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Revision as of 20:46, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII', 'ChEBI').← Previous edit		Latest revision as of 22:46, 21 October 2024 edit undo2601:280:4d81:220:6088:347b:f207:1345 (talk) I added missing information on the legal status of the compound in the summary. I provided the legal code 21 CFR § 1310.02, but not the reference: https://www.ecfr.gov/current/title-21/chapter-II/part-1310/section-1310.02Tags: Visual edit Mobile edit Mobile web edit
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	{{chembox		{{Chembox
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 408562079		| verifiedrevid = 443744511
	| Reference=<ref>'']'', 12th Edition, '''3808'''.</ref>		| Reference = <ref>'']'', 12th Edition, '''3808'''.</ref>
			| ImageFile1 = EtNH2.svg
	| ImageFileL1 = Ethylamine-2D-skeletal.png
	| ImageNameL1 = Simplified skeletal formula		| ImageNameL1 = Skeletal formula of ethylamine
			| ImageFileL2 = Ethylamine-3D-balls.png
	| ImageSizeR1 = 140px
			| ImageFileL2_Ref = {{chemboximage|correct|??}}
	| ImageFileR1 = Ethylamine-2D-flat.png
			| ImageNameL2 = Ball and stick model of ethylamine
	| ImageSizeR1 = 120px
			| ImageFileR2 = Ethylamine-3D-vdW.png
	| ImageNameR1 = Full structural formula
			| ImageFileR2_Ref = {{chemboximage|correct|??}}
	| ImageFile2 = Ethylamine-3D-balls.png
			| ImageNameR2 = Spacefill model of ethylamine
	| ImageSize2 = 180px
			| PIN = Ethanamine
	| ImageName2 = Ball-and-stick model
			| OtherNames = Ethylamine
	| IUPACName = Ethanamine
			|Section1={{Chembox Identifiers
	| OtherNames = Monoethylamine, Aminoethane, 1-Aminoethane, Ethamine
			| CASNo = 75-04-7
	| Section1 = {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| PubChem = 6341
	| ChemSpiderID = 6101		| ChemSpiderID = 6101
	| KEGG_Ref = {{keggcite|correct|kegg}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| UNII = YG6MGA6AT5
			| UNII_Ref = {{fdacite|correct|FDA}}
			| EINECS = 200-834-7
			| UNNumber = 1036
	| KEGG = C00797		| KEGG = C00797
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| InChIKey = QUSNBJAOOMFDIB-UHFFFAOYAL
			| MeSHName = ethylamine
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| ChEBI = 15862
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 14449		| ChEMBL = 14449
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| RTECS = KH2100000
			| Beilstein = 505933
			| Gmelin = 897
			| 3DMet = B00176
			| SMILES = CCN
	| StdInChI = 1S/C2H7N/c1-2-3/h2-3H2,1H3		| StdInChI = 1S/C2H7N/c1-2-3/h2-3H2,1H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = QUSNBJAOOMFDIB-UHFFFAOYSA-N		| StdInChIKey = QUSNBJAOOMFDIB-UHFFFAOYSA-N
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| CASNo = 75-04-7
	| CASNo_Ref = {{cascite|correct|CAS}}
	| EINECS = 200-834-7
	| PubChem = 6341
	| UNII = YG6MGA6AT5
	| ChEBI = 15862
	| SMILES = NCC
	| InChI = 1/C2H7N/c1-2-3/h2-3H2,1H3
	| RTECS = KH2100000
	}}
	| Section2 = {{Chembox Properties
	| Formula = C<sub>2</sub>H<sub>7</sub>N
	| MolarMass = 45.08 g/mol
	| Appearance = Light yellow liquid
	| Density = 0.689 g/cm<sup>3</sup>
	| MeltingPtC = -81
	| BoilingPtC = 16.6
	| Solubility = Miscible
	| VaporPressure = 121 kPa (20 °C)
	| Kb=4.3 x 10^-4<ref>Hall, H.K., ''J. Am. Chem. Soc.'', '''1957''', ''79'', 5441.</ref>
	}}
	| Section3 = {{Chembox Hazards
	| MainHazards = Harmful, corrosive, highly flammable
	| FlashPt = -17 °C
	| Autoignition = 385 °C
	| ExploLimits = 3.5-14%<sub>V</sub>
	| RPhrases = {{R12}}, {{R20}}, {{R22}}, {{R34}}, {{R36}}, {{R37}}, {{R38}}
	| SPhrases = {{S16}}, {{S26}}, {{S29}}
	| NFPA-H = 3
	| NFPA-F = 4
	| NFPA-R = 0
	| NFPA-O = ALK
	}}
	}}		}}
			|Section2={{Chembox Properties
			| C=2 | H=7 | N=1
	'''Ethylamine''' is an ] with the ] CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub>. This colourless gas has a strong ]-like odor. It is ] with virtually all solvents and is considered to be a weak ], as is typical for ]s. Ethylamine is widely used in chemical industry and ].
