| Revision as of 12:10, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 400848855 of page Phenyl-2-nitropropene for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 15:17, 25 October 2024 edit BD2412 (talk | contribs)Autopatrolled, IP block exemptions, Administrators2,447,993 editsm clean up spacing around commas and other punctuation, replaced: ],, [, , → ,Tag: AWB |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| Reference = <ref name="Alfa" /><ref name="Sigma" /><ref name="Cayman" /><ref name="Biosynth" /><ref name="chemicalbook" /> |
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| verifiedrevid = 400847595 |
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| Verifiedfields = changed |
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| Name = 1-Phenyl-2-nitropropene |
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| ImageFile = Phenyl-2-nitropropene.svg |
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| verifiedrevid = 464200869 |
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| ImageName = right |
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| IUPACName = 1-Phenyl-2-nitropropene |
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| Name = 1-Phenyl-2-nitropropene |
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| ImageFile = |
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| OtherNames = P2NP, β-methyl-β-nitropropene, (2-Nitro-1-propenyl)benzene |
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{{multiple image |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| total_width = 290 |
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| image_style = border:1; |
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| image1 = Phenyl-2-nitropropene.svg |
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| image2 = P2NP_Crystals.png |
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| image3 = Phenyl-2-Nitropropene.png |
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| PIN = (2-Nitroprop-1-en-1-yl)benzene |
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| OtherNames = P2NP<br>1-Phenyl-2-nitropropene<br>β-methyl-β-nitropropene<br>trans-beta-Methyl-beta-Nitrostyrene<br>(2-Nitro-1-propenyl)benzene |
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| Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 1266396 |
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| ChemSpiderID = 1266396 |
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| PubChem = 1549520 |
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| PubChem = 1549520 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WGSVFWFSJDAYBM-BQYQJAHWSA-N |
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| StdInChIKey = WGSVFWFSJDAYBM-BQYQJAHWSA-N |
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| CASNo = <!-- blanked - oldvalue: 705-60-2 --> |
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| CASNo = 705-60-2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 18315-84-9 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1_Comment = (''E'') |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = YT17M2UOTY |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>9</sub>H<sub>9</sub>NO<sub>2</sub> |
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| Formula = C<sub>9</sub>H<sub>9</sub>NO<sub>2</sub> |
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| MolarMass = 163.17 g mol<sup>−1</sup> |
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| MolarMass = 163.17 g mol<sup>−1</sup> |
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| Appearance = solid |
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| Appearance = solid |
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| MeltingPt = 64-66 °C |
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| MeltingPtC = 64 to 66 |
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| Section7 = {{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| EUClass = Harmful ('''Xn''') |
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| GHSSignalWord = Warning |
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| RPhrases = {{R22}}, {{R36/37/38}} |
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| HPhrases = {{H-phrases|302|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|280|301+312|312|302+352|304+340|305+351+338|330|332+313|337+313|362+364}} |
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'''1-Phenyl-2-nitropropene''', or simply '''phenyl-2-nitropropene''', or '''P2NP''', as it is commonly referred to, is a ] from the ] group of compounds, with the formula C<sub>9</sub>H<sub>9</sub>NO<sub>2</sub>. It is a light-yellow crystalline solid with a distinct smell.<ref name="p2npim" /> Phenyl-2-nitropropene is used in the pharmaceutical industry to manufacture the drug ], an ] mixture used to treat ] and ]. P2NP and other similar nitrostyrenes are also employed in the ] of the amphetamine class, and are listed as drug precursors in many countries.<ref name="Erowid" /><ref name="Erowid2" /><ref name="Erowid3" /> |
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==Uses== |
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In the pharmaceutical industry, P2NP is used to produce a ] ] mixture, branded under the trade names ] and ], amongst others. In this case, the ] is ] and the ] is reduced,<ref name="ru1" /> thus 1-phenyl-2-nitropropene becomes 1-phenyl-2-aminopropane, which is another name for amphetamine. Different ] commonly ] (LAH), ], ] or ] are used in suitable ] like ] or ]. |
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] |
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The above diagram depicts P2NP reduction to amphetamine by either ], ], ], or ] used as ]. ], in the form of ], can also be used.<ref name="Erowid" /> |
