3-(3-Cyanophenyl)acrylic Acid: Properties & Lab Use FAQ

3-(3-Cyanophenyl)acrylic acid is a bifunctional cinnamic acid derivative bearing both a meta-positioned nitrile group and an α,β-unsaturated carboxylic acid moiety, making it a versatile building block for pharmaceutical, materials, and synthetic chemistry research.

Chemical Name

3-(3-Cyanophenyl)acrylic acid

Common Synonym

(E)-3-(3-cyanophenyl)acrylic acid; meta-cyanocinnamate acid

SKU / Product Code

C191400

Functional Groups

Nitrile (–CN), α,β-unsaturated carboxylic acid (–CH=CH–COOH)

Molecular Formula

C₁₀H₇NO₂

Molecular Weight

173.17 g/mol

Typical Physical State

Solid (powder or crystalline) at room temperature

What Is 3-(3-Cyanophenyl)acrylic Acid?

3-(3-Cyanophenyl)acrylic acid is an aromatic acrylic acid derivative in which a cyano (–CN) group is located at the meta position of the phenyl ring. It belongs to the broader class of cinnamic acid analogues, which are α,β-unsaturated arylacrylic acids widely used in organic synthesis.

The molecule contains two distinct reactive handles: the electrophilic β-carbon of the acrylate system (susceptible to Michael addition and cycloaddition reactions) and the nitrile group, which can be hydrolysed to an amide or carboxylic acid, reduced to an amine, or used directly in heterocycle-forming reactions. This dual reactivity is the primary reason the compound is valued as a synthetic intermediate.

The preferred stereoisomer in research use is the thermodynamically stable trans (E)-configuration, consistent with most naturally occurring cinnamic acid derivatives.

Key Chemical Properties and Handling

Solubility: 3-(3-Cyanophenyl)acrylic acid is sparingly soluble in water under neutral conditions but dissolves more readily in polar organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), ethanol, and acetone. Solubility in aqueous buffers can be enhanced by mild basification (pH >8), which deprotonates the carboxylic acid (estimated pKa ~4–5, consistent with other cinnamic acid derivatives).

Stability: The compound is stable under normal laboratory storage conditions when kept dry and away from strong oxidising agents, strong bases, and prolonged UV exposure. The α,β-unsaturated acid system may undergo slow photo-isomerisation under intense light.

Handling precautions: Standard laboratory PPE (gloves, safety glasses, lab coat) should be worn. Work in a well-ventilated area or fume hood. The nitrile group is not considered acutely toxic in the same manner as cyanide salts; however, appropriate caution and adherence to your institution's chemical safety protocols are required. Always consult the product Safety Data Sheet (SDS) supplied with C191400 before use.

Research and Synthetic Applications

3-(3-Cyanophenyl)acrylic acid is primarily employed as a bifunctional building block in medicinal and synthetic organic chemistry. Representative applications include:

• Pharmaceutical intermediates: The compound serves as a precursor for the synthesis of heterocyclic scaffolds (e.g., isoquinolinones, pyrazoles, and indazoles) via cyclisation of the nitrile or conjugate addition to the alkene.
• Polymer and material science: Cinnamic acid derivatives are known photocrosslinkable monomers; introduction of a nitrile group modifies electronic properties and can influence photoreactivity and Tg of resulting polymers.
• Biological activity screening: Cinnamic acid analogues have been reported in the literature as scaffolds for anti-inflammatory, antimicrobial, and anticancer lead compounds. The meta-cyano substitution alters electronic density and lipophilicity relative to unsubstituted cinnamic acid, enabling structure–activity relationship (SAR) studies.
• Click and coupling chemistry: The carboxylic acid can be activated for amide bond formation (e.g., via EDC/NHS or HATU coupling), and the nitrile can participate in tetrazole-forming [3+2] cycloadditions.

These broad applications make C191400 useful across drug discovery, materials research, and methodology development laboratories.

