Information about Methylamine
| Methylamine | |
|---|---|
) | |
) | |
) | |
| IUPAC name | aminomethane |
| Other names | monomethylamine MMA |
| Identifiers | |
| CAS number | |
| RTECS number | PF6300000 |
| SMILES | CN |
| Properties | |
| Molecular formula | CH5N |
| Molar mass | 31.1 g/mol |
| Appearance | Colorless Gas |
| Density | 0.902 g/cm³, 40w/w% in water |
| Melting point | -94 °C (179.15K) |
| Boiling point | -6 °C (267.2 K) |
| Solubility in water | 108 g/100 mL (20 °C) |
| Acidity (pKa) | 10.64 |
| Basicity (pKb) | 3.36 |
| Viscosity | 0.23 cP at 0 °C |
| Structure | |
| Molecular shape | tetrahedral |
| Dipole moment | 1.31 D (gas) |
| Hazards | |
| MSDS | From EMD Chemicals [1] |
| Main hazards | Corrosive liquid and gas, inhalation hazard, flammable. |
| NFPA 704 |
|
| R-phrases | 11-36/37 (40% solution in water) |
| Flash point | 8 °C |
| Related Compounds | |
| Related ? | Ammonia dimethylamine trimethylamine |
| Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) | |
)
Methylamine is the chemical compound with a formula of CH3NH2. It is a derivative of ammonia, wherein one H atom is replaced by a methyl group. It is the simplest primary amine. It is usually sold as solutions in methanol (2M), ethanol (8M), THF (2M), and water (40%), or as the anhydrous gas in pressurized metal containers. It has a strong odour similar to rotten fish. Methylamine is used both as a solvent and as a building block for the synthesis of other organic compounds. It is on the DEA watchlist for chemical precursors because of clandestine use in manufacture of the drug MDMA (ecstasy) and methamphetamine.
Chemistry
Methylamine is a good nucleophile as it is highly basic and unhindered. Its use in organic chemistry is pervasive. For example, it is a precursor to CH3NCS.[1]The hydrochloride salt of methylamine, methylammonium chloride, CH3NH3Cl, is a colourless powder that can be converted to the amine.
Production
Methylamine is prepared commercially by the reaction of ammonia with methanol with zeolite as catalyst.[2]CH3OH + NH3 → CH3NH2 + H2O
It can also be readily prepared by the reaction of hydrochloric acid with hexamine or by the reaction of formaldehyde with ammonium chloride.[3]
NH4Cl + H2CO → CH2NH·HCl + H2O
CH2NH·HCl + H2CO + H2O → CH3NH2 + HCOOH
Methylamine serves as a buffering agent in the lumen of the chloroplast in plants, effectively siphoning off protons that are heading for ATP synthase.
References
1. ^ Moore, M. L.; Crossley, F. S. "Methyl Isothiocyanate" Organic Syntheses, Coll. Vol. 3, p.599 (1955).[2]
2. ^ Corbin D.R.; Schwarz S.; Sonnichsen G.C. (1997). "Methylamines synthesis: A review". Catalysis Today 37 (2): 71-102. DOI:10.1016/S0920-5861(97)00003-5.
3. ^ Marvel, C. S.; Jenkins, R. L. "Methylamine Hydrochloride" Organic Syntheses, Collected Volume 1, p.347 (1941).[3]
2. ^ Corbin D.R.; Schwarz S.; Sonnichsen G.C. (1997). "Methylamines synthesis: A review". Catalysis Today 37 (2): 71-102. DOI:10.1016/S0920-5861(97)00003-5.
3. ^ Marvel, C. S.; Jenkins, R. L. "Methylamine Hydrochloride" Organic Syntheses, Collected Volume 1, p.347 (1941).[3]
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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smiles
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The simplified molecular input line entry specification or SMILES
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.smiType of format: chemical file format
The simplified molecular input line entry specification or SMILES
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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In physics, density is mass m per unit volume V—how heavy something is compared to its size. A small, heavy object, such as a rock or a lump of lead, is denser than a lighter object of the same size or a larger object of the same weight, such as pieces of
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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Water is a common chemical substance that is essential to all known forms of life.[1] In typical usage, water refers only to its liquid form or state, but the substance also has a solid state, ice, and a gaseous state, water vapor.
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An acid dissociation constant, denoted by Ka, is an equilibrium constant for the dissociation of a weak acid. According to the Brønsted-Lowry theory of acids and bases an acid is only recognised by its reaction with a base.
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An acid dissociation constant, denoted by Ka, is an equilibrium constant for the dissociation of a weak acid. According to the Brønsted-Lowry theory of acids and bases an acid is only recognised by its reaction with a base.
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Viscosity is a measure of the resistance of a fluid to deform under either shear stress or extensional stress. It is commonly perceived as "thickness", or resistance to flow.
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The poise (symbol P; IPA: /pwɑːz/) is the unit of dynamic viscosity in the centimetre gram second system of units. It is named after Jean Louis Marie Poiseuille.
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The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. It is defined as 10-18 statcoulomb centimeter (or 10-20 esu m). In SI units, 1 D equals 3.33564*10-30 coulomb meter. It is named after the physicist Peter J.
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Occupational safety and health (OSH) is a cross-disciplinary area concerned with protecting the safety, health and welfare of people engaged in work or employment. As a secondary effect, OSH may also protect co-workers, family members, employers, customers, suppliers, nearby
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NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. It defines the colloquial "fire diamond" used by emergency personnel to quickly and easily identify the risks posed by nearby hazardous materials.
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R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations.
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The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture in air. At this temperature the vapor may cease to burn when the source of ignition is removed.
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question mark (?), also known as an interrogation point, question point, query,[1] or eroteme, is a punctuation mark that replaces the full stop at the end of an interrogative sentence.
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Ammonia is a compound with the formula NH3. It is normally encountered as a gas with a characteristic pungent odor. Ammonia contributes significantly to the nutritional needs of the planet as a precursor to foodstuffs and fertilizers.
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Dimethylamine or N-methylmethanamine or DMA is an organic compound and an amine. It is a colorless, liquefied and flammable gas with an ammonia and fish-like odor. Dimethylamine is generally used as a solution in water at concentrations up to around 40%.
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Trimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia-like odor in higher concentrations.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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Ammonia is a compound with the formula NH3. It is normally encountered as a gas with a characteristic pungent odor. Ammonia contributes significantly to the nutritional needs of the planet as a precursor to foodstuffs and fertilizers.
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In chemistry, a methyl group is a hydrophobic alkyl functional group derived from methane (CH4). It has the formula -CH3 and is very often abbreviated as -Me in the structure of a molecule. This hydrocarbon unit can be found in many organic compounds.
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Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. Structurally amines resemble ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups.
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Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naptha or wood spirits, is a chemical compound with chemical formula CH3OH.
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Ethanol, also known as ethyl alcohol, drinking alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound, and is best known as the alcohol found in alcoholic beverages.
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