Names | |||
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Pronunciation | /ˌmɛθələˈmiːn/ (METH-ə-lə-MEEN), /ˌmɛθəˈlæmən/ (METH-ə-LA-mən), /məˈθɪləˌmiːn/ (mə-THIL-ə-meen) [1] | ||
Preferred IUPAC name Methanamine [2] | |||
Other names
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Identifiers | |||
3D model (JSmol) | |||
3DMet | |||
Abbreviations | MMA | ||
741851 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.000.746 | ||
EC Number |
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145 | |||
KEGG | |||
MeSH | methylamine | ||
PubChem CID | |||
RTECS number |
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UNII | |||
UN number | 1061 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
CH3NH2 | |||
Molar mass | 31.058 g·mol−1 | ||
Appearance | Colorless gas | ||
Odor | Fishy, ammoniacal | ||
Density | 0.6562 g/cm3 (at 25 °C) | ||
Melting point | −93.10 °C; −135.58 °F; 180.05 K | ||
Boiling point | −6.6 to −6.0 °C; 20.0 to 21.1 °F; 266.5 to 267.1 K | ||
1008 g/L (at 20 °C) | |||
log P | −0.472 | ||
Vapor pressure | 186.10 kPa (at 20 °C) | ||
Henry's law constant (kH) | 1.4 mmol/(Pa·kg) | ||
Acidity (pKa) | 10.66 | ||
Conjugate acid | [CH3NH3]+ (Methylammonium) | ||
-27.0·10−6 cm3/mol | |||
Viscosity | 230 μPa·s (at 0 °C) | ||
1.31 D | |||
Thermochemistry | |||
Std enthalpy of formation (ΔfH⦵298) | −23.5 kJ/mol | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H220, H315, H318, H332, H335 | |||
P210, P261, P280, P305+P351+P338, P410+P403 | |||
NFPA 704 (fire diamond) | |||
Flash point | −10 °C; 14 °F; 263 K (liquid, gas is extremely flammable) [3] | ||
430 °C (806 °F; 703 K) | |||
Explosive limits | 4.9–20.7% | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 100 mg/kg (oral, rat) | ||
LC50 (median concentration) | 1860 ppm (mouse, 2 hr) [3] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 10 ppm (12 mg/m3) [3] | ||
REL (Recommended) | TWA 10 ppm (12 mg/m3) [3] | ||
IDLH (Immediate danger) | 100 ppm [3] | ||
Safety data sheet (SDS) | emdchemicals.com | ||
Related compounds | |||
Related alkanamines | ethylamine, dimethylamine, trimethylamine | ||
Related compounds | ammonia | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Methylamine is an organic compound with a formula of 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 as a solution in 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.
Methylamine is 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. [4]
In this way, an estimated 115,000 tons were produced in 2005. [5]
Methylamine was first prepared in 1849 by Charles-Adolphe Wurtz via the hydrolysis of methyl isocyanate and related compounds. [5] [6] An example of this process includes the use of the Hofmann rearrangement, to yield methylamine from acetamide and bromine. [7] [8]
In the laboratory, methylamine hydrochloride is readily prepared by various other methods. One method entails treating formaldehyde with ammonium chloride. [9]
The colorless hydrochloride salt can be converted to an amine by the addition of a strong base, such as sodium hydroxide (NaOH):
Another method entails reducing nitromethane with zinc and hydrochloric acid. [10]
Another method of methylamine production is spontaneous decarboxylation of glycine with a strong base in water.[ citation needed ]
Methylamine is a good nucleophile as it is an unhindered amine. [11] 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. [12]
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. [5]
Methylamine arises as a result of putrefaction and is a substrate for methanogenesis. [13]
Additionally, methylamine is produced during PADI4-dependent arginine demethylation. [14]
The LD50 (mouse, s.c.) is 2.5 g/kg. [15]
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. [16]
In the United States, methylamine is controlled as a List 1 precursor chemical by the Drug Enforcement Administration [17] due to its use in the illicit production of methamphetamine. [18]
Fictional characters Walter White and Jesse Pinkman use methylamine as part of a process to synthesize methamphetamine in the AMC series Breaking Bad . [19] [20]
In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.
Phosgene is an organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of carbonic acid, or structurally as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics.
In organic chemistry, isocyanate is the functional group with the formula R−N=C=O. Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyanates are manufactured for the production of polyurethanes, a class of polymers.
Hydrazine is an inorganic compound with the chemical formula N2H4. It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly toxic unless handled in solution as, for example, hydrazine hydrate.
Methyl isocyanate (MIC) is an organic compound with the molecular formula CH3NCO. Synonyms are isocyanatomethane and methyl carbylamine. Methyl isocyanate is an intermediate chemical in the production of carbamate pesticides (such as carbaryl, carbofuran, methomyl, and aldicarb). It has also been used in the production of rubbers and adhesives. As an extremely toxic and irritating compound, it is very hazardous to human health. MIC was the principal toxicant involved in the Bhopal gas disaster, which eventually killed around 20,000 people in total as per official figures. It is also a very potent lachrymatory agent.
Ethylene oxide is an organic compound with the formula C2H4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of a silver catalyst.
Cyclopropene is an organic compound with the formula C3H4. It is the simplest cycloalkene. Because the ring is highly strained, cyclopropene is difficult to prepare and highly reactive. This colorless gas has been the subject for many fundamental studies of bonding and reactivity. It does not occur naturally, but derivatives are known in some fatty acids. Derivatives of cyclopropene are used commercially to control ripening of some fruit.
Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, and in the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers. Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life.
The Hofmann rearrangement is the organic reaction of a primary amide to a primary amine with one less carbon atom. The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate. The reaction can form a wide range of products, including alkyl and aryl amines.
Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a trimethylated derivative of ammonia. TMA is widely used in industry. At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes on contact. At lower concentrations, it has a "fishy" odor, the odor associated with rotting fish.
In organic chemistry, a hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: −C(OH)(NR2)−. R can be hydrogen or an alkyl group. Hemiaminals are intermediates in imine formation from an amine and a carbonyl by alkylimino-de-oxo-bisubstitution. Hemiaminals can be viewed as a blend of aminals and geminal diol. They are a special case of amino alcohols.
Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed in organic synthesis, usually as a base.
Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).
Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis.
Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.
Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).
The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with cyanide in the presence of ammonia. The condensation reaction yields an α-aminonitrile, which is subsequently hydrolyzed to give the desired amino acid. The method is used for the commercial production of racemic methionine from methional.
Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.
In organic chemistry, an ortho ester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula RC(OR′)3. Orthoesters may be considered as products of exhaustive alkylation of unstable orthocarboxylic acids and it is from these that the name 'ortho ester' is derived. An example is ethyl orthoacetate, CH3C(OCH2CH3)3, more correctly known as 1,1,1-triethoxyethane.
1-Methylimidazole or N-methylimidazole is an aromatic heterocyclic organic compound with the formula CH3C3H3N2. It is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids. It is a fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine.
...an unhindered amine such as methylamine