Ethylamines

Ethylamine

Names
Preferred IUPAC name Ethanamine
Other names Ethylamine
Identifiers
CAS Number	75-04-7 Y
3D model (JSmol)	Interactive image
3DMet	B00176
Beilstein Reference	505933
ChEBI	CHEBI:15862 Y
ChemSpider	6101 Y
ECHA InfoCard	100.000.759
EC Number	200-834-7
Gmelin Reference	897
KEGG	C00797 Y
MeSH	ethylamine
PubChem CID	6341
RTECS number	KH2100000
UNII	YG6MGA6AT5 Y
UN number	1036
InChI InChI=1S/C2H7N/c1-2-3/h2-3H2,1H3 Y Key: QUSNBJAOOMFDIB-UHFFFAOYSA-N Y
SMILES CCN
Properties
Chemical formula	C2H7N
Molar mass	45.09 g·mol−1
Appearance	Colourless gas
Odor	fishy, ammoniacal
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
Solubility in water	Miscible
log P	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 the Conjugate acid)
Basicity (pKb)	3.2
Thermochemistry
Std enthalpy of formation (ΔfHo298)	−57.7 kJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H220, H319, H335
GHS precautionary statements	P210, P261, P305+351+338, P410+403
NFPA 704	4 3 0
Flash point	−37 °C (−35 °F; 236 K)
Autoignition temperature	383 °C (721 °F; 656 K)
Explosive limits	3.5–14%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	265 mg kg−1(dermal, rabbit) 400 mg kg−1(oral, rat)
LC50 (median concentration)	1230 ppm (mammal)
LCLo (lowest published)	3000 ppm (rat, 4 hr) 4000 ppm (rat, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 10 ppm (18 mg/m3)
REL (Recommended)	TWA 10 ppm (18 mg/m3)
IDLH (Immediate danger)	600 ppm
Related compounds
Related alkanamines	Methylamine Ethylenediamine Propylamine Isopropylamine 1,2-Diaminopropane 1,3-Diaminopropane Isobutylamine tert-Butylamine
Related compounds	Monomethylhydrazine 2-Methyl-2-nitrosopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Ethylamine is an organic compound with the formula CH₃CH₂NH₂. This colourless gas has a strong ammonia-like odor. It is miscible with virtually all solvents and is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

pK_a (of conjugate acid CH₃CH₂NH₃) = 10.8

Ethylamine is produced on a large scale by two processes. Most commonly ethanol and ammonia are combined in the presence of an oxide catalyst:

In this reaction, ethylamine is coproduced together with diethylamine and triethylamine. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially. It is also produced by reductive amination of acetaldehyde.

Ethylamine can be prepared by several other routes, but these are not economical. Ethylene and ammonia combine to give ethylamine in the presence of a sodium amide or related basic catalysts.

Hydrogenation of acetonitrile, acetamide, and nitroethane affords ethylamine. These reactions can be effected stoichiometrically using lithium aluminium hydride. In another route, ethylamine can be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia, utilizing a strong base such as potassium hydroxide. This method affords significant amounts of byproducts, including diethylamine and triethylamine.