Production Method 1

165803-89-4

90347-66-3

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Potassium carbonate ,  Cobalt oxide (Co3O4) (on modified Vulcan XC72R support formed by pyrolysis with nitrogen-ligated cobalt(II) acetate complexes) ;  24 h, 1 bar, 60 °C

Reference

Selective Oxidation of Alcohols to Esters Using Heterogeneous Co3O4-N@C Catalysts under Mild Conditions

Jagadeesh, Rajenahally V.; Junge, Henrik; Pohl, Marga-Martina; Radnik, Joerg; Brueckner, Angelika; et al, Journal of the American Chemical Society, 2013, 135(29), 10776-10782

Production Method 2

82998-57-0

90347-66-3

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol ,  Water

Reference

The Use of Palladium Catalysis for the Formation of Fused Aromatic Compounds and for the Diastereoselective Formate Reduction of Allylic Carbonates

Paquin, Jean-Francois, 2004, , ,

Production Method 3

82998-57-0

90347-66-3

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Methanol ;  19 h, reflux; cooled

Reference

Rapid synthesis of Abelson tyrosine kinase inhibitors using click chemistry

Kalesh, Karunakaran A.; Liu, Kai; Yao, Shao Q., Organic & Biomolecular Chemistry, 2009, 7(24), 5129-5136

Production Method 4

82998-57-0

18107-18-1

90347-66-3

Reaction Conditions

1.1 Solvents: Methanol ,  Benzene ,  Hexane ;  rt; 10 min, rt

Reference

C3 Halogen and C8'' Substituents on Stilbene Arotinoids Modulate Retinoic Acid Receptor Subtype Function

Alvarez, Susana; Khanwalkar, Harshal; Alvarez, Rosana; Erb, Cathie; Martinez, Claudio; et al, ChemMedChem, 2009, 4(10), 1630-1640

Production Method 5

82998-57-0

90347-66-3

Reaction Conditions

1.1 Catalysts: Sulfuric acid ;  24 h, 65 °C; cooled

Reference

Design, Synthesis, and Structure-Activity Relationship Studies of 3-(Phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine Derivatives as a New Class of Src Inhibitors with Potent Activities in Models of Triple Negative Breast Cancer

Zhang, Chun-Hui; Zheng, Ming-Wu; Li, Ya-Ping; Lin, Xing-Dong; Huang, Mei; et al, Journal of Medicinal Chemistry, 2015, 58(9), 3957-3974

Production Method 6

82998-57-0

90347-66-3

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Methanol

Reference

Palladium-Catalyzed Sequential Alkylation-Alkenylation Reactions and Their Application to the Synthesis of Fused Aromatic Rings

Lautens, Mark; Paquin, Jean-Francois; Piguel, Sandrine; Dahlmann, Marc, Journal of Organic Chemistry, 2001, 66(24), 8127-8134

Production Method 7

99-75-2

90347-66-3

Reaction Conditions

1.1 Reagents: Iodine ,  Sodium periodate Solvents: Acetic acid ,  Acetic anhydride ;  5 - 10 °C
1.2 Reagents: Sulfuric acid ;  5 - 10 °C
1.3 5 - 10 °C; 1 h, rt; 4 h, 40 °C

Reference

Enantiomerically Pure Axially Chiral Aminocarbene Complexes of Chromium

Meca, Ludek; Cisarova, Ivana; Drahonovsky, Dusan; Dvorak, Dalimil, Organometallics, 2008, 27(8), 1850-1858

Production Method 8

82998-57-0

90347-66-3

Reaction Conditions

1.1 Reagents: Hydrogen ion ;  reflux

Reference

Solvolysis of 2-chloro-2(3,4-disubstituted) phenylpropanes: Validity of Hammett-Brown σ+ constants in assessing additive effects of substituents

Taha, Ahmed A., International Journal of Chemical Kinetics, 2012, 44(8), 514-523

Production Method 9

18595-18-1

90347-66-3

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Water ;  0 °C; 2 h, 0 °C
1.2 Reagents: Potassium iodide Solvents: Water ;  0 °C → rt
1.3 Reagents: Sodium thiosulfate Solvents: Water

Reference

Design, Synthesis, and Biological Evaluation of 3-(Imidazo[1,2-a]pyrazin-3-ylethynyl)-4-isopropyl-N-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide as a Dual Inhibitor of Discoidin Domain Receptors 1 and 2

Wang, Zhen; Zhang, Yali; Pinkas, Daniel M.; Fox, Alice E.; Luo, Jinfeng; et al, Journal of Medicinal Chemistry, 2018, 61(17), 7977-7990

Methyl 3-iodo-4-methylbenzoate Raw materials

• 3-Iodo-4-methylbenzoic acid
• methyl 3-amino-4-methyl-benzoate
• Methyl p-Toluate
• (diazomethyl)trimethylsilane
• 3-Iodo-4-methylbenzyl Alcohol

