4-Benzyloxybenzeneboronic acid

Bezeichnung:4-Benzyloxybenzeneboronic acid

CAS-Nr146631-00-7

Englisch Name:4-Benzyloxybenzeneboronic acid

CBNumberCB4470742

SummenformelC13H13BO3

Molgewicht228.05

MOL-Datei146631-00-7.mol

4-Benzyloxybenzeneboronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	193-199 °C
Siedepunkt	418.9±47.0 °C(Predicted)
Dichte	1.20±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Chloroform, DMSO, Methanol
Aggregatzustand	solid
pka	8.70±0.16(Predicted)
Farbe	White to Off-White
InChI	1S/C13H13BO3/c15-14(16)12-6-8-13(9-7-12)17-10-11-4-2-1-3-5-11/h1-9,15-16H,10H2
InChIKey	DMJHEIDWSIAXCS-UHFFFAOYSA-N
SMILES	OB(O)c1ccc(OCc2ccccc2)cc1
CAS Datenbank	146631-00-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,C
R-Sätze:	36/37/38
S-Sätze:	37/39-26-36-24/25
WGK Germany	3
Hazard Note	Corrosive
HazardClass	IRRITANT
HS Code	29310095
Speicherklasse	13 - Non Combustible Solids

Gefahreninformationscode (GHS)

4-Benzyloxybenzeneboronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
white crystalline powder
Verwenden
4-Benzyloxybenzeneboronic Acid is a reagent in the synthesis of arylalkenylpropargylamines as neuroprotective and potent selective monoamine oxidase B inhibitors. Also used to prepare pyridone alkaloids used as antiproliferative agents.
Verwenden
It is used as electronic intermediate. It is also utilized in HPLC and NMR spectroscopy.
Verwenden
suzuki reaction
Allgemeine Beschreibung
May contain varying amounts of anhydride
Synthese

6793-92-6

146631-00-7

First, 5.07 g of magnesium shavings and 80 mL of anhydrous tetrahydrofuran were added to a 500 mL three-necked flask that had been displaced by argon. A small amount of iodine crystals was added to activate the magnesium. Subsequently, 100 mL of anhydrous tetrahydrofuran solution containing 45.7 g of 4-bromo-1-benzyloxybenzene (obtained from synthesis step 10-a) was slowly added dropwise to the above mixture under stirring conditions. After the dropwise addition was completed, the reaction mixture was heated and refluxed and stirred for 30 minutes and subsequently cooled to -40°C. At this temperature, 60 mL of anhydrous tetrahydrofuran solution containing 21.66 g of trimethylborate was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was allowed to gradually warm up to room temperature and reflux stirring was continued for 30 minutes. After that, the reaction mixture was cooled to 0 °C again, 200 mL of 10% aqueous sulfuric acid solution was added and stirred for 1 hour. Upon completion of the reaction, toluene was added to the mixture to extract the organic layer. The organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the crude product obtained was recrystallized from toluene to give 36.5 g (yield: 92.1%) of the title compound 4-benzyloxyphenylboronic acid.
Einzelnachweise
[1] Patent: US6388146, 2002, B1. Location in patent: Page column 35
[2] Angewandte Chemie - International Edition, 2004, vol. 43, # 39, p. 5235 - 5238
[3] Organic and Biomolecular Chemistry, 2010, vol. 8, # 21, p. 4831 - 4833
[4] European Journal of Organic Chemistry, 2012, # 7, p. 1448 - 1454
[5] Journal of the American Chemical Society, 2011, vol. 133, # 39, p. 15674 - 15685

4-Benzyloxybenzeneboronic acid Upstream-Materialien And Downstream Produkte

4-Benzyloxybenzeneboronic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

146631-00-7, 4-Benzyloxybenzeneboronic acid Verwandte Suche:

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