WordNet
- a methyl with the hydrogen atom replaced by an amino radical
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/16 12:45:08」(JST)
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| Names | |||
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| IUPAC name
aminomethane, methanamine
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Other names
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| Identifiers | |||
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CAS Number
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74-89-5 Y | ||
| 3DMet | B00060 | ||
| Abbreviations | MMA | ||
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Beilstein Reference
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741851 | ||
| ChEBI | CHEBI:16830 N | ||
| ChEMBL | ChEMBL43280 Y | ||
| ChemSpider | 6089 Y | ||
| DrugBank | DB01828 N | ||
| EC Number | 200-820-0 | ||
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Gmelin Reference
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145 | ||
| Jmol 3D model | Interactive image | ||
| KEGG | C00218 Y | ||
| MeSH | methylamine | ||
| PubChem | 6329 | ||
| RTECS number | PF6300000 | ||
| UN number | 1061 | ||
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InChI
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SMILES
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| Properties | |||
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Chemical formula
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CH5N | ||
| Molar mass | 31.06 g·mol−1 | ||
| Appearance | Colorless gas | ||
| Odor | Fishy, ammoniacal | ||
| Density | 656.2 kg m−3 (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 | ||
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Solubility in water
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1.08 kg L−1 (at 20 °C) | ||
| log P | −0.472 | ||
| Vapor pressure | 186.10 kPa (at 20 °C) | ||
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Henry's law
constant (kH) |
1.4 mmol Pa−1 kg−1 | ||
| Basicity (pKb) | 3.36 | ||
| Viscosity | 230 μPa s (at 0 °C) | ||
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Dipole moment
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1.31 D | ||
| Thermochemistry | |||
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Std enthalpy of
formation (ΔfH |
−23.5 kJ mol−1 | ||
| Hazards | |||
| Safety data sheet | emdchemicals.com | ||
| GHS pictograms | |||
| GHS signal word | DANGER | ||
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GHS hazard statements
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H220, H315, H318, H332, H335 | ||
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GHS precautionary statements
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P210, P261, P280, P305+351+338, P410+403 | ||
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EU classification (DSD)
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F+ Xn | ||
| R-phrases | R12, R20, R37/38, R41 | ||
| S-phrases | (S2), S16, S26, S39 | ||
| NFPA 704 |
4
3
0
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| Flash point | −10 °C; 14 °F; 263 K (liquid, gas is not flammable)[1] | ||
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Autoignition
temperature |
430 °C (806 °F; 703 K) | ||
| Explosive limits | 4.9–20.7% | ||
| Lethal dose or concentration (LD, LC): | |||
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LD50 (median dose)
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100 mg kg−1 (oral, rat) | ||
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LC50 (median concentration)
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1860 ppm (mouse, 2 hr)[1] | ||
| US health exposure limits (NIOSH): | |||
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PEL (Permissible)
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TWA 10 ppm (12 mg/m3)[1] | ||
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REL (Recommended)
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TWA 10 ppm (12 mg/m3)[1] | ||
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IDLH (Immediate danger)
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100 ppm[1] | ||
| Related compounds | |||
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Related alkanamines
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ethylamine, dimethylamine, trimethylamine | ||
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Related compounds
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ammonia | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) | |||
| Infobox references | |||
Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one H atom replaced by a methyl group. It is the simplest primary amine. It is sold as a solution in methanol, ethanol, THF, and 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 fish. Methylamine is used as a building block for the synthesis of many other commercially available compounds.
Contents
- 1 Industrial production
- 2 Laboratory methods
- 3 Reactivity and applications
- 4 Biological chemistry
- 5 Safety
- 6 See also
- 7 References
Industrial production
Methylamine is prepared commercially by the reaction of ammonia with methanol in the presence of a silicoaluminate catalyst. Dimethylamine and trimethylamine are coproduced; the reaction kinetics and reactant ratios determine the ratio of the three products. The product most favoured by the reaction kinetics is trimethylamine.[2]
- CH3OH + NH3 → CH3NH2 + H2O
In this way, an estimated 115,000 tons were produced in 2005.[3]
Laboratory methods
Methylamine was first prepared in 1849 by Wurtz by the hydrolysis of methyl isocyanate and related compounds.[3][4] An example of this process includes the use of Hofmann rearrangement to yield methylamine from acetamide and bromine gas.[5][6]
In the laboratory methylamine hydrochloride is readily prepared by various other methods. One method entails treating formaldehyde with ammonium chloride.[7]
- NH4Cl + H2CO → [CH2=NH2]Cl + H2O
- [CH2=NH2]Cl + H2CO + H2O → [CH3NH3]Cl + HCOOH
The colorless hydrochloride salt can be converted to the amine by the addition of strong base, like NaOH:
- [CH3NH3]Cl + NaOH → CH3NH2 + NaCl + H2O
Another method entails reducing nitromethane with zinc and hydrochloric acid.[8]
Reactivity and applications
Methylamine is a good nucleophile as it is highly basic and unhindered, although, 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 for liquid ammonia.[9]
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.[3]
Biological chemistry
Methylamine arises as a result of putrefaction and is a substrate for methanogenesis.[10]
Additionally, methylamine is produced during PADI4-dependent arginine demethylation.[11]
Safety
The LD50 (mouse, s.c.) is 2.5 g/kg.[12]
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.[13]
Methylamine is also controlled as a List 1 precursor chemical by the United States Drug Enforcement Administration due to its use in the production of methamphetamine.
