3-Methoxycarbonylphenylboronic acid

Bezeichnung:3-Methoxycarbonylphenylboronic acid

CAS-Nr99769-19-4

Englisch Name:3-Methoxycarbonylphenylboronic acid

CBNumberCB6133384

SummenformelC8H9BO4

Molgewicht179.97

MOL-Datei99769-19-4.mol

3-Methoxycarbonylphenylboronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	205-208 °C(lit.)
Siedepunkt	359.9±44.0 °C(Predicted)
Dichte	1.25±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Aggregatzustand	Powder
pka	7.74±0.10(Predicted)
Farbe	White to off-white
Wasserlöslichkeit	Reacts with water.
InChI	InChI=1S/C8H9BO4/c1-13-8(10)6-3-2-4-7(5-6)9(11)12/h2-5,11-12H,1H3
InChIKey	ALTLCJHSJMGSLT-UHFFFAOYSA-N
SMILES	C(OC)(=O)C1=CC=CC(B(O)O)=C1
CAS Datenbank	99769-19-4(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	37/39-26-36
WGK Germany	3
HazardClass	IRRITANT
HS Code	29319090
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

3-Methoxycarbonylphenylboronic 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 to light yellow crystal powde
Verwenden
Reagent used for tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence, copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, one-pot ipso-nitration of arylboronic acids, copper-catalyzed nitration, cyclocondensation followed by palladium-phosphine-catalyzed Suzuki-Miyaura coupling. Reagent used in Preparation of biaryls via nickel-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acid6, chromenones and their bradykinin B1 antagonistic active, Pt nanoparticles at Photoactive metal-organic frameworks resulting in efficient hydrogen evolution via synergistic photoexcitation and electron injecti, salicylate-based thienylbenzoic acids as E. coli methionine aminopeptidase inhibitor.
Verwenden
3-Methoxycarbonylphenylboronic acid can be used in the preparation of substituted pyrazolylpyrimidinamine derivative for use as protein kinase inhibitors and suzuki reaction.
Synthese

67-56-1

25487-66-5

99769-19-4

In a 20 L reactor, 8.0 Kg of anhydrous methanol and 1.66 Kg (10 mol) of 3-carboxyphenylboronic acid were added and stirring was initiated. The reaction mixture was heated to 55°C and the temperature was maintained in the range of 55-65°C. 1.78Kg (15mol) of thionyl chloride was slowly added dropwise to the reaction kettle. After completion of the reaction, reflux was continued for 2-3 hours. The completion of the reaction was confirmed by TLC (unfolding agent: n-heptane/ethyl acetate = 2:1). The reaction solution was then cooled and subjected to reduced pressure distillation to remove the solvent. N-heptane was added and the mixture was cooled to -10 to 0°C and filtered with continuous stirring for 1 hour. The solid product was collected and dried at 80 °C until the absence of impurities was confirmed by HNMR (DMSO-d6, δ=3.16 ppm). The dried solid was stirred at room temperature and water was added, filtered and dried at room temperature to give 1.75 Kg of the final white solid product m-Carbomethoxyphenylboronic acid in 97.1% yield.
Einzelnachweise
[1] Patent: CN106188117, 2016, A. Location in patent: Paragraph 0015

3-Methoxycarbonylphenylboronic acid Upstream-Materialien And Downstream Produkte

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