Production Method 1

1459-93-4

73183-34-3

944392-68-1

Reaction Conditions

1.1 Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium ,  N1-[4,4′-Bis(1,1-dimethylethyl)[2,2′-bipyridin]-6-yl]-1,2-benzenediamine Solvents: Cyclopentyl methyl ether ;  12 h, 140 °C

Reference

NNB-type tridentate boryl ligands enabling a highly active iridium catalyst for C-H borylation

Ding, Siyi ; Wang, Linghua; Miao, Zongcheng; Li, Pengfei, Molecules, 2019, 24(7),

Production Method 2

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: stereoisomer of Bis[2-[[bis[2,4-bis(1,1-dimethylethyl)phenoxy]phosphino-κP]oxy]-… ,  4-(9-Anthracenyl)-3-(1,1-dimethylethyl)-2,3-dihydro-1,3-benzoxaphosphole Solvents: Dimethylacetamide ;  12 h, 100 °C

Reference

Efficient Monophosphorus Ligands for Palladium-Catalyzed Miyaura Borylation

Tang, Wenjun; Keshipeddy, Santosh; Zhang, Yongda; Wei, Xudong; Savoie, Jolaine; et al, Organic Letters, 2011, 13(6), 1366-1369

Production Method 3

1459-93-4

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Isopropanol ,  Chloro[(1,2,5,6-η)-1,5-cyclooctadiene](1,10-phenanthroline-κN1,κN10)iridium Solvents: Heptane ;  1 h, 75 °C
1.2 18 h

Reference

Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics

Slack, Eric D.; Colacot, Thomas J., Organic Letters, 2021, 23(5), 1561-1565

Production Method 4

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Palladium diacetate Solvents: Dimethylformamide ;  24 h, rt → 90 °C

Reference

A Novel Electrochromic Polymer Synthesized through Electropolymerization of a New Donor-Acceptor Bipolar System

Natera, Jose; Otero, Luis; Sereno, Leonides; Fungo, Fernando; Wang, Nung-Sen; et al, Macromolecules (Washington, 2007, 40(13), 4456-4463

Production Method 5

51839-15-7

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Palladium diacetate Solvents: Dimethylformamide ;  12 h, rt → 90 °C; 90 °C → rt

Reference

Functionalized mesopores to metal organic frameworks via metal ligand fragment coassembly

Park, Jinhee; Wang, Zhiyong U.; Sun, Lin-Bing; Chen, Ying-Pin; Zhou, Hong-Cai, Journal of the American Chemical Society, 2012, 134(49), 20110-20116

Production Method 6

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

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

Reference

Two isostructural metal-organic frameworks with unique nickel clusters for C2H2/C2H6/C2H4 mixture separation

Wang, Hao-Tian; Chen, Qiang; Zhang, Xin; Zhao, Yan-Long; Xu, Ming-Ming; et al, Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2022, 10(23), 12497-12502

Production Method 7

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichlorobis[(diphenylphosphino)ferrocene]palladium Solvents: 1,4-Dioxane ;  24 h, 80 °C

Reference

A new metal-organic framework for separation of C2H2/CH4 and CO2/CH4 at room temperature

Duan, Xing; Zhou, You; Lv, Ran; Yu, Ben; Chen, Haodong; et al, Journal of Solid State Chemistry, 2018, 260, 31-33

Production Method 8

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  24 h, 70 °C

Reference

A Copper(II)-Paddlewheel Metal-Organic Framework with Exceptional Hydrolytic Stability and Selective Adsorption and Detection Ability of Aniline in Water

Chen, Ya ; Wang, Bin; Wang, Xiaoqing; Xie, Lin-Hua ; Li, Jinping ; et al, ACS Applied Materials & Interfaces, 2017, 9(32), 27027-27035

Production Method 9

1459-93-4

73183-34-3

944392-68-1

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  1,1′,3,3′-Tetrahydro-1,1′-di-2-pyridinyl-2,2′-bi-2H-1,3,2-benzodiazaborole Solvents: Cyclopentyl methyl ether ;  16 h, 100 °C; 100 °C → rt

