Methyl 5-Iodo-2,4-Dimethylbenzoate: Properties & Lab Guide
Methyl 5-Iodo-2,4-Dimethylbenzoate: Properties & Lab Guide
Methyl 5-iodo-2,4-dimethylbenzoate is a halogenated aromatic ester widely employed as a versatile building block in palladium-catalyzed cross-coupling reactions and other transition-metal-mediated transformations in synthetic organic chemistry.
- Chemical Name
- Methyl 5-iodo-2,4-dimethylbenzoate
- Molecular Formula
- C₁₀H₁₁IO₂
- Molecular Weight
- 290.10 g/mol
- Functional Groups
- Aryl iodide, methyl ester, two methyl substituents
- Primary Application
- Building block in cross-coupling reactions (Suzuki, Sonogashira, Heck, etc.)
- Storage Condition
- Store in a cool, dry, well-ventilated area away from light and moisture
- Aladdin SKU
- M732240
Chemical Identity and Physicochemical Properties
Methyl 5-iodo-2,4-dimethylbenzoate (SKU: M732240) is an organoiodine compound belonging to the class of halogenated aromatic esters. Its molecular formula is C₁₀H₁₁IO₂ with a molecular weight of approximately 290.10 g/mol. The structure features a benzoate methyl ester at the 1-position, methyl substituents at the 2- and 4-positions, and an iodo substituent at the 5-position of the benzene ring.
The steric environment created by the two ortho- and para-methyl groups influences the reactivity of both the aryl iodide and the ester moiety, making selectivity in downstream functionalization reactions an important design consideration. The aryl C–I bond (bond dissociation energy lower than C–Br and C–Cl) renders this compound highly reactive in oxidative addition steps of palladium and copper catalytic cycles.
Note: Specific physical constants such as melting point, boiling point, and density are not provided in the current source material and should be verified against the certificate of analysis (CoA) supplied with the product lot.
Synthetic Applications and Reaction Protocols
The aryl iodide functionality in Methyl 5-iodo-2,4-dimethylbenzoate makes it an excellent electrophilic partner in a broad spectrum of transition-metal-catalyzed coupling reactions:
- Suzuki–Miyaura Coupling: Reacts with arylboronic acids in the presence of a Pd(0) or Pd(II) catalyst and base (e.g., K₂CO₃, Cs₂CO₃) in aqueous/organic solvent mixtures to yield biaryl products.
- Sonogashira Coupling: Couples with terminal alkynes using Pd/Cu co-catalysis to install alkyne linkers, valuable in pharmaceutical and materials chemistry.
- Heck Reaction: Undergoes Pd-catalyzed olefination with electron-rich or electron-neutral alkenes.
- Buchwald–Hartwig Amination: The aryl iodide can be employed for C–N bond formation under Pd catalysis with appropriate ligands.
- Directed Metalation / Halogen–Metal Exchange: The C–I bond can participate in lithium–halogen exchange at low temperature (–78 °C) to generate a reactive aryllithium species for nucleophilic addition.
The methyl ester group provides an additional handle for further elaboration: saponification yields the corresponding carboxylic acid, and reduction (e.g., LiAlH₄, DIBAL-H) affords the benzyl alcohol derivative. Researchers should design reaction sequences to exploit functional group orthogonality between the aryl iodide and the ester.
Specific yields, conditions, and substrate scope should be confirmed with primary literature or internal optimization; see review_flags for detail.
Handling, Safety, and Storage Guidelines
Personal Protective Equipment (PPE): When handling Methyl 5-iodo-2,4-dimethylbenzoate, wear appropriate chemical-resistant gloves (e.g., nitrile), safety glasses or goggles, and a laboratory coat. Work in a well-ventilated fume hood to minimize inhalation exposure.
Storage: Store in a tightly sealed container in a cool (room temperature or below), dry, and well-ventilated location, away from direct light, moisture, and incompatible materials such as strong oxidizers and strong bases. Prolonged exposure to moisture or light may cause degradation of the aryl iodide moiety.
Disposal: Dispose of waste material in accordance with local, regional, and national regulations for halogenated organic compounds. Do not pour down the drain.
First Aid: In case of skin or eye contact, flush immediately with copious amounts of water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air.
Consult the Safety Data Sheet (SDS) for complete hazard classification, GHS pictograms, and regulatory information before use. Specific GHS hazard and precautionary statements for this compound are not detailed in the current source material and should be obtained from the product SDS.
Quality, Purity, and Ordering Information
Aladdin Scientific offers Methyl 5-iodo-2,4-dimethylbenzoate under SKU M732240. Researchers and procurement teams should request the Certificate of Analysis (CoA) for the specific lot number to confirm purity (typically verified by GC, HPLC, or NMR), identity (confirmed by NMR, IR, or MS), and any residual solvent or heavy metal specifications relevant to their application.
When evaluating suitability for sensitive catalytic applications (e.g., Pd-catalyzed coupling), high purity grades are recommended to avoid catalyst poisoning from trace impurities. Contact Aladdin Scientific's technical support team for bulk quantities, custom purity grades, or additional analytical data.
Exact purity specifications and available pack sizes are not listed in the current source material; please refer to the product page or contact Aladdin directly for up-to-date specifications and pricing.
Frequently asked questions
What types of cross-coupling reactions is Methyl 5-iodo-2,4-dimethylbenzoate suitable for?
Methyl 5-iodo-2,4-dimethylbenzoate is well-suited for Suzuki–Miyaura, Sonogashira, Heck, and Buchwald–Hartwig reactions due to its reactive aryl C–I bond. It can also undergo lithium–halogen exchange at low temperatures for nucleophilic addition applications. The methyl ester group remains orthogonal under many standard coupling conditions.
How should Methyl 5-iodo-2,4-dimethylbenzoate be stored to maintain stability?
Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area away from direct light and moisture. Prolonged exposure to light or humidity may lead to degradation of the aryl iodide group. Always refer to the product SDS and CoA for lot-specific storage recommendations.
Can the methyl ester group in this compound be further modified?
Yes. The methyl ester can be hydrolyzed under basic conditions (saponification) to yield the corresponding carboxylic acid, or reduced with reagents such as LiAlH₄ or DIBAL-H to afford the benzyl alcohol. These transformations allow researchers to diversify the compound into a range of intermediates for medicinal chemistry or materials science applications.
How do I confirm the purity and identity of the Aladdin lot I received?
Request the Certificate of Analysis (CoA) for your specific lot number from Aladdin Scientific. The CoA typically includes purity data from GC, HPLC, or NMR analysis, along with identity confirmation by spectroscopic methods. For critical applications, in-house verification by ¹H NMR or LC-MS is recommended.
References
- Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007
- Sonogashira, K. Development of Pd–Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides. J. Organomet. Chem. 2002, 653, 46–49. doi:10.1016/S0022-328X(02)01158-0
- Heck, R. F.; Nolley, J. P. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J. Org. Chem. 1972, 37, 2320–2322. doi:10.1021/jo00979a024
- Aladdin Scientific. Product Page: Methyl 5-iodo-2,4-dimethylbenzoate, SKU M732240.
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