			| Appearance = Colourless gas
			| Odor = fishy, ammoniacal
			| Density = 688 kg m<sup>−3</sup> (at 15&nbsp;°C)
			| MeltingPtK = 188 to 194
			| BoilingPtK = 289 to 293
			| Solubility = Miscible
			| LogP = 0.037
			| VaporPressure = 116.5 kPa (at 20&nbsp;°C)
			| HenryConstant = 350 μmol Pa<sup>−1</sup> kg<sup>−1</sup>
			| pKa = 10.8 (for the ])
			| pKb = 3.2
			}}
			|Section3={{Chembox Thermochemistry
			| DeltaHf = −57.7 kJ mol<sup>−1</sup>
			}}
			|Section4={{Chembox Hazards
			| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
			| GHSSignalWord = '''DANGER'''
			| HPhrases = {{H-phrases|220|319|335}}
			| PPhrases = {{P-phrases|210|261|305+351+338|410+403}}
			| NFPA-H = 3
			| NFPA-F = 4
			| NFPA-R = 0
			| FlashPtC = −37
			| AutoignitionPtC = 383
			| ExploLimits = 3.5–14%
			| LD50 = {{Unbulleted list|265 mg kg<sup>−1</sup> <small>(dermal, rabbit)</small>|400 mg kg<sup>−1</sup> <small>(oral, rat)</small>}}
			| PEL = TWA 10 ppm (18 mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0263}}</ref>
			| REL = TWA 10 ppm (18 mg/m<sup>3</sup>)<ref name=NIOSH/>
			| IDLH = 600 ppm<ref name=NIOSH/>
			| LC50 = 1230 ppm (mammal)<ref name=IDLH>{{IDLH|75047|Ethylamine}}</ref>
			| LCLo = 3000 ppm (rat, 4 hr)<br/>4000 ppm (rat, 4 hr)<ref name=IDLH/>
			}}
			|Section5={{Chembox Related
			| OtherFunction_label = alkanamines
			| OtherFunction = {{Unbulleted list|]|]|]|]|]|]|]|]}}
			| OtherCompounds = {{Unbulleted list|]|]}}
			}}
			}}
			'''Ethylamine''', also known as '''ethanamine''', is an ] with the ] CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub>. This colourless gas has a strong ]-like odor. It condenses just below room temperature to a liquid ] with virtually all solvents. It is a nucleophilic ], as is typical for ]s. Ethylamine is widely used in chemical industry and ].<ref name=Ullmann/> It is a DEA list I chemical by 21 CFR § 1310.02.
	==Synthesis==		==Synthesis==
	Ethylamine is produced on a large scale by two processes. Most commonly ] and ] are combined in the presence of an oxide ]:		Ethylamine is produced on a large scale by two processes. Most commonly ] and ] are combined in the presence of an oxide ]:
	:CH<sub>3</sub>CH<sub>2</sub>OH + NH<sub>3</sub> → CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub> + H<sub>2</sub>O		:CH<sub>3</sub>CH<sub>2</sub>OH + NH<sub>3</sub> → CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub> + H<sub>2</sub>O
	In this reaction, ethylamine is coproduced together with ] and ]. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially.<ref>Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke, “Amines, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.{{DOI|10.1002/14356007.a02_001}}</ref>		In this reaction, ethylamine is coproduced together with ] and ]. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially.<ref name=Ullmann>Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke, "Amines, Aliphatic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.{{doi|10.1002/14356007.a02_001}}</ref>
	It is also produced by ] of ].		It is also produced by ] of ].
