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			{{Short description|Hydrocarbon compound (HC≡C–CH3)}}
			{{distinguish|propane|propene}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 267269156		| verifiedrevid = 406858995
⚫	| Name = '''Methylacetylene'''
			| Name = Propyne
	| ImageFile = propyne.png
			| ImageFile = PROPYNE.png
	| ImageSize = 120px
			| ImageSize = 120px
	| ImageName = Methylacetylene
		⚫	| ImageName = Methylacetylene
	| ImageFile1 = Propyne3D.png
			| ImageFile1 = Propyne-3D-vdW.png
	| ImageSize1 = 180px
			| ImageSize1 = 180px
	| IUPACName = Propyne
			| PIN = Propyne<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013 (Blue Book) | chapter = Characteristic (Functional) and Substituent Groups | publisher = ] | date = 2014 | location = Cambridge | page = 374 | doi = 10.1039/9781849733069-00372 | isbn = 978-0-85404-182-4}}</ref><ref group="note">"Prop-1-yne" mistake fixed in the {{Webarchive|url=https://web.archive.org/web/20190801093648/https://www.qmul.ac.uk/sbcs/iupac/bibliog/BBerrors.html |date=2019-08-01 }}. The locant is omitted according to P-14.3.4.2&nbsp;(d), p.&nbsp;31 for propene and P-31.1.1.1, Examples, p.&nbsp;374 for propyne.</ref>
⚫	| OtherNames = Methylacetylene<br />Methyl acetylene
			| SystematicName =
⚫	| Section1 = {{Chembox Identifiers
		⚫	| OtherNames = Methylacetylene<br />Methyl acetylene<br />Allylene
⚫	| CASNo = 74-99-7
	| CASNo_Ref = {{cascite}}		| IUPACName =
		⚫	| Section1 = {{Chembox Identifiers
⚫	| SMILES = CC#C
		⚫	| CASNo = 74-99-7
			| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 086L40ET1B
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 116902
		⚫	| SMILES = CC#C
			| EINECS = 200-828-4
			| PubChem = 6335
			| ChemSpiderID = 6095
			| InChI = 1/C3H4/c1-3-2/h1H,2H3
			| InChIKey = MWWATHDPGQKSAR-UHFFFAOYAI
			| StdInChI = 1S/C3H4/c1-3-2/h1H,2H3
			| StdInChIKey = MWWATHDPGQKSAR-UHFFFAOYSA-N
			| RTECS =
			| MeSHName = C022030
			| ChEBI = 48086
			| ChEBI_Ref = {{ebicite|correct|ebi}}
			| Beilstein = 878138
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula = C<sub>3</sub>H<sub>4</sub>		| Formula = {{chem2|C3H4}}
	| MolarMass = 40.0639 g/mol		| MolarMass = 40.0639 g/mol
	| Density = 0.53 g/cm³		| Density = 0.53 g/cm<sup>3</sup>
	| MeltingPtC = -102.7		| MeltingPtC = -102.7
	| BoilingPtC = -23.2		| BoilingPtC = -23.2
			| Appearance = Colorless gas<ref name=NIOSH/>
			| Odor = Sweet<ref name=NIOSH/>
			| VaporPressure = 5.2 atm (20°C)<ref name=NIOSH/>
	}}		}}
			| Section3 = {{Chembox Hazards
			| PEL = TWA 1000 ppm (1650 mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0392}}</ref>
			| ExploLimits = 1.7%-?<ref name=NIOSH/>
			| IDLH = 1700 ppm<ref name=NIOSH/>
			| REL = TWA 1000 ppm (1650 mg/m<sup>3</sup>)<ref name=NIOSH/>
			}}
			| Section4 =
			| Section5 =
			| Section6 =
	}}		}}
