[1,1-Biphenyl]-3-ylboronic acid
Biphenyl-3-boronic acid
CAS: 5122-95-2
Molecular Formula: C12H11BO2
[1,1-Biphenyl]-3-ylboronic acid - Names and Identifiers
| Name | Biphenyl-3-boronic acid |
| Synonyms | Biphenyl-3-boronica 3- biphenylboric acid 3-BIPHENYLBORONIC ACID 3-Biphenylboronic acid 3-Biphenyl boronic acid Biphenyl-3-boronic acid biphenyl-3-ylboronic acid 3-Phenylbenzeneboronic acid (1,1-Biphenyl-3-yl)boronic acid [1,1-Biphenyl]-3-ylboronic acid 2-phenylphenyl hydrogen boronate [1,1'-Biphenyl]-3-ylboronic acid [1,1'-BIPHENYL]-3-YLBORONIC ACID 3-Biphenylboronic Acid (contains varying amounts of Anhydride) |
| CAS | 5122-95-2 |
| EINECS | 671-848-2 |
| InChI | InChI=1/C12H11BO2/c14-13(15)12-8-4-7-11(9-12)10-5-2-1-3-6-10/h1-9,14-15H |
| InChIKey | GOXICVKOZJFRMB-UHFFFAOYSA-N |
[1,1-Biphenyl]-3-ylboronic acid - Physico-chemical Properties
| Molecular Formula | C12H11BO2 |
| Molar Mass | 198.03 |
| Density | 1.18±0.1 g/cm3(Predicted) |
| Melting Point | 193-198 °C (lit.) |
| Boling Point | 411.0±38.0 °C(Predicted) |
| Flash Point | 202.3°C |
| Water Solubility | Insoluble in water. |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Vapor Presure | 1.72E-07mmHg at 25°C |
| Appearance | Crystalline powder |
| Color | White to Off-White |
| BRN | 2836311 |
| pKa | 8.30±0.10(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.61 |
| MDL | MFCD01318102 |
[1,1-Biphenyl]-3-ylboronic acid - Risk and Safety
| 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. |
| WGK Germany | 3 |
| HS Code | 29163990 |
| Hazard Note | Corrosive |
[1,1-Biphenyl]-3-ylboronic acid - Reference Information
| Application | 3-biphenylboronic acid is an organic intermediate, often used in metal coupling reactions. 3-biphenylboronic acid can be prepared from 1, 3-dibromobenzene and phenylboronic acid through a two-step reaction. |
| preparation | 1. preparation of compound 5-1: 1,3-dibromobenzene (58g, 246 mmol), phenylboronic acid (20g, 164 mmol), Pd(PPh3)4(5.6g, 4.8 mmol) and Na2CO3(52g, after 492 mmol) is dissolved in the mixed solvent toluene (120 ml)/EtOH(40 ml), the reaction mixture is stirred at 90°C for 3 hours. Then, the reaction was terminated by slowly adding distilled water, and the reaction mixture was extracted with EA. The resulting organic layer was dried with anhydrous MgSO4 to remove residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to obtain compound 5-1(26g, 70%). 2. Preparation of Compound 5-2 After dissolving compound 5-1(26g, 111 mmol) in THF(500 mL), the reaction mixture was cooled to -78°C. After 10 minutes, slowly add n-BuLi(66.6 ml, 166.5 mmol, 2.5M hexane solution) and stir the reaction mixture for 1 hour. Then, B(OMe)3(24.7 ml, 222 mmol) was slowly added and the reaction mixture was stirred for 24 hours. After the termination of the reaction, 1M HCl was added and the reaction mixture was extracted with EA. The resulting organic layer was dried with anhydrous MgSO4 to remove residual moisture, distilled under reduced pressure to remove solvent, and recrystallized with MC/hexane to give compound 5-2, 3-biphenylboronic acid (14.3g, 65%). |
Last Update：2024-04-10 22:29:15
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