Description

Phenyl-2-Nitropropene

Phenyl-2-nitropropene (P2NP) is a significant compound renowned for its diverse applications in organic chemistry, particularly in the synthesis of various substances. Lets delve into the composition, preparation, uses, synthesis methods, safety considerations, and best practices for P2NP storage, all curated to provide valuable insights for researchers and enthusiasts in the world of chemistry.

 

What Is Phenyl-2-Nitropropene (P2NP)?

Phenyl-2-nitropropene, also known by its chemical formula C9H10N2O2, is a nitroalkene with a phenyl group attached to the double bond of a 2-nitropropene structure. The compound is typically characterized by its pale yellow to light brown color in liquid form, with a strong olfactory presence.

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.

 

Composition of P2NP

The molecular structure of P2NP comprises:
– A phenyl group (C6H5)
– A nitro group (−NO2)
– An alkene structure (C=C) with propene as the parent compound.

The presence of both nitro and alkene functionalities endows P2NP with various reactivity patterns, making it a valuable scaffold in organic synthesis.

 

Phenyl-2-Nitropropene Properties

CAS Numbers: 705-60-2 | 18315-84-9
Chemical formula: C9H9NO2
Molar mass:  163.176 g·mol−1

Molecular Weight 163.17
Appearance: Yellow solid
Melting point:  64 to 66 °C (147 to 151 °F; 337 to 339 K)
ChemSpider: 1266396
ECHA InfoCard: 100.155.731
PubChem CID: 1549520
UNII: YT17M2UOTY
CompTox Dashboard (EPA): DTXSID601336391 , DTXSID1041188, DTXSID601336391

 

Preparation of P2NP

P2NP can be synthesized through several methods, with one of the most common routes involving a reaction between phenylacetone and nitromethane. This process typically employs a base such as sodium ethoxide to facilitate the reaction.

 

Step-by-Step Reaction Overview:

1. Start with Phenylacetone: As a precursor, phenylacetone is reacted with nitromethane.

2. Catalytic Base Addition: Sodium ethoxide is introduced as a catalytic base.

3. Formation of P2NP: The reaction leads to the formation of the nitroalkene, completing the synthesis of P2NP.

This method is popular for its simplicity and efficiency, allowing chemists to produce P2NP with relatively high yields.

 

Uses of P2NP

Phenyl-2-nitropropene’s unique properties make it particularly useful in various fields, including:

– Synthesis of Pharmaceuticals: P2NP is often a key intermediate in producing various pharmaceuticals, particularly those associated with the central nervous system.

– Research in Organic Chemistry: It serves as a critical building block for chemists exploring new compounds.

– Dyes and Pigments: P2NP is utilized in the synthesis of colorants due to its unique features.

Its versatility in applications underscores the significance of P2NP in both academic and industrial settings.

 

Reduction of P2NP to Amphetamine

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.

 

Safety Considerations

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.

When handling P2NP, safety is paramount due to the potential hazards associated with nitro compounds. Here are some critical safety measures:

– Use Personal Protective Equipment (PPE): Safety goggles, gloves, and lab coats should be worn to minimize skin and eye exposure.

– Work in a Well-Ventilated Area: Due to the possible release of harmful vapors, ensure that all reactions occur in a fume hood or well-ventilated space.

– Emergency Protocols: Have emergency showers and eyewash stations accessible, along with appropriate spill cleanup materials.

 

First Aid Measures

– Inhalation: Move to fresh air and seek medical attention if symptoms persist.

– Skin Contact: Wash with plenty of soap and water and seek medical attention if irritation occurs.

– Eye Contact: Rinse with water for several minutes and seek medical help immediately.

 

Storage of P2NP

Proper storage of P2NP is essential to maintain its integrity and prevent degradation. Here are some recommended practices:

– Refrigeration: Store P2NP in a cool environment at 2 °C to 8 °C and away from strong oxidizing agents, preferably in a refrigerator to slow any potential degradation reactions.

– Seal Container: Ensure that the container is tightly sealed to prevent moisture and air from affecting the compound.

– Label Clearly: Clearly label the container with the compound’s name, concentration, date of receipt, and hazard information.

– Avoid Light Exposure: Store in a dark place to protect the compound from light-induced degradation.

At higher temperatures, P2NP is not very stable, and degrades with time.

 

Conclusion

Phenyl-2-nitropropene (P2NP) plays a pivotal role in the dynamic field of organic chemistry, with its multifaceted applications ranging from pharmaceuticals to dyes. With a proper understanding of its composition, preparation methods, uses, and essential safety practices, chemists and researchers can effectively harness this compound in their respective fields.

Be sure to adhere to safety guidelines and best practices for storage to maximize the efficacy and safety of handling P2NP.