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P2NP can also be reduced to ] (P2P), the precursor in the synthesis of ] by a few methods. One in which phenyl-2-nitropropene is reduced to phenyl-2-nitropropane using ], followed by ] of the nitro group with ] and ] to produce phenylacetone (1-phenyl-2-propan-2-one).<ref name="ErowidP2p" /> In another method, ] is the reducing agent and ] or ] are used as catalysts forming an intermediate which hydrolyzes into phenylacetone as well.<ref name="ErowidP2p" /> |
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==Synthesis== |
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In the lab, phenyl-2-nitropropene is produced by the reaction of ] and ] in the presence of a basic ] like ]. The reaction is a nitroaldol reaction, and is a variant of a ], which is one of a broader class of reactions called ], or simply Henry reactions. These are named after the German chemist ], and the Belgian chemist Louis Henry, respectively. |
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In this type of reaction, the basic catalyst deprotonates the nitroethane to form a ]. This anion nucleophilically adds to the ] forming a β-nitro alcohol, which is subsequently dehydrated to yield the ]. Water is produced as a byproduct, and must be actively removed from the reaction mixture. |
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Often, primary amines like ], ], and ] are used as catalysts, as is anhydrous ] at times.<ref name="p2npim" /> |
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Many other drugs of the amphetamine class are produced in a similar fashion, where substituted benzaldehyde derivatives are used to produce a different nitrostyrene, which is later reduced to the desired amine. One such reaction is the Knoevenagel condensation of ] with nitroethane, yielding 3,4-methylenedioxy-1-phenyl-2-nitropropene, or MDP2NP. This is reduced to ], or MDA, which can be methylated to ], or MDMA.<ref name="Erowid3" /> Another uses 2,5-dimethoxybenzaldehyde and nitromethane to yield 2,5-dimethoxy-β-nitrostyrene. |
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Many of these Knoevenagel condensations were used by ] to yield over 100 amphetamine derivatives, which he detailed in his book, '']''.<ref name="pihkal" /><ref name="p2npim" /><ref name="Erowid4" /> |
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==Safety and Storage== |
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P2NP is labeled as harmful by the ], and is a known irritant. Thus, breathing fumes and direct skin and eye contact should be avoided. |
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The ] for oral exposure in rats and mice is greater than 500 mg/kg and 1176 mg/kg, respectively. |
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Based on available data, the classification criteria are not met to classify P2NP as a ]. However, the toxicological properties have not been thoroughly investigated.<ref name=Cayman /><ref name=Biosynth /><ref name=Sigma /> |
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P2NP should be stored at 2 °C to 8 °C and away from strong ]s. At higher temperatures, P2NP is not very stable, and degrades with time.<ref name=Biosynth /><ref name="p2npim" /> |
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==References== |
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{{reflist|refs= |
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<!--Not available any more <ref name="AlfaOld"> {{webarchive|url=https://web.archive.org/web/20070927010259/http://www.alfa.com/MSDSPDF/English/A17831.pdf |date=2007-09-27 }}</ref> --> |
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<ref name="Alfa">, accessed on March 20, 2021</ref> |
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<ref name="chemicalbook">, accessed on March 21, 2021</ref> |
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<ref name=Cayman>Material Safety Data Sheet P2NP (PDF) from Cayman Chemical, accessed on March 20, 2021</ref> |
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<ref name=Biosynth>Material Safety Data Sheet 1-(Phenyl)2-nitropropene (PDF) from Biosynth Carbosynth, accessed on March 20, 2021</ref> |
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<ref name=Sigma>Material Safety Data Sheet trans-β-Methyl-β-nitrostyrene (PDF) from Sigma-Aldrich, accessed on March 20, 2021</ref> |
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<ref name="Erowid"></ref> |
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<ref name="Erowid2"></ref> |
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<ref name="Erowid3"></ref> |
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<ref name="Erowid4"></ref> |
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<ref name="ErowidP2p"></ref> |
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<ref name="pihkal">], Alexander Shulgin and Ann Shulgin, 1991</ref> |
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<ref name="p2npim">, 2021</ref> |
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<!--check those--> |
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<ref name="ru1">{{cite book| author = ] | chapter = Синтез амфетамина. Восстановительное аминирование (каталическое восстановление с использованием металла)| chapter-url = https://books.google.com/books?id=Nf2y_9j9i_kC&pg=PA12| format = | url = | title = Рекомендуемые методы обнаружения и анализа амфетамина, метамфетамина и их замещённых по циклу аналогов в конфискованных материалах | orig-year = | agency = | edition = |location= Нью-Йорк |date = 2007 |publisher= |volume= | pages = 12| series = | isbn = 9789214480303}}</ref> |
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<!--<ref name="ru2">{{cite book| author = ] | chapter = Синтез 1-фенил-2-пропанона| chapter-url = https://books.google.com/books?id=G_OfkRtfz8oC&pg=PA40| format = | url = | title = Бюллетень по наркотическим средствам | orig-year = | agency = | edition = |location= |date = 2008 |publisher= |volume= | pages = 40| series = | isbn = 978-92-1-448027-3}}</ref> --> |
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