 | |||
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Ethanamine | |||
| Other names Ethylamine | |||
| Identifiers | |||
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3D model (JSmol) | |||
| 505933 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.000.759 | ||
| EC Number |
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| 897 | |||
| KEGG |
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| MeSH | ethylamine | ||
| RTECS number |
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| UNII | |||
| UN number | 1036 | ||
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| Properties | |||
| C2H7N | |||
| Molar mass | 45.085 g·mol−1 | ||
| Appearance | Colourless gas | ||
| Odor | fishy, ammoniacal | ||
| Density | 688 kg m−3 (at 15 °C) | ||
| Melting point | −85 to −79 °C; −121 to −110 °F; 188 to 194 K | ||
| Boiling point | 16 to 20 °C; 61 to 68 °F; 289 to 293 K | ||
| Miscible | |||
| logP | 0.037 | ||
| Vapor pressure | 116.5 kPa (at 20 °C) | ||
Henry's law constant (kH) | 350 μmol Pa−1 kg−1 | ||
| Acidity (pKa) | 10.8 (for theConjugate acid) | ||
| Basicity (pKb) | 3.2 | ||
| Thermochemistry | |||
Std enthalpy of formation(ΔfH⦵298) | −57.7 kJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
  | |||
| Danger | |||
| H220,H319,H335 | |||
| P210,P261,P305+P351+P338,P410+P403 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | −37 °C (−35 °F; 236 K) | ||
| 383 °C (721 °F; 656 K) | |||
| Explosive limits | 3.5–14% | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
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LC50 (median concentration) | 1230 ppm (mammal)[3] | ||
LCLo (lowest published) | 3000 ppm (rat, 4 hr) 4000 ppm (rat, 4 hr)[3] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 10 ppm (18 mg/m3)[2] | ||
REL (Recommended) | TWA 10 ppm (18 mg/m3)[2] | ||
IDLH (Immediate danger) | 600 ppm[2] | ||
| Related compounds | |||
Related alkanamines | |||
Related compounds | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Ethylamine, also known asethanamine, is anorganic compound with theformula CH3CH2NH2. This colourless gas has a strongammonia-like odor. It condenses just below room temperature to a liquidmiscible with virtually all solvents. It is a nucleophilicbase, as is typical foramines. Ethylamine is widely used in chemical industry andorganic synthesis.[4] It is a DEA list I chemical by 21 CFR § 1310.02.
Ethylamine is produced on a large scale by two processes. Most commonlyethanol andammonia are combined in the presence of an oxidecatalyst:
In this reaction, ethylamine is coproduced together withdiethylamine andtriethylamine. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially.[4]It is also produced byreductive amination ofacetaldehyde.
Ethylamine can be prepared by several other routes, but these are not economical.Ethylene andammonia combine to give ethylamine in the presence of asodium amide or related basiccatalysts.[5]
Hydrogenation ofacetonitrile,acetamide, andnitroethane affords ethylamine. These reactions can be effected stoichiometrically usinglithium aluminium hydride. In another route, ethylamine can be synthesized vianucleophilic substitution of a haloethane (such aschloroethane orbromoethane) withammonia, utilizing a strong base such aspotassium hydroxide. This method affords significant amounts of byproducts, includingdiethylamine andtriethylamine.[6]
Ethylamine is also produced naturally in the cosmos; it is a component of interstellar gases.[7]
Like other simplealiphatic amines, ethylamine is aweak base: the pKa of [CH3CH2NH3]+ has been determined to be 10.8[8][9]
Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such asacylation andprotonation. Reaction withsulfuryl chloride followed by oxidation of thesulfonamide give diethyldiazene, EtN=NEt.[10] Ethylamine may be oxidized using a strong oxidizer such aspotassium permanganate to formacetaldehyde.
Ethylamine like some other small primary amines is a good solvent forlithium metal, giving theion [Li(amine)4]+ and thesolvated electron. Such solutions are used for thereduction of unsaturatedorganic compounds, such asnaphthalenes[11] andalkynes.
Ethylamine is a precursor to many herbicides includingatrazine andsimazine. It is found in rubber products as well.[4]
Ethylamine is used as a precursor chemical along withbenzonitrile (as opposed too-chlorobenzonitrile andmethylamine in ketamine synthesis) in theclandestine synthesis of cyclidinedissociativeanesthetic agents (the analogue of ketamine which is missing the 2-chloro group on the phenyl ring, and its N-ethyl analog) which are closely related to the well known anesthetic agentketamine and therecreational drugphencyclidine and have been detected on the black market, being marketed for use as a recreationalhallucinogen andtranquilizer. This produces a cyclidine with the same mechanism of action as ketamine (NMDA receptor antagonism) but with a much greater potency at the PCP binding site, a longer half-life, and significantly more prominentparasympathomimetic effects.[12]
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