	'''Methylacetylene''' ('''propyne''') is an ] with the ] {{carbon}}]<sub>3</sub>C≡CH. It is a component of ] along with its ] ] (allene), which is commonly used in ]. Unlike ], methylacetylene can be safely condensed.<ref name=Ullmann>Peter Pässler, Werner Hefner, Klaus Buckl, Helmut Meinass, Andreas Meiswinkel, Hans-Jũrgen Wernicke, Günter Ebersberg, Richard Müller, Jürgen Bässler, Hartmut Behringer, Dieter Mayer, "Acetylene" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2007. 10.1002/14356007.a01 097.pub2</ref>		'''Propyne''' ('''methylacetylene''') is an ] with the ] {{chem2|CH3C\tCH}}. It is a component of ]—along with its ] ] (allene), which was commonly used in ]. Unlike ], propyne can be safely ].<ref name=Ullmann>Peter Pässler, Werner Hefner, Klaus Buckl, Helmut Meinass, Andreas Meiswinkel, Hans-Jürgen Wernicke, Günter Ebersberg, Richard Müller, Jürgen Bässler, Hartmut Behringer, Dieter Mayer, "Acetylene" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim 2007 ({{doi|10.1002/14356007.a01_097.pub2}}).</ref>
	==Production and equilibrium with allene==		==Production and equilibrium with propadiene==
	Methylacetylene exists in equilibrium with ], the mixture of methylacetylene and ] being called MAPD:		Propyne exists in equilibrium with ], the mixture of propyne and propadiene being called MAPD:
			:<chem>H3CC#CH <=> H2C=C=CH2</chem>
	:H<sub>3</sub>CC&equiv;CH {{unicode|⇌}} H<sub>2</sub>C=C=CH<sub>2</sub>
	K<sub>eq</sub> = 0.22 (270 °C), 0.1 K (5 °C)		The coefficient of equilibrium ''K''<sub>eq</sub> is 0.22 at 270&nbsp;°C or 0.1 at 5&nbsp;°C.
	MAPD is produced as a side product, often an undesirable one, by ] ] to produce ], an important ] in the ].<ref name=Ullmann/> MAPD interferes with the ] ] of propene.		MAPD is produced as a side product, often an undesirable one, by ] ] to produce ], an important ] in the ].<ref name=Ullmann/> MAPD interferes with the ] ] of propene.
			===Laboratory methods===
			Propyne can also be synthesized on laboratory scale by reducing ],<ref>{{cite journal|author1=Keiser, Edward |author2=Breed, Mary |name-list-style=amp |title=The Action of Magnesium Upon the Vapors of the Alcohols and a New Method of Preparing Allylene|journal=Journal of the Franklin Institute|year=1895|volume=CXXXIX|issue=4 |pages=304–309|url=https://books.google.com/books?id=jn-VkwcIt5QC&q=allylene+franklin+magnesium&pg=PA309|access-date=20 February 2014|doi=10.1016/0016-0032(85)90206-6}}</ref> ] or ]<ref>{{cite journal|last=Reiser, Edward II.|title=The preparation of Allylene, and the Action of Magnesium upon Organic Compounds|journal=The Chemical News and Journal of Industrial Science|year=1896|volume=LXXIV|pages=78–80|url=https://books.google.com/books?id=TxgAAAAAMAAJ&q=allylene+magnesium+preparing&pg=PA78|access-date=20 February 2014}}</ref> vapors over magnesium.