See also
- Methylammonium halide
References
- ^ a b c d e "NIOSH Pocket Guide to Chemical Hazards #0398". National Institute for Occupational Safety and Health (NIOSH).
- ^ Corbin D.R.; Schwarz S.; Sonnichsen G.C. (1997). "Methylamines synthesis: A review". Catalysis Today 37 (24): 71–102. doi:10.1016/S0920-5861(97)00003-5. CS1 maint: Multiple names: authors list (link)
- ^ a b c Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
- ^ Charles-Adolphe Wurtz (1849) "Sur une série d'alcalis organiques homologues avec l'ammoniaque" (On a series of homologous organic alkalis containing ammonia), Comptes rendus … , 28 : 223-226. Note: Wurtz's empirical formula for methylamine is incorrect because chemists in that era used an incorrect atomic mass for carbon (6 instead of 12).
- ^ Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry, 4th Ed. London: Longman. p. 128. ISBN 9780582444072.
- ^ Cohen, Julius (1900). Practical Organic Chemistry 2nd Ed. London: Macmillan and Co., Limited. p. 72.
- ^ Marvel, C. S.; Jenkins, R. L. (1941). "Methylamine Hydrochloride". Org. Synth. CS1 maint: Multiple names: authors list (link); Coll. Vol. 1, p. 347
- ^ Gatterman, Ludwig; and Wieland, Heinrich (1937). Laboratory Methods of Organic Chemistry. Edinburgh, UK: R & R Clark, Limited. p. 157-158. CS1 maint: Multiple names: authors list (link)
- ^ M. G. DeBacker, El B. Mkadmi, F. X. Sauvage, J.-P. Lelieur, M. J. Wagner, R. Concepcion. J. Kim, L. E. H. McMills, J. L. Dye "The Lithium−Sodium−Methylamine System: Does a Low-Melting Sodide Become a Liquid Metal?" J. Am. Chem. Soc., 1996, vol. 118, pp 1997–2003. doi:10.1021/ja952634p
- ^ Thauer, R. K., "Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson", Microbiology, 1998, 144, 2377-2406.
- ^ Ng, SS; Yue, WW; Oppermann, U; Klose, RJ (February 2009). "Dynamic protein methylation in chromatin biology.". Cellular and molecular life sciences : CMLS 66 (3): 407–22. doi:10.1007/s00018-008-8303-z. PMID 18923809.
|access-date=requires|url=(help) - ^ The Merck Index, 10th Ed. (1983), p.864, Rahway: Merck & Co.
- ^ CDC - NIOSH Pocket Guide to Chemical Hazards
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Japanese Journal
- 高エネルギー物質研究会 平成26年度研究成果報告書
- 宇宙航空研究開発機構研究開発報告 JAXA-RR-14-005, 1-10, 2015-03
- NAID 110009893597
- Kinetics and Mechanisms of Supercritical Water Oxidation of Methylamines
- Journal of chemical engineering of Japan 39(9), 971-979, 2006-09-01
- NAID 10018244071
- Application of a New Selective Noncatalytic NO Reduction System to Diesel Exhaust(<Special Issue>Recent Combustion Technology in Internal Combustion Engines)
- JSME international journal. Ser. B, Fluids and thermal engineering 46(1), 131-136, 2003-02-15
- NAID 110003479138
Related Links
- Mitsubishi Gas Chemical ,MGC,Products,Monomethylamine,m-MA ... ここから本文になります。
- Aminomethane, Methylamine (anhydrous), Methylamine (aqueous), Monomethylamine CAS No. 74-89-5 RTECS No. PF6300000 DOT ID & Guide 1061 118(anhydrous) 1235 132(aqueous) Formula CH 3 NH 2 Conversion 1 ppm = 1 ...
Related Pictures
★リンクテーブル★
| リンク元 | 「モノメチルアミン」「aminomethane」「methylamine」 |
「モノメチルアミン」
「aminomethane」