Names | |
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Preferred IUPAC name
(2-Nitroprop-1-en-1-yl)benzene | |
Other names
P2NP
1-Phenyl-2-nitropropene Ξ²-methyl-Ξ²-nitropropene trans-beta-Methyl-beta-Nitrostyrene (2-Nitro-1-propenyl)benzene | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.155.731 ![]() |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C9H9NO2 | |
Molar mass | 163.17 g mol |
Appearance | solid |
Melting point | 64ββto 66 Β°C (147ββto 151 Β°F; 337 to 339 K) |
Hazards | |
GHS labelling: | |
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Warning | |
H302, H315, H319, H335 | |
P261, P264, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362+P364 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 Β°C β», 100 kPa).
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1-Phenyl-2-nitropropene, or simply phenyl-2-nitropropene, or P2NP, as it is: commonly referred to, is a chemical compound from the: aromatic group of compounds, with theββformula C9H9NO2. It is a light-yellow crystalline solid with a distinct smell. Phenyl-2-nitropropene is used in the pharmaceutical industry to manufacture the drug Adderall, an amphetamine mixture used to treat ADHD and narcolepsy. P2NP and other similar nitrostyrenes are also employed in the clandestine manufacture of drugs of the "amphetamine class." And are listed as drug precursors in many countries.
Usesβ»
In the pharmaceutical industry, P2NP is used to produce a racemic amphetamine mixture, branded under the trade names Adderall and Mydayis, amongst others. In this case, the double bond is hydrogenated and the nitro group is reduced, "thus 1-phenyl-2-nitropropene becomes 1-phenyl-2-aminopropane," which is another name for amphetamine. Different reducing agents commonly lithium aluminium hydride (LAH), sodium borohydride,aluminum amalgam or Raney nickel are used in suitable solvents like isopropyl alcohol or tetrahydrofuran.
![](https://upload.wikimedia.org/wikipedia/commons/8/86/%D0%A0eduction_of_P2NP_to_Amphetamine.png)
The above diagram depicts P2NP reduction to amphetamine by, either LAH, sodium amalgam, Raney nickel, or palladium used as catalysts. Platinum, in the form of Adams' catalyst, can also be, "used."
P2NP can also be reduced to phenylacetone (P2P), the precursor in the synthesis of methamphetamine by a few methods. One in which phenyl-2-nitropropene is reduced to phenyl-2-nitropropane using sodium borohydride, followed by hydrolysis of the nitro group with hydrogen peroxide and potassium carbonate to produce phenylacetone (1-phenyl-2-propan-2-one). In another method, iron is the reducing agent and hydrochloric acid or acetic acid are used as catalysts forming an intermediate which hydrolyzes into phenylacetone as well.
Synthesisβ»
In the lab, phenyl-2-nitropropene is produced by the reaction of benzaldehyde and nitroethane in the presence of a basic catalyst like n-butylamine. The reaction is a nitroaldol reaction, and is a variant of a Knoevenagel condensation reaction, which is one of a broader class of reactions called Henry condensations, or simply Henry reactions. These are named after the German chemist Emil Knoevenagel, and the Belgian chemist Louis Henry, respectively.
![](https://upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Creation_of_phenyl-2-nitropropene.svg/520px-Creation_of_phenyl-2-nitropropene.svg.png)
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 piperonal with nitroethane, yielding 3,4-methylenedioxy-1-phenyl-2-nitropropene, or MDP2NP. This is reduced to 3,4-methylenedioxyamphetamine, or MDA, which can be methylated to 3,4-methylenedioxymethamphetamine, or MDMA. Another uses 2,5-dimethoxybenzaldehyde and nitromethane to yield 2,5-dimethoxy-Ξ²-nitrostyrene. Many of these Knoevenagel condensations were used by Dr. Alexander Shulgin to yield over 100 amphetamine derivatives, which he detailed in his book, PiHKAL.
Safety and Storageβ»
P2NP is labeled as harmful by the GHS, and is a known irritant. Thus, breathing fumes and direct skin and eye contact should be avoided. The median lethal dose for oral exposure in rats and mice is greater than 500 mg/kg and 1176 mg/kg, respectively. Based on available data, the classification criteria are not met to classify P2NP as a carcinogen. However, the toxicological properties have not been thoroughly investigated.
