71597-85-8 Usage
Description
4-Hydroxyphenylboronic acid is an organic compound with the molecular formula C6H7BO3. It is a white crystalline solid that is soluble in water and has a hydroxyl group attached to a phenyl ring with a boronic acid functional group. 4-Hydroxyphenylboronic acid is known for its versatile reactivity and is widely used in various chemical reactions and applications.
Uses
Used in Chemical Synthesis:
4-Hydroxyphenylboronic acid is used as a reactant for Suzuki-Miyaura coupling and Stille coupling reactions, which are essential for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis. These reactions are crucial in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Cross-Coupling Reactions:
4-Hydroxyphenylboronic acid is employed in palladium-catalyzed aminocarbonylation and cross-coupling reactions, which are vital for the synthesis of various organic compounds, including pharmaceuticals and natural products.
Used in Catalyst Preparation:
4-Hydroxyphenylboronic acid is used in the preparation of bio-supported palladium nanoparticles as phosphine-free catalysts for Suzuki reactions in water. These catalysts are environmentally friendly and highly efficient for cross-coupling reactions.
Used in Polymer Synthesis:
4-Hydroxyphenylboronic acid is utilized in the synthesis of rod-like dendronized polymers containing G4 and G5 ester dendrons via the macromonomer approach by living ROMP (ring-opening metathesis polymerization). These dendronized polymers have potential applications in various fields, including drug delivery and sensing.
Used in Pharmaceutical Industry:
4-Hydroxyphenylboronic acid is used as a reactant for the preparation of PDK1 inhibitory activity compounds, which are known to inhibit cancer cell growth, survival, and tumorigenesis. It is also used in the synthesis of estrone-derived cyclopamine analogs, which act as Sonic Hedgehog signaling inhibitors for anti-cancer chemotherapeutics.
Used in Enzymatic Inhibitors:
4-Hydroxyphenylboronic acid is employed in the development of enzymatic inhibitors for the treatment of Gram-negative bacterial infections, which are a significant concern in the medical field due to their resistance to conventional antibiotics.
Used in Organic Synthesis:
4-Hydroxyphenylboronic acid is used to synthesize oligoarenes through Suzuki-Miyaura palladium-catalyzed cross-coupling reactions, which are essential for the development of novel materials and compounds with potential applications in various industries.
Synthesis Reference(s)
Tetrahedron Letters, 37, p. 6705, 1996 DOI: 10.1016/S0040-4039(96)01468-2
Check Digit Verification of cas no
The CAS Registry Mumber 71597-85-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,5,9 and 7 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 71597-85:
(7*7)+(6*1)+(5*5)+(4*9)+(3*7)+(2*8)+(1*5)=158
158 % 10 = 8
So 71597-85-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H7BO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8-10H
71597-85-8Relevant articles and documents
Method for preparing boric acid derivative (by machine translation)
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Paragraph 0040-0041, (2020/12/29)
The invention provides a preparation method of p-hydroxyphenylboronic acid. The method is characterized by comprising the following -0.1 mpa steps: at 0 - 10 °C vacuum conditions and temperature, heating the alkoxyl phenylboronic acid and acid first chloride compound in organic solvent, then heating the aqueous layer minutes every interval until 10 °C 15 the temperature is raised to, and then 30 - 100 °C carrying out 1 - 2h constant temperature reaction to obtain the intermediate pH. The aqueous layer 9-11 is further recrystallized by organic solvent 3-4 to obtain intermediate compound and second alkali adjusting system pH. 3rd. The p-hydroxyphenylboronic acid is obtained. The method has the advantages that the reaction temperature is relatively mild, the reaction time can be obviously shortened, the consumption of the catalyst is reduced, and the method has higher yield and purity. (by machine translation)
Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source
Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup
, p. 10966 - 10972 (2020/09/23)
In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.
Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water
Zernickel, Anna,Du, Weiyuan,Ghorpade, Seema A.,Sawant, Dinesh N.,Makki, Arwa A.,Sekar, Nagaiyan,Eppinger, J?rg
, p. 1842 - 1851 (2018/02/23)
A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
