Production Method 1

662112-12-1

73183-34-3

916587-44-5

Reaction Conditions

1.1 Reagents: Lithium carbonate (Li2CO3) Catalysts: Tributylphosphine ,  Bis(1,5-cyclooctadiene)nickel Solvents: 1,4-Dioxane ;  36 h, 160 °C

Reference

Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates

Guo, Lin; et al, Chemistry - A European Journal, 2016, 22(47), 16787-16790

Production Method 2

1480491-24-4

73183-34-3

916587-44-5

Reaction Conditions

1.1 Reagents: Cesium fluoride Catalysts: Bis(1,5-cyclooctadiene)nickel ,  Tricyclohexylphosphine ,  Cuprous iodide Solvents: Toluene ;  1 min, rt; 24 h, 80 °C

Reference

Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes for Diverse C-F Bond Functionalizations

Niwa, Takashi; et al, Journal of the American Chemical Society, 2015, 137(45), 14313-14318

Production Method 3

24424-99-5

60577-34-6

916587-44-5

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  overnight, reflux
2.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: Dimethyl sulfoxide ;  3.5 h, 80 °C; 80 °C → rt

Reference

Computer-guided design of a Cu(II) receptor and sensor

Lin, Chen; et al, New Journal of Chemistry, 2006, 30(12), 1725-1730

Production Method 4

73183-34-3

1655508-79-4

916587-44-5

Reaction Conditions

1.1 Catalysts: Tricyclohexylphosphine ,  Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-hydroxydirhodium Solvents: Hexane ;  1 h, 80 °C; 80 °C → rt
1.2 Solvents: Hexane ;  12 h, 80 °C

Reference

Rhodium-catalyzed ipso-borylation of alkylthioarenes via C-S bond cleavage

Uetake, Yuta; et al, Organic Letters, 2016, 18(11), 2758-2761

Production Method 5

73183-34-3

306768-12-7

916587-44-5

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: Dimethyl sulfoxide ;  3.5 h, 80 °C; 80 °C → rt

Reference

Computer-guided design of a Cu(II) receptor and sensor

Lin, Chen; et al, New Journal of Chemistry, 2006, 30(12), 1725-1730

4-(BOC-Methylamino)phenylboronic acid, pinacol ester Raw materials

• Di-tert-butyl dicarbonate
• 4-Iodo-N-methylaniline
• Benzoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-, phenyl ester
• TERT-BUTYL N-(4-FLUOROPHENYL)-N-METHYLCARBAMATE
• Bis(pinacolato)diborane
• Carbamic acid, N-methyl-N-[4-(methylthio)phenyl]-, 1,1-dimethylethyl ester
• N-Boc 4-Iodo-N-Methylaniline

4-(BOC-Methylamino)phenylboronic acid, pinacol ester Preparation Products

• 4-(BOC-Methylamino)phenylboronic acid, pinacol ester (916587-44-5)

• 1. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 2. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
• 3. Emerging investigator series: heterogeneous reactions of sulfur dioxide on mineral dust nanoparticles: from single component to mixed components?
  Tao Wang,Yangyang Liu,Yue Deng,Hongbo Fu,Jianmin Chen Environ. Sci.: Nano, 2018,5, 1821-1833
• 4. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526
• 5. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592

4-(BOC-Methylamino)phenylboronic acid, pinacol ester: An Overview of Its Synthesis, Applications, and Recent Research Advances

4-(BOC-Methylamino)phenylboronic acid, pinacol ester (CAS No. 916587-44-5) is a versatile compound with significant applications in the fields of organic synthesis and medicinal chemistry. This compound, also known as 4-(tert-Butyloxycarbonyl-methylamino)phenylboronic acid pinacol ester, is a valuable building block for the synthesis of complex molecules, particularly in the development of pharmaceuticals and materials science.

The structure of 4-(BOC-Methylamino)phenylboronic acid, pinacol ester features a boronic acid moiety attached to a phenyl ring, which is further substituted with a BOC-protected methylamino group. The presence of the boronic acid functionality makes this compound highly reactive in Suzuki-Miyaura coupling reactions, a widely used method for the formation of carbon-carbon bonds. This reactivity is crucial for the synthesis of biologically active compounds and functional materials.

Recent research has highlighted the importance of 4-(BOC-Methylamino)phenylboronic acid, pinacol ester in various synthetic pathways. For instance, a study published in the Journal of Organic Chemistry demonstrated its utility in the synthesis of novel antitumor agents. The BOC protection group ensures that the amino functionality remains stable during synthetic manipulations, allowing for precise control over the final product's structure and properties.

In addition to its role in pharmaceutical synthesis, 4-(BOC-Methylamino)phenylboronic acid, pinacol ester has found applications in materials science. Researchers at the University of California, Berkeley, have utilized this compound to develop advanced polymers with tunable properties. The boronic acid functionality can be used to introduce cross-linking sites or to facilitate post-polymerization modifications, enhancing the material's performance in various applications such as drug delivery systems and sensors.

The synthetic route to 4-(BOC-Methylamino)phenylboronic acid, pinacol ester typically involves several steps. First, 4-aminophenylboronic acid is protected with a BOC group to form 4-(BOC-amino)phenylboronic acid. This intermediate is then methylated to introduce the methylamino group. Finally, the boronic acid is converted to its pinacol ester form using diisopropylethylamine (DIPEA) and 2-isopropoxy-1,3-dimethylimidazolidin-2-one (IPD). Each step requires careful optimization to ensure high yields and purity.

The stability and reactivity of 4-(BOC-Methylamino)phenylboronic acid, pinacol ester make it an attractive choice for researchers working on complex molecular architectures. Its ability to participate in Suzuki-Miyaura couplings without deprotection makes it particularly useful in multistep syntheses where maintaining functional group compatibility is essential.

In conclusion, 4-(BOC-Methylamino)phenylboronic acid, pinacol ester (CAS No. 916587-44-5) is a multifunctional compound with broad applications in organic synthesis and materials science. Its unique combination of reactivity and stability has made it an indispensable tool for researchers aiming to develop novel compounds and materials with advanced properties. As research continues to advance, it is likely that new applications for this compound will be discovered, further expanding its utility in both academic and industrial settings.

• 1218791-29-7(4-(N-BOC-N-phenylamino)phenylboronic acid, pinacol ester)
• 363186-06-5(Benzyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate)
• 330793-01-6(4-(Boc-amino)benzeneboronic acid pinacol ester)
• 330793-09-4(tert-Butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate)
• 1073371-71-7(4-(N-Boc-phenylaminomethyl)phenylboronic Acid Pinacol Ester)
• 1256360-04-9(4-(Boc-Amino)-2-methylphenylboronic Acid Pinacol Ester)
• 1346253-82-4(3-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-1,3-oxazolidin-2-one)
• 159624-15-4(Tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate)
• 817618-57-8(tert-butyl N-methyl-N-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate)
• 1312611-41-8(tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ylcarbamate)