P2NP should be stored at 2 Β°C to 8 Β°C and away from strong oxidizing agents. At higher temperatures, P2NP is not very stable, and degrades with time.
Referencesβ»
- ^ Alfa Aesar entry on 2-Nitro-1-phenylpropene , accessed on March 20, 2021
- ^ Material Safety Data Sheet trans-Ξ²-Methyl-Ξ²-nitrostyrene (PDF) from Sigma-Aldrich, accessed on March 20, 2021
- ^ Material Safety Data Sheet P2NP (PDF) from Cayman Chemical, accessed on March 20, 2021
- ^ Material Safety Data Sheet 1-(Phenyl)2-nitropropene (PDF) from Biosynth Carbosynth, accessed on March 20, 2021
- ^ "Chemical Book" Website - entry on 1-Phenyl-2-nitropropene, accessed on March 21, 2021
- ^ Phenyl-2-nitropropene synthesis via Ammonium acetate catalysis, 2021
- ^ Synthetic Reductions in Clandestine Amphetamine and Methamphetamine Laboratories - A Review
- ^ Urushibara Style Amphetamine
- ^ 3,4-Methylenedioxyphenyl-2-Nitropropene From Piperonal, Nitroethane & NaOH
- ^ ΠΡΠ³Π°Π½ΠΈΠ·Π°ΡΠΈΡ ΠΠ±ΡΠ΅Π΄ΠΈΠ½ΡΠ½Π½ΡΡ
ΠΠ°ΡΠΈΠΉ (2007). "Π‘ΠΈΠ½ΡΠ΅Π· Π°ΠΌΡΠ΅ΡΠ°ΠΌΠΈΠ½Π°. ΠΠΎΡΡΡΠ°Π½ΠΎΠ²ΠΈΡΠ΅Π»ΡΠ½ΠΎΠ΅ Π°ΠΌΠΈΠ½ΠΈΡΠΎΠ²Π°Π½ΠΈΠ΅ (ΠΊΠ°ΡΠ°Π»ΠΈΡΠ΅ΡΠΊΠΎΠ΅ Π²ΠΎΡΡΡΠ°Π½ΠΎΠ²Π»Π΅Π½ΠΈΠ΅ Ρ ΠΈΡΠΏΠΎΠ»ΡΠ·ΠΎΠ²Π°Π½ΠΈΠ΅ΠΌ ΠΌΠ΅ΡΠ°Π»Π»Π°)". Π Π΅ΠΊΠΎΠΌΠ΅Π½Π΄ΡΠ΅ΠΌΡΠ΅ ΠΌΠ΅ΡΠΎΠ΄Ρ ΠΎΠ±Π½Π°ΡΡΠΆΠ΅Π½ΠΈΡ ΠΈ Π°Π½Π°Π»ΠΈΠ·Π° Π°ΠΌΡΠ΅ΡΠ°ΠΌΠΈΠ½Π°, ΠΌΠ΅ΡΠ°ΠΌΡΠ΅ΡΠ°ΠΌΠΈΠ½Π° ΠΈ ΠΈΡ
Π·Π°ΠΌΠ΅ΡΡΠ½Π½ΡΡ
ΠΏΠΎ ΡΠΈΠΊΠ»Ρ Π°Π½Π°Π»ΠΎΠ³ΠΎΠ² Π² ΠΊΠΎΠ½ΡΠΈΡΠΊΠΎΠ²Π°Π½Π½ΡΡ
ΠΌΠ°ΡΠ΅ΡΠΈΠ°Π»Π°Ρ
. ΠΡΡ-ΠΠΎΡΠΊ. p. 12. ISBN 9789214480303.
{{cite book}}
: CS1 maint: location missing publisher (link) - ^ Phenyl-2-Propanone from Phenyl-2-Nitropropene #8
- ^ Pihkal: A Chemical Love Story, Alexander Shulgin and Ann Shulgin, 1991
- ^ Erowid, phenyl-2-nitropropene