Storage and Shelf Life Recommendations

To maintain compound integrity, observe the following storage guidelines for 3-(3-Cyanophenyl)acrylic acid (C191400):

• Temperature: Store at room temperature (15–25 °C) in a cool, dry location unless otherwise specified on the product label or Certificate of Analysis (CoA).
• Container: Keep tightly sealed in the original container to prevent moisture uptake and contamination.
• Light: Store away from direct light sources to minimise potential photoisomerisation of the acrylic acid double bond.
• Atmosphere: No special inert-atmosphere requirement is indicated for typical laboratory use, but long-term storage under argon or nitrogen can extend stability.
• Shelf life: Specific shelf life data should be confirmed on the CoA accompanying each lot of C191400. In general, solid cinnamic acid derivatives stored as described above remain stable for at least 2 years when unopened.

If discolouration or physical changes are observed, re-characterise the material by HPLC or NMR before use in critical experiments.

Ordering, Purity, and Quality Assurance

Product availability: 3-(3-Cyanophenyl)acrylic acid is available from Aladdin Scientific under SKU C191400. Please visit the product page or contact our sales team for current pack sizes, pricing, and lead times.

Purity: Aladdin Scientific supplies research-grade reagents with purity specifications confirmed by analytical methods such as HPLC and NMR. The exact purity specification for C191400 is stated on the product page and the accompanying Certificate of Analysis (CoA). Customers requiring higher purity for specialised applications (e.g., reference standards, GMP-adjacent work) should contact technical support to discuss options.

Quality documentation: A CoA, including lot-specific analytical data, is available for download on the product page or upon request. Safety Data Sheets (SDS) are also available and must be reviewed before handling.

Custom quantities: For bulk or custom quantities not listed on the standard product page, please contact Aladdin Scientific's sales team directly.

Frequently asked questions

What is the molecular formula and molecular weight of 3-(3-Cyanophenyl)acrylic acid?

3-(3-Cyanophenyl)acrylic acid has the molecular formula C₁₀H₇NO₂ and a molecular weight of 173.17 g/mol. It contains a phenyl ring substituted at the meta position with a cyano group, connected via a trans-alkene to a carboxylic acid terminus.

Which solvents are recommended for dissolving 3-(3-Cyanophenyl)acrylic acid?

The compound dissolves well in polar aprotic solvents such as DMSO and DMF, as well as in protic solvents like ethanol and acetone. Aqueous solubility is limited at neutral pH but improves significantly under basic conditions (pH >8) due to deprotonation of the carboxylic acid group. Water alone is generally not a suitable solvent for this compound at neutral pH.

What are the main synthetic uses of 3-(3-Cyanophenyl)acrylic acid in research?

This compound is used as a bifunctional building block in medicinal chemistry, materials science, and synthetic methodology. Key applications include the preparation of heterocyclic scaffolds via nitrile cyclisation, amide coupling through the carboxylic acid moiety, Michael addition reactions at the β-carbon, and structure–activity relationship studies in biological screening programmes targeting anti-inflammatory or anticancer activity.

How should 3-(3-Cyanophenyl)acrylic acid be stored to ensure long-term stability?

Store the compound at room temperature (15–25 °C) in a tightly sealed container, away from light, moisture, and strong oxidants or bases. Long-term stability can be further improved by storing under an inert atmosphere (nitrogen or argon). Always refer to the lot-specific CoA for confirmed shelf-life data.

Is a Certificate of Analysis (CoA) or Safety Data Sheet (SDS) available for C191400?

Yes. Both the Certificate of Analysis and Safety Data Sheet for C191400 are available from Aladdin Scientific. The CoA contains lot-specific purity and analytical data, while the SDS provides essential safety, handling, and disposal information. These documents can be downloaded from the product page or requested from our customer service team.

Can 3-(3-Cyanophenyl)acrylic acid undergo photoisomerisation?

Yes, like other cinnamic acid derivatives, the α,β-unsaturated double bond in 3-(3-Cyanophenyl)acrylic acid is susceptible to photoisomerisation (E→Z) upon prolonged exposure to UV or intense visible light. To minimise this risk, store and handle the compound away from direct light sources and use amber glassware where possible.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for cinnamic acid reactivity and α,β-unsaturated carbonyl chemistry.)
2. Sova, M. Antioxidant and antimicrobial activities of cinnamic acid derivatives. Mini Rev. Med. Chem. 2012, 12, 749–767. (Background on biological activity of cinnamic acid analogues.)
3. Aladdin Scientific. Product Page: 3-(3-Cyanophenyl)acrylic acid, SKU C191400. (Source of product identity, SKU, and availability information.)

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