Methyl 3-iodo-4-methylbenzoate Preparation Products

• Methyl 3-iodo-4-methylbenzoate (90347-66-3)

• 1. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782
• 2. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 3. An aquatic host–guest complex between a supramolecular G-quadruplex and the anticancer drug doxorubicin?
  José M. Rivera,Mariana Martín-Hidalgo,Jean C. Rivera-Ríos Org. Biomol. Chem., 2012,10, 7562-7565
• 4. An anti-leakage liquid metal thermal interface material
  Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng Chu RSC Adv., 2020,10, 18824-18829
• 5. An all-solid-state imprinted polymer-based potentiometric sensor for determination of bisphenol S?
  Rongning Liang,Tanji Yin,Ruiqing Yao,Wei Qin RSC Adv., 2016,6, 73308-73312

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acid esters
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Benzoic acid esters
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Methyl 3-iodo-4-methylbenzoate (CAS No. 90347-66-3) in Modern Chemical and Pharmaceutical Research

Methyl 3-iodo-4-methylbenzoate, identified by the CAS number 90347-66-3, is a specialized organic compound that has garnered significant attention in the fields of synthetic chemistry and pharmaceutical research. This compound, characterized by its unique structural motif—a benzene ring substituted with an iodo group at the 3-position and a methyl group at the 4-position—holds considerable potential for various applications, particularly in the development of novel bioactive molecules. The presence of the iodo substituent makes it a valuable intermediate in cross-coupling reactions, which are pivotal in constructing complex molecular architectures essential for drug discovery.

The significance of Methyl 3-iodo-4-methylbenzoate lies in its versatility as a building block. In recent years, there has been a surge in research focused on developing efficient synthetic methodologies for aryl iodides, given their widespread use in Suzuki-Miyaura, Heck, and Buchwald-Hartwig couplings. These reactions are fundamental to constructing biaryl systems, which are prevalent in many pharmacologically active compounds. The methyl benzoate moiety further enhances its utility by providing a facile entry point for further functionalization through ester hydrolysis or transesterification, allowing chemists to tailor the compound’s properties for specific applications.

Recent advancements in pharmaceutical chemistry have highlighted the importance of halogenated aromatic compounds in medicinal design. The iodo group in Methyl 3-iodo-4-methylbenzoate serves as an excellent handle for palladium-catalyzed transformations, enabling the introduction of diverse substituents at other positions on the benzene ring. This flexibility is particularly valuable in drug discovery pipelines, where rapid and efficient diversification of molecular libraries is crucial for identifying lead compounds with desired biological activity. For instance, studies have demonstrated its utility in generating substituted benzoates that exhibit antimicrobial and anti-inflammatory properties, underscoring its relevance in therapeutic research.

The compound’s structural features also make it an attractive candidate for material science applications. Functionalized aromatic compounds are increasingly being explored for their potential in organic electronics, photovoltaics, and catalysis. The electron-withdrawing nature of the iodo group can modulate the electronic properties of the benzene ring, making it suitable for designing molecules with tailored optoelectronic characteristics. Moreover, the ester functionality provides a site for further chemical manipulation, allowing for the synthesis of polymers or liquid crystals with enhanced performance.

In terms of synthetic methodology, Methyl 3-iodo-4-methylbenzoate has been employed in various multi-step syntheses. One notable example is its use as an intermediate in the preparation of complex heterocyclic frameworks. By participating in cyclization reactions or serving as a precursor to more intricate structures, this compound contributes to the construction of molecules with potential biological relevance. The ability to introduce additional functional groups through cross-coupling or other transformations makes it a cornerstone in modern synthetic strategies.

The pharmaceutical industry has also leveraged Methyl 3-iodo-4-methylbenzoate in structure-activity relationship (SAR) studies. By systematically modifying its substituents and examining changes in biological activity, researchers can gain insights into how specific structural features influence a molecule’s efficacy and selectivity. Such studies are critical for optimizing drug candidates and improving their pharmacokinetic profiles. The compound’s well-defined reactivity profile ensures that these investigations can be conducted efficiently and reliably.

Looking ahead, the future prospects of Methyl 3-iodo-4-methylbenzoate are promising. As synthetic techniques continue to evolve, new methods for accessing this intermediate will likely emerge, further expanding its utility. Additionally, advances in computational chemistry may enable more precise predictions of its reactivity and applications, streamlining drug discovery efforts. Collaborative efforts between academia and industry will be essential to fully harness its potential across multiple domains.

In conclusion, Methyl 3-iodo-4-methylbenzoate (CAS No. 90347-66-3) represents a versatile and valuable compound with broad applications in chemical synthesis and pharmaceutical research. Its unique structural features and reactivity make it an indispensable tool for constructing complex molecules with therapeutic potential. As research progresses, this compound will undoubtedly continue to play a pivotal role in advancing both academic understanding and industrial innovation.

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