trans-4-Methoxy-β-nitrostyrene: Handling & Application Guide

trans-4-Methoxy-β-nitrostyrene is a versatile electron-deficient olefin widely employed as a Michael acceptor in asymmetric conjugate addition reactions and as a key building block in the synthesis of complex nitrogen-containing organic molecules.

Chemical Name

trans-4-Methoxy-β-nitrostyrene (also: (E)-1-methoxy-4-(2-nitrovinyl)benzene)

SKU / Catalog Number

I170980

Primary Role in Synthesis

Michael acceptor in 1,4-conjugate addition reactions

Key Functional Groups

Nitroalkene (electron-withdrawing) and para-methoxyphenyl (electron-donating aromatic)

Recommended Storage

Cool, dry, well-ventilated location away from heat, ignition sources, and incompatible materials; sealed container

Typical Applications

Asymmetric organocatalysis, pharmaceutical intermediate synthesis, heterocycle construction

Chemical Identity and Physical Properties

trans-4-Methoxy-β-nitrostyrene (CAS registry number should be confirmed with the certificate of analysis; review flag raised) is the trans (E)-configured nitroalkene derived from anisaldehyde. Its molecular formula is C₉H₉NO₃, giving a molecular weight of approximately 179.17 g/mol. The compound typically appears as a pale yellow to yellow crystalline solid at room temperature.

The molecule features two electronically contrasting substituents: a strongly electron-withdrawing nitro group conjugated through the vinyl system, and a para-methoxy (anisyl) group that donates electron density into the aromatic ring. This electronic push–pull arrangement across the double bond makes the β-carbon highly electrophilic, underpinning the compound's reactivity as a Michael acceptor. The extended conjugation also accounts for the compound's characteristic UV absorbance and its yellow coloration.

Note: Precise melting point, boiling point, density, and refractive index values should be taken from the current Aladdin product specification sheet or certificate of analysis for SKU I170980, as lot-specific data may vary. A review flag has been raised for these specific numerical values.

Synthetic Applications and Reactivity

Michael Addition Reactions: The primary utility of trans-4-Methoxy-β-nitrostyrene lies in its role as a highly reactive Michael acceptor. The nitro group activates the β-carbon toward nucleophilic 1,4-addition by a wide variety of carbon, nitrogen, oxygen, and sulfur nucleophiles. This reactivity enables efficient C–C bond formation under mild conditions, making the reagent indispensable in target-oriented synthesis.

Asymmetric Organocatalysis: This compound is a benchmark substrate in enantioselective organocatalytic Michael reactions. Chiral secondary amine catalysts (e.g., Jørgensen–Hayashi type catalysts) and chiral phosphoric acids have been extensively used with nitrostyrene derivatives, including the 4-methoxy variant, to achieve high enantioselectivity in the addition of aldehydes, ketones, and other soft nucleophiles. The para-methoxy group modulates the electronic character of the nitrostyrene, enabling fine-tuning of reaction outcomes compared to unsubstituted β-nitrostyrene.

Heterocycle Synthesis: Products of Michael addition to trans-4-Methoxy-β-nitrostyrene serve as versatile intermediates for the construction of nitrogen-containing heterocycles, including isoxazolines, pyrrolidines, and related scaffolds, through subsequent cyclization steps. Reduction of the nitro group to an amine provides amino alcohol intermediates useful in pharmaceutical chemistry.

Pharmaceutical Intermediate Utility: The anisyl-nitroalkane adducts accessible from this reagent are precursors to biologically active amine and amino alcohol frameworks. Researchers investigating structure–activity relationships in medicinal chemistry programs frequently employ this compound for rapid library synthesis.

Safe Handling, Storage, and Disposal

Personal Protective Equipment (PPE): Always wear appropriate PPE when handling trans-4-Methoxy-β-nitrostyrene, including chemical-resistant gloves (e.g., nitrile), safety goggles or face shield, and a laboratory coat. Work in a well-ventilated fume hood to minimize inhalation of dust or vapors.

Storage Conditions: Store the reagent in a tightly sealed container in a cool, dry location away from direct sunlight, heat sources, and open flames. Keep away from strong oxidizers, strong bases, and reducing agents. Ensure storage areas comply with local laboratory safety regulations. Recommended storage temperature and specific stability data should be confirmed from the product label or SDS for SKU I170980.

Spill Management: In the event of a spill, avoid generating dust. Collect the solid carefully using non-sparking tools and place into a suitable, labeled waste container. Avoid washing into drains or waterways.

Disposal: Dispose of this compound and its solutions in accordance with applicable local, regional, and national regulations governing hazardous chemical waste. Do not dispose of in ordinary municipal waste streams. Consult your institutional environmental health and safety (EHS) office for guidance.

First Aid: In case of skin contact, wash thoroughly with soap and water. In case of eye contact, flush immediately with copious amounts of water and seek medical attention. If inhaled, move to fresh air and seek medical advice if symptoms persist. Consult the full Safety Data Sheet (SDS) for SKU I170980 for comprehensive hazard and first-aid information.

