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Revision as of 14:27, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 462614815 of page Propadiene for the Chem/Drugbox validation project (updated: '').		Latest revision as of 20:32, 5 January 2025 edit Citation bot (talk | contribs)Bots5,429,312 edits Alter: date, title. Add: doi-access, authors 1-2. Removed URL that duplicated identifier. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Jay8g | #UCB_toolbar
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			{{Short description|1=Organic compound (H2C=C=CH2)}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{Chembox		{{Chembox
			| Verifiedimages = changed
⚫	| verifiedrevid = 406949009
			| Watchedfields = changed
⚫	| ImageFileL1 = Allene.png
		⚫	| verifiedrevid = 464215747
⚫	| ImageFileL1_Ref = {{chemboximage|correct|??}}
		⚫	| ImageFileL1 = Propadiene structure.svg
	| ImageSizeL1 = 121
		⚫	| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageNameL1 = Stereo structural formula of propadiene with explicit hydrogens		| ImageNameL1 = Stereo structural formula of propadiene with explicit hydrogens
	| ImageFileR1 = Allene3D.png		| ImageFileR1 = Allene3D.png
	| ImageFileR1_Ref = {{Chemboximage|correct|??}}		| ImageFileR1_Ref = {{Chemboximage|correct|??}}
		⚫	| ImageNameR1 = Spacefill model of propadiene
	| ImageSizeR1 = 121
⚫	| ImageNameR1 = Spacefill model of propadiene
	| ImageFile2 = Allene-CRC-IR-3D-balls.png		| ImageFile2 = Allene-CRC-IR-3D-balls.png
	| ImageFile2_Ref = {{Chemboximage|correct|??}}		| ImageFile2_Ref = {{Chemboximage|correct|??}}
	| ImageSize2 = 160		| ImageSize2 = 160
	| ImageName2 = Ball and stick model of propadiene		| ImageName2 = Ball and stick model of propadiene
			| PIN = Propadiene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 375 | doi = 10.1039/9781849733069 | isbn = 978-0-85404-182-4 | quote = The name allene, for {{chem2|CH2\dC\dCH2}}, is retained for general nomenclature only; substitution is allowed, but not by alkyl or any other group that extends the carbon chain, nor characteristic groups expressed by suffixes. The systematic name, propadiene, is the preferred IUPAC name. | last1 = Favre | first1 = Henri A. | last2 = Powell | first2 = Warren H. }}</ref>
	| IUPACName = Allene
			| OtherNames = Allene<ref name=iupac2013 /><br />Propadiene
	| SystematicName = <!-- Propa-1,2-diene (substitutive) OR dimethylenecarbon (additive) -->
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo = 463-49-0		| CASNo = 463-49-0
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
	| PubChem = 10037
			| UNII = 4AV0LZ8QKB
	| PubChem_Ref = {{Pubchemcite|correct|PubChem}}
	| ChemSpiderID = 9642		| PubChem = 10037
			| ChemSpiderID = 9642
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| EINECS = 207-335-3
	| UNNumber = 2200		| EINECS = 207-335-3
	| MeSHName = Propadiene		| UNNumber = 2200
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| MeSHName = Propadiene
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 37601		| ChEBI = 37601
	| ChEMBL = 116960		| ChEMBL = 116960
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| Beilstein = 1730774		| Beilstein = 1730774
	| Gmelin = 860		| Gmelin = 860
	| SMILES = C=C=C		| SMILES = C=C=C
		⚫	| StdInChI = 1S/C3H4/c1-3-2/h1-2H2
	| SMILES1 = C(=C)=C
		⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫	| StdInChI = 1S/C3H4/c1-3-2/h1-2H2
		⚫	| StdInChIKey = IYABWNGZIDDRAK-UHFFFAOYSA-N
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫	| StdInChIKey = IYABWNGZIDDRAK-UHFFFAOYSA-N
⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C = 3		| C=3 | H=4
		⚫	| Appearance = Colorless gas
⚫	| H = 4
			| MeltingPtC = -136
	| ExactMass = 40.031300128 g mol<sup>-1</sup>
		⚫	| BoilingPtC = -34
⚫	| Appearance = Colorless gas
	| MeltingPtC = -136		| LogP = 1.45}}
		⚫	|Section3={{Chembox Hazards
⚫	| BoilingPtC = -34
		⚫	| ExternalSDS =
	| LogP = 1.45}}
			| GHSPictograms = {{GHS flame}}<ref name="GESTIS">{{GESTIS|ZVG=13750 |CAS=463-49-0 |Name=Allene |Date=17 November 2020}}</ref>
⚫	| Section3 = {{Chembox Hazards
			| GHSSignalWord = Danger
⚫	| ExternalMSDS =
			| HPhrases = {{H-phrases|220}}<ref name=GESTIS/>
	| EUClass = {{Hazchem F+}}
			| PPhrases = {{P-phrases|210|377|381|410+403}}<ref name=GESTIS/>
	| RPhrases = {{R12}}
		⚫	| NFPA-H = 0
	| SPhrases = {{S9}}, {{S16}}, {{S33}}
	| NFPA-H = 0		| NFPA-F = 4
	| NFPA-F = 4		| NFPA-R = 3
	| NFPA-R = 3		| ExploLimits = 13%}}
	| ExploLimits = 13%}}
	}}		}}
			'''Propadiene''' ({{IPAc-en|p|r|oʊ|p|ə|ˈ|d|aɪ|iː|n}}) or '''allene''' ({{IPAc-en|ˈ|æ|l|iː|n}}) is the ] with the formula {{chem2|H2C\dC\dCH2}}. It is the simplest ], i.e. a compound with two adjacent carbon ]s.<ref>{{GoldBookRef | title = allenes | file = A00238}}</ref> As a constituent of ], it has been used as a fuel for specialized ].
