IUPAC Name: 3-methoxypropan-1-amine
EC / List no.: 226-241-3
Molecular Weight: 89.14
Molecular Formula: C4H11NO
3-Methoxypropylamine is a C3 amine terminated with a methoxy group. The compound is used as a corrosion inhibitor in aqueous media.
MOPA is suitable for the gentle removal of the Boc protective group and as a molecular building block for the synthesis of the dye Disperse Blue 60 and the UV filter Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate (S87), which was only recently approved in the EU.
The cyanoethylation of methanol on acrylonitrile forms almost quantitatively 3-methoxypropionitrile, which can be hydrogenated to 3-methoxypropylamine on a nickel/cobalt catalyst in the presence of excess ammonia (yield 96 %).
The addition of ammonia during the hydrogenation of the nitrile suppresses the formation of the secondary amine bis(3-methoxypropyl)amine.
3-Methoxypropylamine is a clear, colorless to yellowish liquid with an amine-like odor that is completely miscible with water. An aqueous solution (100 g·l−1) shows a pH value of 11.5 at 20 °C.
MOPA is readily soluble in a variety of organic solvents.
The substance is hygroscopic and sensitive to air.
3-Methoxypropylamine neutralizes corrosive carbon dioxide dissolved in water and, because of its good solubility in water and organic solvents, is used in functional fluids such as B. heat carriers, cooling lubricants, brake and hydraulic fluids or used in the separation of anhydrous hydrocarbon mixtures in refineries as a corrosion inhibitor.
Recently, the gentle removal of the tert-butyloxy (Boc) protecting group from functionalized heteroaromatics such as B. indoles described.
The conventional Boc cleavage in acids with z. B. trifluoroacetic acid fails in this case.
The temperature-stable disperse dye C.I. Disperse Blue 60 can be obtained by reacting bromamic acid with ammonia and sodium cyanide to form 1,4-diamino-2,3-dicyanoanthraquinone, subsequent hydrolysis to form the dicarboximide and reaction with MOPA.
Disperse Blue 60 is suitable for the blue coloring of products made from thermoplastic polymers, e.g. B. polyester fibers.
A Knoevenagel reaction of 3-methoxypropylamine with 1,3-cyclohexanedione gives rise to 1-(2-ethylhexylamino)-5,5-dimethyl-cyclohexenone-3 - from 2-ethylhexylamine with dimedone (5,5- dimethylcyclohexane-1,3-dione) – the starting compound 3-(3-methoxypropylamino)-2-cyclohexen-1-one for the latest UV absorber S87 approved by the EU in December 2020.
In the final synthesis step, the second carbonyl group of the precursor is first reacted with diethyl sulfate to form the enol ether and then with 2-ethoxyethyl cyanoacetate to form methoxypropylamino cyclohexenylidene ethoxyethyl cyanoacetate (S87) in a further Knoevenagel reaction.
Das Absorptionsmaximum λmax des in Sonnenschutzmitteln bis zu einer Konzentration von 3 % zugelassenen UV-Absorbers S87 liegt im UV-A-Bereich bei 385 nm.
Die Verbindung fällt bei der Synthese als (Z)-Isomer an und isomerisiert in Lösung innerhalb von fünf Stunden zu einem Gemisch von ca. 60 % (Z)-Isomer und ca. 40 % (E)-Isomer.
Vapor Pressure: 21.7 mm Hg
Odor Threshold Low: 0.2 ppm
Odor Threshold High: 42 ppm
Description: Colorless liquid with an ammonia-like odor
Boiling point: 116 °C
Melting point: 116 °C
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 3
Exact Mass: 89.084063974
Monoisotopic Mass: 89.084063974
Topological Polar Surface Area: 35.2 Å²
Heavy Atom Count: 6
Formal Charge: 0
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Other release to the environment of this substance is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
This substance can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones).
3-Aminopropyl methyl ether
Propanolamine methyl ether
methoxy propyl amine
3-methoxy propyl amine
3-Methoxypropylamine, analytical standard