	==Use as a rocket fuel==		==Use as a rocket fuel==
	Research by European space concerns into using light ] with ] as a relatively high performing ] combination which would also be less toxic than the commonly used MMH/NTO (]/]) systems, showed that propyne would be highly advantageous as a ] for craft intended for ]al operations. This conclusion was reached based upon a ] expected to reach 370 ] if oxygen is used as oxidizer, a high ] and ], and the moderate ], which causes the chemical to present fewer problems in storage than for example a ] that needs to be kept at extremely low temperatures. (See ].)		European space companies have researched using light ] with ], a relatively high performing ] combination that would also be less toxic than the commonly used MMH/NTO (]/]). Their research showed{{citation needed|date=September 2013}} that propyne would be highly advantageous as a ] for craft intended for ]al operations. They reached this conclusion based upon a ] expected to reach 370 ] with oxygen as the oxidizer, a high ] and ]—and the moderate ], which makes the chemical easier to store than ]s that must be kept at extremely low temperatures.<ref>{{Cite web |last=Valentian |first=Dominique |last2=Sippel |first2=Martin |last3=Grönland |first3=Tor-Arne |last4=Baker |first4=Adam |last5=van Den Meulen |first5=Jaap |last6=Fratacci |first6=Georges |last7=Caramelli |first7=Fabio |date=2004 |title=Green propellants options for launchers, manned capsules and interplanetary missions |url=http://www.la.dlr.de/ra/sart/publications/pdf/esa02-2004.pdf |url-status=dead |archive-url=https://web.archive.org/web/20060110171612/http://www.la.dlr.de/ra/sart/publications/pdf/esa02-2004.pdf |archive-date=2006-01-10 |website=la.dlr.de |publisher=] Lampoldshausen}}</ref>
	==Organic chemistry==		==Organic chemistry==
	Propyne is a convenient three-carbon building block for ]. Deprotonation with ] gives ]. This ] reagent adds to ] groups, producing ]s and ]s.<ref>{{OrgSynth | author = Michael J. Taschner, Terry Rosen, and Clayton H. Heathcock | title = Ethyl Isocrotonate | collvol = 7 | collvolpages = 226| year = 1990 | prep = CV7P0226}}</ref> Whereas purified propyne is expensive, MAPP gas can be used to cheaply generate large amounts of the reagent. <ref>{{US patent reference | number = 5744071 | y = 1996 | m = 11 | d = 19 | inventor = Philip Franklin Sims, Anne Pautard-Cooper | title = Processes for preparing alkynyl ketones and precursors thereof }}</ref>		Propyne is a convenient three-carbon building block for ]. Deprotonation with ] gives ]. This ] reagent adds to ] groups, producing ]s and ]s.<ref>{{OrgSynth | author1 = Michael J. Taschner|author2=Terry Rosen|author3=Clayton H. Heathcock | title = Ethyl Isocrotonate | collvol = 7 | collvolpages = 226| year = 1990 | prep = CV7P0226}}</ref> Whereas purified propyne is expensive, MAPP gas could be used to cheaply generate large amounts of the reagent.<ref>{{US patent reference | number = 5744071 | y = 1996 | m = 11 | d = 19 | inventor = Philip Franklin Sims, Anne Pautard-Cooper | title = Processes for preparing alkynyl ketones and precursors thereof }}</ref>
			Propyne, along with ], is also used to synthesize ] ]s in the ] of ].<ref name=Cyclization>{{cite journal|author1=Reppe, Walter |author2=Kutepow, N |author3=Magin, A |name-list-style=amp |title=Cyclization of Acetylenic Compounds|journal=Angewandte Chemie International Edition in English|year=1969|volume=8|issue=10|pages=727–733|doi=10.1002/anie.196907271}}</ref>
⚫	==External links==
⚫	*
			The chemical shift of an alkynyl proton and propargylic proton generally occur in the same region of the ] spectrum. In propyne, these two signals have almost exactly the same chemical shifts, leading to overlap of the signals, and the <sup>1</sup>H NMR spectrum of propyne, when recorded in deuteriochloroform on a 300&nbsp;MHz instrument, consists of a single signal, a sharp singlet resonating at 1.8 ppm.<ref>{{Cite book|title=Organic chemistry|first1=Marc|last1=Loudon|first2=Jim|last2=Parise|others=Parise, Jim, 1978-|isbn=9781936221349|edition= Sixth|location=Greenwood Village, Colorado|publisher=W. H. Freeman|oclc=907161629|date = 2015-08-26}}</ref>
			==Notes==
			<references group="note" />
	==References==		==References==
	<references/>		<references/>
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		⚫	==External links==
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	{{Alkynes}}		{{Alkynes}}
			{{Molecules detected in outer space}}
			{{Hydrides by group}}
			{{Authority control}}
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