Production Method 1

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  overnight, rt → 100 °C

Reference

Preparation of heteroaryl compounds as influenza virus replication inhibitors

, World Intellectual Property Organization, , ,

Production Method 2

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  9 h, 110 °C

Reference

Catalytic Synthesis of Atropisomeric o-Terphenyls with 1,2-Diaxes via Axial-to-Axial Diastereoinduction

Gao, Qianwen; Wu, Chenggui; Deng, Shuang; Li, Lisha; Liu, Ze-Shui; et al, Journal of the American Chemical Society, 2021, 143(19), 7253-7260

Production Method 3

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Triphenylphosphine ,  Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  29 h, 100 °C

Reference

Preparation of oxadiazolidinedione compounds as GPR40 receptor agonists

, World Intellectual Property Organization, , ,

Production Method 4

955929-54-1

Reaction Conditions

Reference

Preparation of thiazolidinedione compounds as agonists of GPR40 receptor

, Japan, , ,

Production Method 5

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  3 h, 85 °C

Reference

Compound having pd-l1 inhibitory activity, preparation method therefor and use thereof

, World Intellectual Property Organization, , ,

Production Method 6

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  overnight, 110 °C

Reference

Symmetric or semi-symmetric compounds useful as immunomodulators

, World Intellectual Property Organization, , ,

Production Method 7

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Dimethyl sulfoxide ;  rt; overnight, 120 °C

Reference

Preparation of benzoic acid derivatives for treatment of metabolic and liver diseases

, World Intellectual Property Organization, , ,

Production Method 8

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  16 h, 90 °C; 90 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Benzoxaboroles - Novel autotaxin inhibitors

Kraljic, Kristina; Jelic, Dubravko; Ziher, Dinko; Cvrtila, Adam; Dragojevic, Snjezana; et al, Molecules, 2019, 24(19),

Production Method 9

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  16 h, 100 °C

Reference

Biaryl compounds as immune checkpoint inhibitors, compositions and methods for preparation

, World Intellectual Property Organization, , ,

Production Method 10

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Triphenylphosphine ,  Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  29 h, 100 °C

Reference

Preparation of tetrazole compounds as GPR40 agonists

, World Intellectual Property Organization, , ,

Production Method 11

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Triphenylphosphine ,  Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  29 h, 100 °C

Reference

Preparation of carboxylic acid compounds as GPR40 agonists

, World Intellectual Property Organization, , ,

Production Method 12

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Triphenylphosphine ,  Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  29 h, 100 °C

Reference

Preparation of thiazolidinedione compounds as agonists of GPR40 receptor

, World Intellectual Property Organization, , ,

Production Method 13

73183-34-3

99548-54-6

955929-54-1

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Triphenylphosphine ,  Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  3 d, 100 °C

Reference

Preparation of 2-benzyl-1,2,4-oxadiazolidinedione compounds as agonists of G protein-coupled receptor 40 (GPR40) and insulin-secretion enhancers

, World Intellectual Property Organization, , ,

Production Method 14

955929-54-1

Reaction Conditions

Reference

Preparation of tetrazole compounds as GPR40 agonists

, Japan, , ,

Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Raw materials

• Bis(pinacolato)diborane
• Methyl 3-bromo-2-methylbenzoate

Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Preparation Products

• Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (955929-54-1)

• 1. Evidence of rutile-to-anatase photo-induced electron transfer in mixed-phase TiO2 by solid-state NMR spectroscopy?
  Weili Dai,Guangjun Wu,Michael Hunger Chem. Commun., 2015,51, 13779-13782
• 2. Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides
  Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat Veisi New J. Chem., 2018,42, 1757-1761
• 3. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130
• 4. Distinction of trans–cis photoisomers with comparable optical properties in multiple-state photochromic systems – examining a molecule with three azobenzenes via in situ irradiation NMR spectroscopy?
  Jonas Kind,Lukas Kaltschnee,Martin Leyendecker,Christina M. Thiele Chem. Commun., 2016,52, 12506-12509
• 5. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845

• 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

Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS No. 955929-54-1): A Versatile Boronic Ester in Modern Chemistry

Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS 955929-54-1) is a highly valuable boronic ester compound that has gained significant attention in pharmaceutical research and organic synthesis. This white to off-white crystalline powder belongs to the class of aryl boronic esters, which are crucial intermediates in Suzuki-Miyaura cross-coupling reactions - one of the most important carbon-carbon bond forming reactions in modern organic chemistry.

The molecular structure of this compound features both a methyl benzoate moiety and a pinacol boronic ester group, making it particularly useful for various synthetic applications. With a molecular formula of C₁₅H₂₁BO₄ and molecular weight of 276.14 g/mol, this compound demonstrates excellent stability under normal conditions, which contributes to its widespread use in laboratory settings.

Recent trends in medicinal chemistry have shown growing interest in boron-containing compounds, particularly due to their applications in drug discovery and development. The Methyl 2-methyl-3-(pinacol boronate)benzoate derivative serves as a key building block for creating more complex molecules with potential biological activities. Researchers are particularly interested in how this compound's boronic acid functionality can be utilized in the development of protease inhibitors and other therapeutic agents.

In synthetic chemistry, this compound is frequently employed in palladium-catalyzed coupling reactions, where its aryl boronic ester group participates in forming new carbon-carbon bonds. The presence of the methyl ester group offers additional synthetic flexibility, allowing for further functionalization through hydrolysis or reduction. These properties make CAS 955929-54-1 particularly valuable for constructing complex molecular architectures found in many modern pharmaceuticals and materials.

The stability of the 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacol boronic ester) protecting group is one of the key advantages of this compound. Unlike free boronic acids, which can be prone to protodeboronation and other decomposition pathways, the pinacol ester form offers enhanced stability while maintaining reactivity in cross-coupling reactions. This characteristic has made Methyl 2-methyl-3-(pinacol boronate)benzoate a preferred choice for many synthetic chemists working on complex multi-step syntheses.

From a commercial perspective, the demand for boronic ester intermediates like 955929-54-1 has been steadily increasing, driven by the growing pharmaceutical industry and the continuous development of new therapeutic compounds. The compound's role in creating biaryl structures - common motifs in many drugs - makes it particularly valuable. Market analysis shows that boronic acid derivatives represent one of the fastest-growing segments in fine chemicals, with projected compound annual growth rates exceeding 8% through 2028.

Quality control aspects of Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate typically involve HPLC analysis to ensure high purity (>97%), along with standard spectroscopic characterization including ¹H NMR, ¹³C NMR, and mass spectrometry. The compound's stability allows for long-term storage under appropriate conditions (typically 2-8°C in a dry environment), making it convenient for laboratory use and commercial distribution.

Environmental and safety considerations for this compound are generally favorable compared to many other synthetic intermediates. As a boronic ester, it doesn't exhibit the same level of reactivity as some other organometallic compounds, though standard laboratory precautions should still be observed. The growing focus on green chemistry has led to increased interest in developing more sustainable versions of Suzuki coupling reactions using compounds like 955929-54-1, with researchers exploring aqueous reaction conditions and recyclable catalyst systems.

Future research directions for this compound class include exploration of its potential in materials science applications, particularly in the development of organic electronic materials and metal-organic frameworks (MOFs). The unique electronic properties of the aryl boronic ester moiety may offer interesting possibilities for designing new functional materials with tailored properties.

In conclusion, Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS 955929-54-1) represents an important tool in modern synthetic chemistry, with wide-ranging applications in pharmaceutical development and materials science. Its combination of stability, reactivity, and synthetic versatility ensures its continued importance in chemical research and industrial applications for years to come.

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