Reference

Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation

Wang, Guanghui; Xu, Liang; Li, Pengfei, Journal of the American Chemical Society, 2015, 137(25), 8058-8061

Production Method 10

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  24 h, 80 °C

Reference

A NbO-type metal-organic framework exhibiting high deliverable capacity for methane storage

Song, Chengling; Ling, Yajing; Feng, Yunlong; Zhou, Wei; Yildirim, Taner; et al, Chemical Communications (Cambridge, 2015, 51(40), 8508-8511

Production Method 11

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  24 h, 80 °C

Reference

Compositions and methods for selective separation of hydrocarbon isomers

, World Intellectual Property Organization, , ,

Production Method 12

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  24 h, 128 °C

Reference

Preparation of 5-[2-(5-carboxy-pyridyl)]-1,3- benzene dicarboxylic acid

, China, , ,

Production Method 13

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  24 h, rt → 80 °C

Reference

Synthesis of metal organic framework (mof) materials with high adsorption capacity of organic compounds and CO2 capture

, World Intellectual Property Organization, , ,

Production Method 14

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: 1,1-Bis(diphenylphosphino)ferrocene ,  Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  18 h, 90 °C

Reference

Preparation of 3-oxo-2,3-dihydropyridazin-4-ylurea derivatives as PDE4 inhibitors

, World Intellectual Property Organization, , ,

Production Method 15

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  -78 °C; 15 h, reflux

Reference

Methane Storage in Metal-Organic Frameworks: Current Records, Surprise Findings, and Challenges

Peng, Yang; Krungleviciute, Vaiva; Eryazici, Ibrahim; Hupp, Joseph T.; Farha, Omar K.; et al, Journal of the American Chemical Society, 2013, 135(32), 11887-11894

Production Method 16

51839-15-7

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Palladium diacetate Solvents: Dimethylformamide

Reference

Programmed Negative Allostery with Guest-Selected Rotamers Control Anion-Anion Complexes of Stackable Macrocycles

Sheetz, Edward G.; Qiao, Bo; Pink, Maren; Flood, Amar H., Journal of the American Chemical Society, 2018, 140(25), 7773-7777

Production Method 17

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  rt → 100 °C; 12 h, 100 °C

Reference

Method for preparing 5-(4-carboxynaphthalen-1-yl)isophthalic acid from 4-bromonaphthalen-1-carboxylic acid

, China, , ,

Production Method 18

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  0.5 h; 12 h, rt → 100 °C

Reference

A synthetic method of new 5-[10-(9-carboxyl anthracene)]-isophthalic acid

, China, , ,

Production Method 19

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

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

Reference

A New Multidentate Hexacarboxylic Acid for the Construction of Porous Metal-Organic Frameworks of Diverse Structures and Porosities

Chen, Zhenxia; Xiang, Shengchang; Liao, Tengbiao; Yang, Yongtai; Chen, Yu-Sheng; et al, Crystal Growth & Design, 2010, 10(6), 2775-2779

Production Method 20

51760-21-5

73183-34-3

944392-68-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  24 h, 70 °C

Reference

A novel methoxy-decorated metal-organic framework exhibiting high acetylene and carbon dioxide storage capacities

Duan, Xing; Cui, Yuanjing; Yang, Yu; Qian, Guodong, CrystEngComm, 2017, 19(11), 1464-1469

Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate Raw materials

• Dimethyl 5-iodoisophthalate
• 1,3-dimethyl 5-bromobenzene-1,3-dicarboxylate
• Dimethyl isophthalate
• Bis(pinacolato)diborane

Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate Preparation Products

• Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate (944392-68-1)

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  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Phthalic acid and derivatives
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate: A Versatile Compound in Modern Pharmaceutical Research

Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate (CAS No. 944392-68-1) is a highly versatile compound that has gained significant attention in the field of pharmaceutical research and development. This compound belongs to the class of boronic esters and is characterized by its unique structural features and chemical properties. In this article, we will delve into the chemical structure, synthesis methods, applications, and recent advancements in the study of this compound.

