4-Cyano-3-methylbenzoic acid: Properties, Uses & Lab Guide

4-Cyano-3-methylbenzoic acid is a bifunctional aromatic building block bearing both a carboxylic acid and a nitrile group on a methyl-substituted benzene ring, making it a versatile intermediate for pharmaceutical, agrochemical, and materials chemistry research.

CAS Number

To be confirmed — see product datasheet (C194823)

Molecular Formula

C9H7NO2

Molecular Weight

161.16 g/mol

Functional Groups

Carboxylic acid (–COOH) and nitrile (–CN) on a methylbenzene core

Appearance

Typically a white to off-white crystalline solid (verify with datasheet)

Storage Conditions

Store in a cool, dry, well-ventilated area away from incompatible materials; confirm exact conditions on SDS

Purity

Research-grade; confirm lot purity via Certificate of Analysis (CoA)

Chemical Identity and Physical Properties

4-Cyano-3-methylbenzoic acid (Aladdin SKU: C194823) is a substituted benzoic acid derivative in which the benzene ring carries a cyano (–CN) group at the 4-position and a methyl (–CH₃) group at the 3-position, in addition to the carboxylic acid (–COOH) at the 1-position. Its molecular formula is C₉H₇NO₂ and its molecular weight is 161.16 g/mol.

The simultaneous presence of two electron-withdrawing groups (–CN and –COOH) and one weak electron-donating group (–CH₃) on the aromatic ring creates a characteristic electronic environment that influences both the acidity of the carboxyl group and the reactivity of the nitrile toward nucleophilic addition or hydrolysis. Researchers should consult the product Certificate of Analysis (CoA) and Safety Data Sheet (SDS) supplied with SKU C194823 for confirmed physicochemical data including exact melting point, purity, and solubility.

Applications in Organic and Medicinal Chemistry

The dual functionality of 4-cyano-3-methylbenzoic acid makes it a valuable building block in multi-step synthetic sequences. The carboxylic acid moiety can participate in amide bond formation (via activation with coupling reagents such as EDC/HOBt or HATU), esterification, or decarboxylation reactions. The nitrile group is amenable to hydrolysis to the corresponding amide or carboxylic acid, reduction to a primary amine, cycloaddition to form tetrazole or oxazole heterocycles, and palladium-catalysed cross-coupling when converted to appropriate leaving-group derivatives.

In medicinal chemistry programs, compounds bearing the cyanobenzoic acid scaffold have been explored as precursors to pharmacophores including benzamide, isoindolinone, and phthalimide motifs. In materials science, nitrile-containing aromatic acids are used as ligands in metal-organic framework (MOF) construction. The methyl substituent at the 3-position introduces steric differentiation that can be exploited to direct regioselective reactions.

Note: Specific literature citations for these applications should be verified against primary literature before inclusion in publications.

Safe Handling, Storage, and Waste Disposal

Personal Protective Equipment (PPE): When handling 4-cyano-3-methylbenzoic acid, wear appropriate PPE including nitrile gloves, laboratory coat, and safety goggles. Work in a fume hood to avoid inhalation of dust or aerosols. The nitrile group is generally stable under ambient conditions but should not be exposed to strongly reducing agents or concentrated strong acids/bases without appropriate precautions.

Storage: Store the reagent in a tightly sealed container in a cool (typically 2–25 °C; confirm on SDS), dry, and well-ventilated location away from oxidisers, strong acids, and strong bases. Keep away from ignition sources if organic solvents are used in proximity.

Waste Disposal: Dispose of waste material in accordance with local, national, and institutional regulations for chemical waste. Do not pour down the drain. Consult the product SDS (available from Aladdin Scientific) for full hazard classification and disposal guidance.

Always consult the current SDS for SKU C194823 before first use, as hazard data supersedes general guidance.

