| Identification | Back Directory | [Name]
PHENYL-D5-BORONIC ACID | [CAS]
215527-70-1 | [Synonyms]
PHENYL-D5-BORONIC ACID
phenyl-d5-boronicacid98atom%d
(Perdeuterophenyl)boronic acid
9-bromo-10-(phenyl-d5)anthracene
B-(Phenyl-2,3,4,5,6-d5)boronic acid
Boronic acid,B-(phenyl-2,3,4,5,6-d5)-
2,3,4,5,6-Pentadeuteriumbenzeneboronic Acid | [Molecular Formula]
C6H2BD5O2 | [MDL Number]
MFCD02093711 | [MOL File]
215527-70-1.mol | [Molecular Weight]
126.96 |
| Chemical Properties | Back Directory | [Melting point ]
217-220 °C(lit.)
| [solubility ]
Chloroform (Slightly), DMSO | [form ]
solid | [color ]
White | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H | [InChIKey]
HXITXNWTGFUOAU-RALIUCGRSA-N | [SMILES]
B(C1C([H])=C([H])C([H])=C([H])C=1[H])(O)O | [CAS DataBase Reference]
215527-70-1 | [CAS Number Unlabeled]
215527-70-1 |
| Hazard Information | Back Directory | [Uses]
Phenylboronic Acid-d5 is the isotope labelled analog of Phenylboronic Acid (P319590); a compound used in the organic synthesis of various pharmaceutical goods. | [Synthesis]
A dry three-neck flask equipped with a rubber septum, an addition funnel equipped with a rubber septum, and a condenser was charged under nitrogen with magnesium turnings. To the addition funnel was added D5-bromobenzene (6.5 mL, 62 mmol) (Aldrich) dissolved in a 1:1 mixture of THF/toluene (31 mL). Grignard reagent formation was observed after about after about 1 mL of the contents of the addition funnel had been added to the magnesium turnings. The remaining bromobenzene solution was added dropwise over a period of about 1 h. After the addition was complete the reaction mixture was heated at 70° C. for 1 h. The reaction mixture was cooled to room temperature and added via a canulating needled to an addition funnel on a second three-neck flask containing a solution of triethylborate (B(OEt)3) (10.5 mL, 62 mmol) in toluene (10 mL) maintained at 0° C. The solution of the freshly prepared Grignard reagent was then added dropwise to the solution of triethylborate over a period of 1 h. The cooling bath was then removed and the reaction mixture was allowed to stir at room temperature for 15 h. The reaction mixture was quenched with 10% H2SO4 (30 mL) and stirred at room temperature for 1 h. The layers were separated and the organic layer was dried over Na2SO4. After removal of the solvent, addition of hexane precipitated the product as an off-white solid, which was collected by filtration and dried to afford Phenyl-d5-boronic acid. Its yield: 3.50 g, 45%. |
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