The chemical structure of Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate is particularly noteworthy. The compound consists of an isophthalate core with a boronic ester moiety attached at the 5-position. The presence of the boronic ester group imparts unique reactivity and functional properties to the molecule. Specifically, the boronic ester group can undergo various chemical transformations such as Suzuki-Miyaura coupling reactions, which are widely used in the synthesis of complex organic molecules and pharmaceuticals.

The synthesis of Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate has been extensively studied and optimized to achieve high yields and purity. One common synthetic route involves the reaction of dimethyl isophthalate with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane) in the presence of a suitable catalyst. This method provides a straightforward and efficient way to access the target compound. Recent advancements in catalytic systems have further improved the efficiency and selectivity of this reaction, making it more suitable for large-scale production.

In terms of applications, Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate has found numerous uses in pharmaceutical research. One of its primary applications is as an intermediate in the synthesis of bioactive compounds. The boronic ester group can be readily converted into other functional groups through various chemical transformations, allowing for the construction of complex molecular architectures. This versatility makes it an invaluable tool in drug discovery and development.

Recent studies have also explored the potential of Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate in drug delivery systems. The unique properties of boronic esters enable them to form reversible covalent bonds with certain biomolecules such as sugars and proteins. This property can be exploited to design targeted drug delivery systems that release their payload under specific physiological conditions. For example, researchers have demonstrated that boronic ester-based prodrugs can be activated by glucose in diabetic patients, leading to improved therapeutic outcomes.

The pharmacological properties of compounds derived from Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isophthalate have also been investigated. Studies have shown that these compounds exhibit a range of biological activities including anti-inflammatory and anticancer effects. For instance, a recent study published in the Journal of Medicinal Chemistry reported that a derivative of this compound showed potent inhibitory activity against cancer cell lines while demonstrating low toxicity towards normal cells.

In addition to its applications in drug discovery and delivery systems, Dimethyl 5-(4,4，5，5-tetramethyl-1，3，2-dioxaborolan-2-YL)isophthalate has also been explored for its potential use in materials science. The unique reactivity and functional properties of boronic esters make them attractive candidates for the development of advanced materials such as polymers and coatings. Recent research has focused on incorporating boronic ester moieties into polymer backbones to create materials with tunable properties such as self-healing capabilities and stimuli-responsive behavior.

The safety profile of Dimethyl 5-(4，4，5，5-tetramethyl-1，3，2-dioxaborolan-2-YL)isophthalate is another important consideration in its use for pharmaceutical applications. Extensive toxicological studies have shown that this compound exhibits low toxicity when handled properly under laboratory conditions. However, proper safety protocols should always be followed when working with any chemical compound to ensure the well-being of researchers and laboratory personnel.

In conclusion, Dimethyl 5-(4，4，5，5-tetramethyl-1，3，2-dioxaborolan-2-YL)isophthalate (CAS No. 944392-68-1) is a highly versatile compound with significant potential in pharmaceutical research and development. Its unique chemical structure and reactivity make it an invaluable tool for synthesizing complex bioactive molecules and designing advanced drug delivery systems. Ongoing research continues to uncover new applications and properties of this compound, highlighting its importance in modern chemistry and biology.

• 171364-80-0(Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 480425-35-2(methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 903895-48-7(3-t-Butoxycarbonylphenylboronic acid, pinacol ester)
• 1218791-30-0(3-(Isopropoxycarbonyl)-5-methylphenylboronic acid, pinacol ester)
• 17136-80-0(METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE)
• 195062-62-5(4-Ethoxycarbonylphenylboronic acid, pinacol ester)
• 882679-40-5(Methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoate)
• 269410-00-6(Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 929626-17-5(Methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 1150271-63-8(3-(Ethoxycarbonyl)-5-methylphenylboronic Acid Pinacol Ester)