Analytical Characterisation and Quality Verification

Researchers should verify the identity and purity of 4-cyano-3-methylbenzoic acid upon receipt using standard analytical techniques:

• HPLC: Reverse-phase HPLC with UV detection (typically monitored near 254 nm due to aromatic and nitrile chromophores) provides quantitative purity assessment. Compare retention time against a reference standard or published data.
• ¹H NMR: In DMSO-d₆ or CDCl₃, the spectrum should display aromatic protons (characteristic multiplets in the 7.5–8.5 ppm region), a singlet for the methyl group (~2.5 ppm), and a broad singlet for the carboxylic acid proton (~12–13 ppm).
• IR Spectroscopy: A strong nitrile stretch near 2230 cm⁻¹ and a carbonyl stretch of the carboxylic acid near 1680–1720 cm⁻¹ are expected signature absorptions.
• Mass Spectrometry: ESI-MS or APCI-MS should yield [M–H]⁻ at m/z 160.05 (negative ion mode) consistent with the molecular formula C₉H₇NO₂.

The Aladdin Certificate of Analysis (CoA) provides lot-specific analytical data; request the CoA for your batch at the time of ordering (SKU C194823).

Ordering, Procurement, and Availability

4-Cyano-3-methylbenzoic acid is available from Aladdin Scientific under SKU C194823. When placing an order, researchers and procurement staff should:

• Confirm the required quantity and pack size to minimise freeze-thaw cycles and ensure sufficient material for planned experimental campaigns.
• Request the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) at point of order to support regulatory compliance and in-house safety review.
• Check current pricing and stock availability on the Aladdin Scientific website or by contacting customer service, as availability and lead times may vary.
• Consider volume pricing for larger-scale synthetic programmes.

For technical questions regarding the reagent's suitability for a specific application, contact Aladdin Scientific's technical support team. All products are sold for research use only and are not intended for diagnostic, therapeutic, or food applications.

Frequently asked questions

What is 4-Cyano-3-methylbenzoic acid used for in research?

4-Cyano-3-methylbenzoic acid serves primarily as a bifunctional building block in organic synthesis. Its carboxylic acid group enables amide coupling, esterification, and related transformations, while the nitrile group can be hydrolysed, reduced, or incorporated into heterocyclic ring systems. It is particularly useful as an intermediate in medicinal chemistry and materials science programmes.

How should 4-Cyano-3-methylbenzoic acid be stored to ensure stability?

The compound should be stored in a tightly sealed container under cool, dry, and well-ventilated conditions, away from strong oxidisers, acids, and bases. Refer to the Safety Data Sheet (SDS) provided with SKU C194823 for confirmed temperature ranges and specific storage requirements for your lot.

How can I verify the purity and identity of the compound upon receipt?

Purity and identity can be confirmed using HPLC (UV detection ~254 nm), ¹H NMR (characteristic aromatic, methyl, and COOH signals), IR spectroscopy (nitrile stretch ~2230 cm⁻¹, carbonyl ~1680–1720 cm⁻¹), and mass spectrometry ([M–H]⁻ at m/z 160.05). Additionally, request the lot-specific Certificate of Analysis (CoA) from Aladdin Scientific at the time of ordering SKU C194823.

Is 4-Cyano-3-methylbenzoic acid compatible with standard amide coupling conditions?

Yes, the carboxylic acid group of 4-cyano-3-methylbenzoic acid is compatible with commonly used amide coupling reagents such as EDC/HOBt, HATU, and DCC/NHS under standard conditions. The nitrile and methyl groups are generally stable to these mild coupling conditions. Researchers should optimise reaction conditions for their specific substrate and application.

Where can I obtain the Safety Data Sheet (SDS) for this product?

The SDS for 4-Cyano-3-methylbenzoic acid (SKU C194823) is available through the Aladdin Scientific website on the product page. You may also contact Aladdin Scientific customer service to request the document directly. Always review the SDS before first use to ensure safe handling in your laboratory.

References

1. Aladdin Scientific. Product datasheet and Certificate of Analysis for 4-Cyano-3-methylbenzoic acid, SKU C194823. Aladdin Scientific; [date to be confirmed].
2. Aladdin Scientific. Safety Data Sheet (SDS) for 4-Cyano-3-methylbenzoic acid, SKU C194823. Aladdin Scientific; [date to be confirmed].
3. Clayden J, Greeves N, Warren S. Organic Chemistry. 2nd ed. Oxford University Press; 2012. [General reference for nitrile and carboxylic acid reactivity.]

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