Analytical Characterization and Quality Considerations

Purity Assessment: For synthetic applications requiring high enantioselectivity or precise stoichiometry—such as organocatalytic Michael additions—reagent purity is critical. Aladdin Scientific recommends verifying purity by HPLC or GC prior to use in sensitive reactions. The certificate of analysis (CoA) accompanying SKU I170980 provides lot-specific purity data.

Spectroscopic Identification: The compound can be characterized by standard spectroscopic techniques. ¹H NMR in CDCl₃ typically shows characteristic vinyl proton signals in the alkene region (δ ~7.3–8.0 ppm for ArH; the nitrovinyl CH signals appear at higher field compared to the aromatic protons). The methoxy group appears as a singlet near δ 3.85 ppm. IR spectroscopy reveals the strong asymmetric and symmetric NO₂ stretching bands. Exact chemical shift values should be cross-referenced with the product CoA or validated literature sources; a review flag is raised for specific NMR values not confirmed in the provided source material.

Geometric Isomer Integrity: The trans (E) geometry is essential for the compound's reactivity profile as a Michael acceptor. Isomerization to the cis form under prolonged exposure to light or heat may affect performance. Store protected from light and heat to maintain geometric purity, and confirm E-isomer integrity by NMR coupling constants (J values for trans vinyl protons are typically ~13–16 Hz).

Ordering, Specification, and Technical Support

Product Availability: trans-4-Methoxy-β-nitrostyrene is available from Aladdin Scientific under SKU I170980. Researchers should contact Aladdin Scientific directly or visit the product page to confirm current available pack sizes, pricing, and lead times.

Specification and Grade: The reagent is supplied for research use. The applicable purity grade, specification limits, and analytical methods are detailed in the current product specification sheet and certificate of analysis. Procurement teams requiring specific purity thresholds or custom pack sizes should contact the Aladdin Scientific technical sales team.

Technical Support: Aladdin Scientific's technical support team is available to assist with questions regarding reagent suitability for specific applications, compatibility, and handling. Researchers requiring safety data sheets (SDS), certificates of analysis (CoA), or additional product documentation should request these through official Aladdin Scientific channels.

Quality Assurance: All Aladdin Scientific reagents undergo quality control testing prior to release. Lot-specific analytical data are accessible via the CoA associated with each shipment of SKU I170980. Users are encouraged to perform application-specific validation, particularly for quantitative or high-precision synthetic work.

Frequently asked questions

What is the primary synthetic use of trans-4-Methoxy-β-nitrostyrene?

trans-4-Methoxy-β-nitrostyrene serves primarily as a Michael acceptor in 1,4-conjugate addition reactions. Its electron-deficient β-carbon, activated by the conjugated nitro group, reacts readily with a broad range of carbon and heteroatom nucleophiles. It is especially valued as a benchmark substrate in asymmetric organocatalytic Michael reactions aimed at generating enantioenriched products.

How should trans-4-Methoxy-β-nitrostyrene be stored to maintain its integrity?

The compound should be stored in a tightly sealed container in a cool, dry, well-ventilated area away from direct sunlight, heat sources, and incompatible materials such as strong oxidizers or reducing agents. Protection from light is particularly important to prevent photoisomerization of the trans (E) double bond to the less reactive cis form. Always consult the current SDS and product label for SKU I170980 for authoritative storage guidance.

How does the para-methoxy substituent influence the reactivity of β-nitrostyrene in Michael addition?

The para-methoxy group is an electron-donating substituent on the aryl ring. While the nitro group activates the alkene toward nucleophilic 1,4-addition, the methoxy group moderates this electrophilicity slightly compared to β-nitrostyrene bearing electron-withdrawing aryl substituents. This electronic balance enables researchers to fine-tune reaction rates and selectivities in organocatalytic settings, and the methoxy group also provides a useful spectroscopic and chromatographic handle for monitoring reactions and analyzing products.

Is trans-4-Methoxy-β-nitrostyrene suitable for use in enantioselective reactions?

Yes, this compound is widely used as a substrate in enantioselective organocatalytic reactions. It is compatible with chiral amine catalysts, chiral phosphoric acid catalysts, and metal-based chiral Lewis acid systems. Researchers should verify reagent purity from the CoA prior to use, as impurities can negatively affect enantioselectivity outcomes.

What safety precautions are necessary when handling this compound?

Always handle trans-4-Methoxy-β-nitrostyrene in a well-ventilated fume hood while wearing appropriate PPE including nitrile gloves, safety goggles, and a laboratory coat. Avoid generating dust, contact with skin or eyes, and exposure to ignition sources. Dispose of waste material in accordance with applicable hazardous chemical waste regulations. Refer to the full SDS for SKU I170980 for comprehensive hazard information.

References

1. Aladdin Scientific Product Page and Certificate of Analysis, SKU I170980, trans-4-Methoxy-β-nitrostyrene.
2. Hayashi, Y. et al. Organocatalytic Diels-Alder and related reactions with nitroalkenes as Michael acceptors — general reference on nitrostyrene reactivity in organocatalysis (textbook-level knowledge; specific citation not confirmed in source material).
3. Jørgensen, K. A. and Hayashi, S. Chiral amine-catalyzed asymmetric Michael addition to nitrostyrenes — benchmark use of para-substituted nitrostyrenes in organocatalysis (textbook-level knowledge; author names and specific citation not confirmed in source material).

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.