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| | 3-Chlorophenylboronic acid Basic information |
| | 3-Chlorophenylboronic acid Chemical Properties |
| Melting point | 185-189 °C(lit.) | | Boiling point | 311.4±44.0 °C(Predicted) | | density | 1.32±0.1 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | soluble in Methanol | | pka | 7.55±0.10(Predicted) | | form | Crystalline Powder or Needles | | color | White to light yellow-green | | Water Solubility | Slightly soluble in water. soluble in ether, tetrahydrofuran,, dimethyl sulfoxide, dimethyl formamide, methanol. | | BRN | 2936343 | | InChI | InChI=1S/C6H6BClO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H | | InChIKey | SDEAGACSNFSZCU-UHFFFAOYSA-N | | SMILES | B(C1=CC=CC(Cl)=C1)(O)O | | CAS DataBase Reference | 63503-60-6(CAS DataBase Reference) |
| | 3-Chlorophenylboronic acid Usage And Synthesis |
| Chemical Properties | white to light yellow-green crystalline powder | | Uses | suzuki reaction | | Uses | Reactant involved in:
- 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamides
- Suzuki-Miyaura reactions with dibromotrifluoromethylbenzene
- Cross-coupling reactions with diazoesters or potassium cyanate
- Synthesis of biarylketones and phthalides
- Synthesis of inhibitors including PDE4 inhibitors among others
| | Uses |
3-Chlorophenylboronic acid is employed as a reactant involved in 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamides, Suzuki-Miyaura reactions with dibromotrifluoromethylbenzene, cross-coupling reactions with diazoesters3 or potassium cyanate. It is involved in the synthesis of biarylketones and phthalides and synthesis of inhibitors including PDE4 inhibitors6 among others.
| | Synthesis | Using m-dichlorobenzene as the starting material, iodine particles and 1,2-dibromoethane as the initiator reacts with magnesium in an organic solvent to prepare 3-chlorophenyl magnesium chloride. Then, the trimethyl borate is reacted with an organic solvent to prepare 3-chlorophenyl borate dimethyl ester. Finally, the product 3-chlorophenylboronic acid is obtained through hydrolysis, extraction, and crystallization. | | Solubility in organics | 3-Chlorophenylboronic acid can be dissolved in organic solvents such as N, N-dimethylformamide, ethyl acetate, and dichloromethane. In addition, it also has specific solubility in low-polarity and non-polar organic solvents, but 3-chlorophenylboronic acid has poor solubility in water. | | References | [1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 590 - 603
[2] Organic Letters, 2005, vol. 7, # 21, p. 4757 - 4759
[3] Tetrahedron, 2007, vol. 63, # 35, p. 8529 - 8536 |
| | 3-Chlorophenylboronic acid Preparation Products And Raw materials |
| Raw materials | 3-BROMOCHLOROBENZENE-->Trimethyl borate-->n-Butyllithium-->Tetrahydrofuran-->Hexane | | Preparation Products | 3-CHLOROPHENYLBORONIC ACID, PINACOL ESTER-->Cyclohexanone, 3-(3-chlorophenyl)-, (3R)--->6-(3-Chlorophenyl)picolinaldehyde-->RARECHEM AL BF 1350-->[1,1'-Biphenyl]-3-carboxylic acid, 3'-chloro-, methyl ester-->3-(3-CHLOROPHENYL)CYCLOPENTANONE-->(S)-2-((tert-butoxycarbonyl)amino)-3-(3'-chloro-[1,1'-biphenyl]-4-yl)propanoicacid-->4-BROMO-3'-CHLOROBENZOPHENONE-->4-(3-chlorophenyl)butanoicacid-->3,3',4,5-TETRACHLOROBIPHENYL-->2-(3-CHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXALDEHYDE 97 |
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