chemistry

Methylamine

Methylamine is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Methylamine rather than just read about it. In short: Methylamine, also known as methanamine, is an organic compound with a formula of CH5N or CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group.

Key takeaways

Methylamine belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Methylamine to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Methylamine from memory before moving on to harder problems.

Reference excerpt

Methylamine, also known as methanamine, is an organic compound with a formula of CH5N or CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold dissolved in solution with methanol, ethanol, tetrahydrofuran, or water, or as the anhydrous gas in pressurized metal containers. Industrially, methylamine is transported in its anhydrous form in pressurized railcars and tank trailers. It has a strong odor similar to rotten fish. Methylamine is used as a building block for the synthesis of numerous other commercially available compounds.

Production

Industrial production Methylamine has been produced industrially since the 1920s (originally by Commercial Solvents Corporation for dehairing of animal skins). This was made possible by Kazimierz Smoleński and his wife Eugenia who discovered amination of alcohols, including methanol, on alumina or kaolin catalyst after WWI, filed two patent applications in 1919 and published an article in 1921. It is now prepared commercially by the reaction of ammonia with methanol in the presence of an aluminosilicate catalyst. Dimethylamine and trimethylamine are co-produced; the reaction kinetics and reactant ratios determine the ratio of the three products. The product most favored by the reaction kinetics is trimethylamine.

CH3OH + NH3 → CH3NH2 + H2O In this way, an estimated 115,000 tons were produced in 2005.

Laboratory methods Methylamine was first prepared in 1849 by Charles-Adolphe Wurtz via the hydrolysis of methyl isocyanate and related compounds. An example of this process includes the use of the Hofmann rearrangement, to yield methylamine from acetamide and bromine. In the laboratory, methylamine hydrochloride is readily prepared by various other methods. One method entails treating formaldehyde with ammonium chloride.

[NH4]Cl + CH2O → [CH2=NH2]Cl + H2O [CH2=NH2]Cl + CH2O + H2O → [CH3NH3]Cl + HCOOH The colorless hydrochloride salt can be converted to an amine by the addition of a strong base, such as sodium hydroxide (NaOH):

[CH3NH3]Cl + NaOH → CH3NH2 + NaCl + H2O Another method entails reducing nitromethane with zinc and hydrochloric acid. Another method of methylamine production is spontaneous decarboxylation of glycine with a strong base in water.

Biosynthesis Methylamine arises as a result of putrefaction and is a substrate for methanogenesis. Additionally, methylamine is produced during PADI4-dependent arginine demethylation.

Reactivity and applications Methylamine is a good nucleophile as it is an unhindered amine. As an amine it is considered a weak base. Its use in organic chemistry is pervasive. Some reactions involving simple reagents include: with phosgene to methyl isocyanate, with carbon disulfide and sodium hydroxide to the sodium methyldithiocarbamate, with chloroform and base to methyl isocyanide and with ethylene oxide to methylethanolamines. Liquid methylamine has solvent properties analogous to those of liquid ammonia. Representative commercially significant chemicals produced from methylamine include the pharmaceuticals ephedrine and theophylline, the pesticides carbofuran, carbaryl, and metham sodium, and the solvents N-methylformamide and N-methylpyrrolidone. The preparation of some surfactants and photographic developers require methylamine as a building block.

Safety The LD50 (mouse, s.c.) is 2.5 g/kg. The Occupational Safety and Health Administration (OSHA) and National Institute for Occupational Safety and Health (NIOSH) have set occupational exposure limits at 10 ppm or 12 mg/m3 over an eight-hour time-weighted average.

Regulation In the United States, methylamine is controlled as a List 1 precursor chemical by the Drug Enforcement Administration due to its use in the illicit production of methamphetamine.

In popular culture Fictional characters Walter White and Jesse Pinkman use aqueous methylamine as part of a process to synthesize methamphetamine in the AMC series Breaking Bad.

Illustrations

Worked examples

Example 1 — a first encounter with Methylamine

Start with the simplest possible case. Write down what Methylamine claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Methylamine before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Methylamine ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Methylamine

In research: Methylamine appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Methylamine in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Methylamine is common in secondary-school and first-year university syllabi. It links to neighbouring topics 1849 introductions, Alkylamines, Foul-smelling chemicals, so understanding it makes those chapters shorter.
In everyday life: Look for Methylamine outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Methylamine in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Methylamine means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Methylamine out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Methylamine in simple terms?

Why does Methylamine matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Methylamine?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Methylamine.