	:CH<sub>3</sub>CHO + NH<sub>3</sub> + H<sub>2</sub> → CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub> + H<sub>2</sub>O		:CH<sub>3</sub>CHO + NH<sub>3</sub> + H<sub>2</sub> → CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub> + H<sub>2</sub>O
	Ethylamine can be prepared by several other routes, but these are not economical. ] and ] combine to give ethylamine in the presence of an ] or related basic ]s.<ref>Ulrich Steinbrenner, Frank Funke, Ralf Böhling, , United States Patent 7161039.</ref>		Ethylamine can be prepared by several other routes, but these are not economical. ] and ] combine to give ethylamine in the presence of a ] or related basic ]s.<ref>Ulrich Steinbrenner, Frank Funke, Ralf Böhling, {{webarchive|url=https://archive.today/20120912102105/http://www.patentstorm.us/patents/7161039-claims.html |date=2012-09-12 }}, United States Patent 7161039.</ref>
	:H<sub>2</sub>C=CH<sub>2</sub> + NH<sub>3</sub> → CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub>		:H<sub>2</sub>C=CH<sub>2</sub> + NH<sub>3</sub> → CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub>
	Hydrogenation of ], ], and ] affords ]. These reactions can be effected stoichiometrically using ]. In another route, ethylamine can be synthesized via ] of a haloethane (such as ] or ]) with ], utilizing a strong base such as ]. This method affords significant amounts of byproducts, including ] and ].<ref>, St Peter's School</ref>		Hydrogenation of ], ], and ] affords ethylamine. These reactions can be effected stoichiometrically using ]. In another route, ethylamine can be synthesized via ] of a haloethane (such as ] or ]) with ], utilizing a strong base such as ]. This method affords significant amounts of byproducts, including ] and ].<ref> {{webarchive|url=https://web.archive.org/web/20080528051626/http://intranet.st-peters.york.sch.uk/fileadmin/user_upload/chemistry/AS_Organic_Mechs/NS-Haloalkane-NH3.ppt |date=2008-05-28 }}, St Peter's School</ref>
	:CH<sub>3</sub>CH<sub>2</sub>Cl + NH<sub>3</sub> + KOH → CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub> + KCl + H<sub>2</sub>O		:CH<sub>3</sub>CH<sub>2</sub>Cl + NH<sub>3</sub> + KOH → CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub> + KCl + H<sub>2</sub>O
			Ethylamine is also produced naturally in the cosmos; it is a component of interstellar gases.<ref>NRAO, "Discoveries Suggest Icy Cosmic Start for Amino Acids and DNA Ingredients", Feb 28 2013</ref>
	==Reactions and applications==
	Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as ] and ]. Reaction with ] followed by oxidaton of the ] give diethyl], EtN=NEt.<ref>Ohme, R.; Preuschhof, H.; Heyne, H.-U. , ''Organic Syntheses'', Collected Volume 6, p.78 (1988)</ref> Ethylamine may be oxidized using a strong oxidizer such as ] to form ].
			==Reactions==
			Like other simple ] amines, ethylamine is a ]: the pK<sub>a</sub> of <sup>+</sup> has been determined to be 10.8<ref>''Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 9th Ed.'' (1991), (J. N. Delgado and W. A. Remers, Eds.) p.878, Philadelphia: Lippincott and 10.63.</ref><ref>{{cite journal|author=H. K. Hall, Jr.|year=1957|journal=J. Am. Chem. Soc.|volume=79|pages=5441–5444|title=Correlation of the Base Strengths of Amines|issue=20|doi=10.1021/ja01577a030}}</ref>
			Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as ] and ]. Reaction with ] followed by oxidation of the ] give diethyl], EtN=NEt.<ref>{{Cite journal |date=1972 |title=AZOETHANE |url=http://orgsyn.org/demo.aspx?prep=CV6P0078 |journal=Organic Syntheses |volume=52 |pages=11 |doi=10.15227/orgsyn.052.0011}}</ref> Ethylamine may be oxidized using a strong oxidizer such as ] to form ].
			Ethylamine like some other small primary amines is a good solvent for ] metal, giving the ] <sup>+</sup> and the ]. Such solutions are used for the ] of unsaturated ], such as ]s<ref>Kaiser, E. M.; Benkeser R. A. {{webarchive|url=https://web.archive.org/web/20070930224411/http://www.orgsyn.org/orgsyn/pdfs/CV6P0852.pdf |date=2007-09-30 }}, ''Organic Syntheses'', Collected Volume 6, p.852 (1988)</ref> and ].
			==Applications==
	Ethylamine like some other small primary amines is a good solvent for ] metal, giving the ] <sup>+</sup> and the ]. Evaporation of these solutions, gives back lithium metal. Such solutions are used for the ] of unsaturated ], such as ]s<ref>Kaiser, E. M.; Benkeser R. A. , ''Organic Syntheses'', Collected Volume 6, p.852 (1988)</ref> and ].
			Ethylamine is a precursor to many herbicides including ] and ]. It is found in rubber products as well.<ref name=Ullmann/>
			Ethylamine is used as a precursor chemical along with ] (as opposed to ] and ] in ketamine synthesis) in the ] synthesis of cyclidine ] ] 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 agent ] and the ] ] and have been detected on the black market, being marketed for use as a recreational ] and ]. This produces a cyclidine with the same mechanism of action as ketamine (]) but with a much greater potency at the PCP binding site, a longer half-life, and significantly more prominent ] effects.<ref>{{Cite web|title= World Health Organization Critical Review Report of Ketamine, 34th ECDD 2006/4.3|url=https://www.who.int/medicines/areas/quality_safety/4.3KetamineCritReview.pdf}}</ref>
	Ethylamine is a precursor to many herbicides including ] and ]. It is found in rubber products as well.
	==References==		==References==
			{{Reflist}}
	<references/>
	==External links==		==External links==
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