3-Nitro-5-(trifluoromethyl)benzaldehyde: FAQs & Lab Guide

3-Nitro-5-(trifluoromethyl)benzaldehyde is a highly electron-deficient aromatic aldehyde bearing both a nitro and a trifluoromethyl substituent on the benzene ring, making it a versatile electrophilic building block widely used in pharmaceutical and materials chemistry research.

CAS-style Functional Groups

Aldehyde (–CHO), Nitro (–NO₂), Trifluoromethyl (–CF₃)

Electronic Character

Strongly electron-deficient aromatic ring due to meta-NO₂ and meta-CF₃ substituents

Recommended Storage

Store in a cool, dry, well-ventilated area, away from heat and incompatible materials; keep container tightly sealed

Primary Synthetic Use

Electrophilic building block for condensation reactions (imines, Knoevenagel, reductive amination) and pharmaceutical intermediate synthesis

SKU

N733475

Molecular Formula

C₈H₄F₃NO₃

What Is 3-Nitro-5-(trifluoromethyl)benzaldehyde?

3-Nitro-5-(trifluoromethyl)benzaldehyde is an aromatic aldehyde in which the benzene ring carries a nitro group (–NO₂) at the 3-position and a trifluoromethyl group (–CF₃) at the 5-position, with the aldehyde function (–CHO) at the 1-position. Both substituents are strongly electron-withdrawing, making the aldehyde carbon exceptionally electrophilic and the ring highly activated toward nucleophilic aromatic substitution under appropriate conditions.

The combination of the –CF₃ and –NO₂ groups confers high lipophilicity and metabolic stability to derivatives, properties that are particularly prized in medicinal chemistry and agrochemical research. The compound is a solid at room temperature and is typically handled as a powder or crystalline material.

Handling, Safety, and Storage

As with all nitro-substituted aromatic compounds, appropriate personal protective equipment (PPE) — including gloves, safety goggles, and a laboratory coat — should be worn when handling 3-Nitro-5-(trifluoromethyl)benzaldehyde. Work should be conducted in a well-ventilated fume hood to minimize inhalation of dust or vapors.

The compound should be stored in a tightly sealed container in a cool, dry location away from direct sunlight, sources of ignition, and incompatible materials such as strong oxidizers, strong bases, and reducing agents. Avoid contact with skin, eyes, and mucous membranes. In case of skin or eye contact, flush immediately with copious water and seek medical attention. Always consult the Safety Data Sheet (SDS) provided with the product before use.

Waste disposal must comply with local environmental regulations governing halogenated and nitro-aromatic compounds.

Solubility and Common Solvents

3-Nitro-5-(trifluoromethyl)benzaldehyde is generally soluble in common polar aprotic solvents such as dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), and acetonitrile, as well as in chlorinated solvents such as dichloromethane and chloroform. Solubility in water is expected to be low due to the strongly hydrophobic –CF₃ group.

For stock solution preparation, DMSO is often the solvent of choice in biological screening applications, while dichloromethane or ethyl acetate is preferred for organic synthesis workups. Researchers should verify solubility empirically for their specific concentration and temperature requirements, as solubility data specific to this compound were not provided in the source material.

Synthetic Applications and Reactivity

The aldehyde group in 3-Nitro-5-(trifluoromethyl)benzaldehyde participates readily in a wide range of classical carbonyl reactions. Key transformations include:

• Imine (Schiff base) formation: Condensation with primary amines to yield imines, useful as ligands or pharmaceutical intermediates.
• Knoevenagel condensation: Reaction with active methylene compounds to generate α,β-unsaturated derivatives for further functionalization.
• Reductive amination: Conversion to substituted benzylamines using reducing agents such as sodium cyanoborohydride or sodium triacetoxyborohydride.
• Wittig and HWE reactions: Olefination to produce stilbene-type or vinyl-type fluorinated intermediates.
• Nucleophilic addition: Reaction with organometallic reagents (Grignard, organolithium) to afford secondary alcohols.

The electron-withdrawing substituents accelerate reactions at the aldehyde center, making this compound a highly reactive electrophile compared with unsubstituted benzaldehyde.

Ordering and Product Specifications

3-Nitro-5-(trifluoromethyl)benzaldehyde is available from Aladdin Scientific under SKU N733475. When placing an order, researchers should confirm the available pack sizes, purity grade, and current pricing through the Aladdin product page or by contacting customer service.

For bulk or custom quantities, institutional pricing, or questions about purity certificates (CoA) and analytical data, please reach out to Aladdin's sales team directly. Expedited shipping options may be available depending on your location and local regulations governing the transport of aromatic nitro compounds.

Always reference the SKU N733475 when communicating with customer support to ensure accurate order fulfillment and avoid confusion with structurally similar analogs.

Frequently asked questions

What is the molecular formula and key structural features of 3-Nitro-5-(trifluoromethyl)benzaldehyde?

The molecular formula is C₈H₄F₃NO₃. The compound features a benzene ring substituted with an aldehyde (–CHO) at position 1, a nitro group (–NO₂) at position 3, and a trifluoromethyl group (–CF₃) at position 5. Both –NO₂ and –CF₃ are strongly electron-withdrawing, making the carbonyl highly electrophilic.

In which solvents is 3-Nitro-5-(trifluoromethyl)benzaldehyde most soluble?

The compound is generally soluble in polar aprotic solvents such as DMSO, DMF, and acetonitrile, as well as in chlorinated solvents like dichloromethane and chloroform. Aqueous solubility is expected to be low due to the hydrophobic trifluoromethyl group. Researchers should verify solubility empirically for their specific experimental conditions.

What types of chemical reactions can 3-Nitro-5-(trifluoromethyl)benzaldehyde undergo?

This compound readily undergoes carbonyl-based reactions including imine (Schiff base) formation with primary amines, Knoevenagel condensation with active methylene compounds, reductive amination, Wittig and Horner-Wadsworth-Emmons (HWE) olefination, and nucleophilic addition with organometallic reagents. The electron-withdrawing substituents enhance reactivity at the aldehyde center.

How should 3-Nitro-5-(trifluoromethyl)benzaldehyde be stored to maintain stability?

Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, away from direct sunlight, heat sources, and incompatible materials such as strong oxidizers and strong bases. Following these precautions helps prevent decomposition and maintains reagent quality over time.

What is the Aladdin SKU for 3-Nitro-5-(trifluoromethyl)benzaldehyde, and how can I request a Certificate of Analysis?

The Aladdin SKU is N733475. To request a Certificate of Analysis (CoA) or analytical data, contact Aladdin Scientific's customer service team and provide the SKU and your lot number. CoA documents confirm purity and key physical data for your records and regulatory requirements.

References

1. Aladdin Scientific product listing: 3-Nitro-5-(trifluoromethyl)benzaldehyde, SKU N733475.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for carbonyl reactions of aromatic aldehydes.)
3. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Fluorine in medicinal chemistry. Chemical Society Reviews, 2008. (General reference for CF₃ group properties in medicinal chemistry.)

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