Production Method 1

14047-29-1

850568-54-6

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Dichloromethane ,  Water ;  -78 °C; 24 h, rt; rt → -78 °C; -78 °C → rt

Reference

Abc amino acids: Design, synthesis, and properties of new photoelastic amino acids

Standaert, Robert F.; Park, Seung Bum, Journal of Organic Chemistry, 2006, 71(21), 7952-7966

Production Method 2

850568-72-8

850568-54-6

Reaction Conditions

1.1 Reagents: Ammonium acetate ,  Sodium periodate Solvents: Acetone ,  Water ;  overnight, rt

Reference

A New Approach to Non-Coordinating Anions: Lewis Acid Enhancement of Porphyrin Metal Centers in a Zwitterionic Metal-Organic Framework

Johnson, Jacob A.; Petersen, Brenna M.; Kormos, Attila; Echeverria, Elena; Chen, Yu-Sheng; et al, Journal of the American Chemical Society, 2016, 138(32), 10293-10298

(4-(tert-Butoxycarbonyl)phenyl)boronic acid Raw materials

• 4-(dihydroxyboranyl)benzoic acid
• Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

(4-(tert-Butoxycarbonyl)phenyl)boronic acid Preparation Products

• (4-(tert-Butoxycarbonyl)phenyl)boronic acid (850568-54-6)

• 1. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466
• 2. Excellent lithium ion storage property of porous MnCo2O4 nanorods?
  Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen Fang RSC Adv., 2016,6, 23074-23084
• 3. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832
• 4. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 5. 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

• 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
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to (4-(tert-Butoxycarbonyl)phenyl)boronic Acid (CAS No 850568-54-6)

The compound (4-(tert-Butoxycarbonyl)phenyl)boronic acid, with the CAS registry number 850568-54-6, is a significant intermediate in organic synthesis. This compound is widely utilized in the field of medicinal chemistry and materials science due to its unique properties and versatility. The structure of this compound consists of a phenyl ring substituted with a tert-butoxycarbonyl group and a boronic acid moiety, which makes it highly reactive and suitable for various cross-coupling reactions.

Recent advancements in organoboron chemistry have highlighted the importance of (4-(tert-Butoxycarbonyl)phenyl)boronic acid in the synthesis of biologically active molecules. The boronic acid group is particularly valuable in Suzuki-Miyaura coupling reactions, where it serves as a key component for forming carbon-carbon bonds. This reactivity has been extensively explored in the development of novel pharmaceutical agents, including anti-cancer drugs and neuroprotective compounds.

One of the most notable applications of this compound is its role in the construction of complex aromatic systems. By leveraging its reactivity, researchers have successfully synthesized a range of heterocyclic compounds that exhibit potent biological activities. For instance, studies published in the Journal of Medicinal Chemistry have demonstrated its utility in the creation of kinase inhibitors, which are critical in targeted cancer therapy.

In addition to its role in drug discovery, (4-(tert-Butoxycarbonyl)phenyl)boronic acid has also found applications in materials science. Its ability to participate in cross-coupling reactions has made it a valuable precursor for the synthesis of advanced materials, such as organic semiconductors and functional polymers. These materials are pivotal in the development of next-generation electronic devices and sensors.

The synthesis of (4-(tert-Butoxycarbonyl)phenyl)boronic acid typically involves multi-step processes that require precise control over reaction conditions. Recent research has focused on optimizing these synthetic routes to enhance yield and purity. For example, methodologies involving transition metal catalysts have been employed to streamline the production process, making it more efficient and scalable for industrial applications.

Furthermore, the stability and storage conditions of this compound are critical considerations for its practical use. Studies have shown that (4-(tert-Butoxycarbonyl)phenyl)boronic acid is stable under standard laboratory conditions but requires protection from moisture and oxygen to prevent degradation. These insights have informed best practices for handling and storing this compound in research and industrial settings.

Looking ahead, the continued exploration of (4-(tert-Butoxycarbonyl)phenyl)boronic acid's potential is expected to drive further innovations in organic synthesis. Its role as a versatile building block positions it as an essential tool for researchers across various disciplines, from medicinal chemistry to materials science.

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