			==Production and equilibrium with methylacetylene==
			Propadiene exists in equilibrium with ] (propyne) and the mixture is sometimes called MAPD for ''m''ethyl''a''cetylene-''p''ropa''d''iene:
			:{{chem2 | H3CC\tCH <-> H2C\dC\dCH2 }}
			for which {{nowrap|1=''K''{{sub|eq}} = 0.22}} at 270&nbsp;°C or 0.1 at 5&nbsp;°C.
			MAPD is produced as a side product, often an undesirable one, of ] of ] to produce ], an important ] in the ]. MAPD interferes with the ] ] of propene.<ref>Klaus Buckl, Andreas Meiswinkel "Propyne" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2008, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.m22_m01}}</ref>
			== Occurrence in Space ==
			In 2019 it was announced that propadiene had been detected in the atmosphere of Saturn's moon ] using the ].<ref>{{Cite journal |last1=Lombardo |first1=Nicholas A |last2=Nixon |first2=Conor A |last3=Greathouse |first3=Thomas K |last4=Bézard |first4=Bruno |last5=Jolly |first5=Antoine |last6=Vinatier |first6=Sandrine |last7=Teanby |first7=Nicholas A |last8=Richter |first8=Matthew J |last9=G Irwin |first9=Patrick J |last10=Coustenis |first10=Athena |last11=Flasar |first11=F Michael |date=2019-08-20 |title=Detection of Propadiene on Titan |journal=The Astrophysical Journal Letters |volume=881 |issue=2 |pages=L33 |doi=10.3847/2041-8213/ab3860 |doi-access=free |issn=2041-8205}}</ref> This was the first time that propadiene had been detected in space, and the second ] pair (paired with ]) detected in Titan's atmosphere, after ]-].<ref>{{Cite journal |last1=Moreno |first1=R. |last2=Lellouch |first2=E. |last3=Lara |first3=L. M. |last4=Courtin |first4=R. |last5=Bockelée-Morvan |first5=D. |last6=Hartogh |first6=P. |last7=Rengel |first7=M. |last8=Biver |first8=N. |last9=Banaszkiewicz |first9=M. |last10=González |first10=A. |date=December 2011 |title=First detection of hydrogen isocyanide (HNC) in Titan's atmosphere |url=http://www.aanda.org/10.1051/0004-6361/201118189 |journal=Astronomy & Astrophysics |volume=536 |pages=L12 |doi=10.1051/0004-6361/201118189 |issn=0004-6361}}</ref><ref>{{Cite journal |last1=Hébrard |first1=E. |last2=Dobrijevic |first2=M. |last3=Loison |first3=J. C. |last4=Bergeat |first4=A. |last5=Hickson |first5=K. M. |date=May 2012 |title=Neutral production of hydrogen isocyanide (HNC) and hydrogen cyanide (HCN) in Titan's upper atmosphere |url=http://www.aanda.org/10.1051/0004-6361/201218837 |journal=Astronomy & Astrophysics |volume=541 |pages=A21 |doi=10.1051/0004-6361/201218837 |issn=0004-6361}}</ref>
			==References==
			{{Reflist}}
			{{Hydrocarbons}}
			{{Authority control}}
			]
			]