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HomeProduct name listPHENYL-D5-BORONIC ACID

PHENYL-D5-BORONIC ACID

Synonym(s):(Pentadeuterophenyl)boronic acid

PHENYL-D5-BORONIC ACID Structural

What is PHENYL-D5-BORONIC ACID?

The Uses of PHENYL-D5-BORONIC ACID

Phenylboronic Acid-d5 is the isotope labelled analog of Phenylboronic Acid; 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%.

Properties of PHENYL-D5-BORONIC ACID

Melting point: 217-220 °C(lit.)
solubility  Chloroform (Slightly), DMSO
color  White
Stability: Hygroscopic
InChI InChI=1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H
CAS DataBase Reference 215527-70-1

Safety information for PHENYL-D5-BORONIC ACID

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P321:Specific treatment (see … on this label).

Computed Descriptors for PHENYL-D5-BORONIC ACID

InChIKey HXITXNWTGFUOAU-RALIUCGRSA-N
SMILES B(C1C([H])=C([H])C([H])=C([H])C=1[H])(O)O

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