4-(Hydroxymethyl)phenylboronic acid
(4-Hydroxymethylphenyl)boronic acid
CAS: 59016-93-2
Molecular Formula: C7H9BO3
4-(Hydroxymethyl)phenylboronic acid - Names and Identifiers
4-(Hydroxymethyl)phenylboronic acid - Physico-chemical Properties
| Molecular Formula | C7H9BO3 |
| Molar Mass | 151.96 |
| Density | 1.25±0.1 g/cm3(Predicted) |
| Melting Point | 251-256 °C (lit.) |
| Boling Point | 362.0±44.0 °C(Predicted) |
| Flash Point | 172.744°C |
| Water Solubility | 25 g/L |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White-like crystal |
| Color | White to slightly yellow |
| BRN | 2831413 |
| pKa | 8.53±0.10(Predicted) |
| PH | 4.5 (10g/l, H2O) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.567 |
| MDL | MFCD00792672 |
4-(Hydroxymethyl)phenylboronic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| HS Code | 29319090 |
| Hazard Class | IRRITANT |
4-(Hydroxymethyl)phenylboronic acid - Reference Information
| Introduction | 4-hydroxymethylphenylboronic acid is a kind of substituted Phenylboronic acid with superior performance, this Phenylboronic acid shows a more superior binding ability to sugars in neutral aqueous solutions. 4-hydroxymethylphenylboronic acid ligand has very low acid dissociation constant (pKa) and strong binding ability to cis-dihydroxy compounds, which can specifically enrich cis-dihydroxy compounds under neutral and acidic conditions, such as nucleosides and glycoproteins. In addition, 4-hydroxymethylphenylboronic acid has a high retention capacity, which is suitable for high throughput analysis of various complex biological samples, and it is a good solution to the current problems faced by boron affinity materials. |
| Use | 4-hydroxymethylphenylboronic acid is a boronic acid derivative. Boronic acid derivatives are widely used in organic synthesis for the formation of carbon-carbon bonds. In Suzuki coupling, aryl halides and aryl or vinyl borates or boronic acids are coupled using Pd(PPh3)4. |
| Application | due to the strong binding capacity and excellent water solubility of 4-hydroxymethylphenylboronic acid, this class of substituted Phenylboronic acids has even more superior ability to bind sugars in aqueous solution than the Wulff-type Phenylboronic acids. 4-hydroxymethylphenylboronic acid has been shown to outperform other classes of substituted boronic acids in carbohydrate recognition under neutral conditions and is widely used as an affinity ligand to recognize glycoproteins, such as TF-antibody and gp -120 in HI Virus. In addition, 4-hydroxymethylphenylboronic acid is also widely used as an enzyme inhibitor, such as an anti-vertebral body insect. The boronic acid of 4-hydroxymethylphenylboronic acid may well solve the problems mentioned above with respect to boron affinity materials. |
| Application example | 4-hydroxymethylphenylboronic acid can be used to prepare 4-amino-pyrimidino heterocyclic derivatives having the following structure, this class of compounds is a BTK inhibitor. BTK activates FcγR signaling through immune complexes in bone marrow cell function. In macrophages, BTK inhibition blocks Fc gamma RIII-induced inf-α, IL-1β, and IL-6 products, blocking BCR-dependent B- cell proliferation through NF-kB activation, this provides strong evidence for the treatment of BTK in autoimmune diseases, including rheumatoid arthritis and systemic erythema. In addition, BTK has been demonstrated to be a target for the treatment of lymphoma-related diseases. |
| preparation | The first step synthesis of 4-hydroxymethyl-benzeneboronic acid styrenyl ester methyl 4-bromomethylbenzoate 10.02G, cyano diboron 13.00G, potassium acetate 1.28G,[1,1 '-bis (diphenylphosphine) ferrocene] Palladium dichloride 0.095g was placed in a three-necked 100 vial and a vacuum was applied and nitrogen was charged. In a nitrogen atmosphere, 30 ml of dioxane was added and the mixture was reacted at 100 ° C. For 12 hours. After cooling to room temperature, 50 ml of ethyl acetate and 50 ml of water were added, the organic layer was separated, washed twice with water, once with brine, and dried over anhydrous magnesium sulfate. After filtration and concentration to remove the solvent, the residue was separated by column chromatography and eluted (EtOAc: Hexane = 1: 50,v/v) to obtain a white solid of 4-hydroxymethyl benzene boronate ester, the yield was 92%. Step 2 synthesis of 4-hydroxymethylphenylboronic acid weigh 1.12G of the product obtained in the first step and dissolve it into 30 ml of carbon tetrachloride, then add 0.81g of N-bromosuccinimide and 0.036g of azobisisobutyronitrile, after heating to reflux for 4H and cooling to room temperature, The reaction solution was washed twice with water, once with brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed under reduced pressure and the resulting crude product was dissolved in 50 ml of diethyl ether. The diethyl ether phase was extracted three times with 15% potassium hydroxide and the resulting aqueous phases were combined. In an ice bath, the pH of the aqueous phase is adjusted to 1 with hydrochloric acid under magnetic stirring, a white precipitate is precipitated, and the resulting white solid is collected and washed with an appropriate amount of chloroform, vacuum drying gave 0.45g of 4-hydroxymethylphenylboronic acid as a white solid in 62% yield. |
Last Update：2024-04-10 22:29:15
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