine (MAA) is a general reagent used in functionalizing the target molecules with pentyl chain.
Monoamylamine (MAA) has also been used as a cosurfactant to increase the phase stability of the bilayer systems.
Chemical intermediate, dyestuffs, rubber chemicals, insecticides, synthetic detergents, flotation agents, corrosion inhibitors, solvent, gasoline additive, pharmaceuticals.
Industrial uses
In 1976, 800 tons of Monoamylamine (MAA) was produced for a variety of commercial purposes.
Monoamylamine (MAA) is used in textiles, lubrication and in the manufacture of dyestuffs, emulsifying agents, anti-oxidants and desizing agents for the textile and pharmaceutical industry.
Monoamylamine (MAA) is also valuable as a corrosion inhibitor and as a base for emulsifiers which are soluble in vegetable and mineral oils.
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.
Monoamylamine (MAA) was also demonstrated using inhibitors that Monoamylamine (MAA) 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.
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, Monoamylamine (MAA) was reported to inhibit rat liver monoamine oxidase in a partially irreversible and noncompetitive manner.
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 Monoamylamine (MAA) 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, Monoamylamine (MAA) had no effect on liver monoamine oxidase activity.
Several other studies strongly suggest that Monoamylamine (MAA) is a substrate for monoamine oxidase and is metabolized by this enzyme in vivo.
McEwen (1965a) purified monoamine oxidase from human plasma and found Monoamylamine (MAA) 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.
In agreement, others reported that Monoamylamine (MAA) was a good substrate for monoamine oxidase purified from dog serum.
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, Monoamylamine (MAA) 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.
These studies all indicate that Monoamylamine (MAA) is metabolized by monoamine oxidase in a variety of species.
Production Methods
Monoamylamine (MAA) 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, Monoamylamine (MAA) 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.
Reactivity Profile
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.
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.
Monoamylamine (MAA) has been reported that in humans a concentration of 0.3 mg/1 of the inhaled n-amylamine had no irritating effect.
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.
