3,4-Dimethoxyphenylboronic acid

Bezeichnung:3,4-Dimethoxyphenylboronic acid

CAS-Nr122775-35-3

Englisch Name:3,4-Dimethoxyphenylboronic acid

CBNumberCB7334366

SummenformelC8H11BO4

Molgewicht181.98

MOL-Datei122775-35-3.mol

3,4-Dimethoxyphenylboronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	245-250 °C (lit.)
Siedepunkt	336.7±52.0 °C(Predicted)
Dichte	1.19±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Aggregatzustand	Powder and Granules
pka	8.48±0.10(Predicted)
Farbe	White to light beige
Wasserlöslichkeit	25 g/L
BRN	5334877
InChI	InChI=1S/C8H11BO4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5,10-11H,1-2H3
InChIKey	RCVDPBFUMYUKPB-UHFFFAOYSA-N
SMILES	B(C1=CC=C(OC)C(OC)=C1)(O)O
CAS Datenbank	122775-35-3(CAS DataBase Reference)

Sicherheit

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

Gefahreninformationscode (GHS)

3,4-Dimethoxyphenylboronic 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.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Chemische Eigenschaften
white to light beige powder and granules
Verwenden
3,4-Dimethoxyphenylboronic acid can be used:
- As a substrate in the cross-coupling reaction with 5,7-dichloropyrido[4,3-d]pyrimidine catalyzed by palladium.
- As a starting material for the synthesis of buflavine 1, a natural alkaloid.
- In one of the key synthetic steps for the preparation of lipidated malarial glycosylphosphatidylinositols (GPI) disaccharide.
- To prepare 3,3″,4,4″-tetramethoxy-1,1′:4′,1″-terphenyl by reacting with 1,4-dibromobenzene using Pd catalyst.
Verwenden
suzuki reaction
Synthese

6315-89-5

122775-35-3

GENERAL PROCEDURE: 3,4-Dimethoxyaniline (0.5 mmol, 1.0 eq.) was dissolved in methanol (1.0 mL), hydrochloric acid (0.5 mL, 1.5 mmol, 3.0 eq.) was slowly added, followed by water (0.5 mL). The reaction mixture was stirred for 2 min, then sodium nitrite solution (0.25 mL, prepared by dissolving 35 mg NaNO2 in 0.25 mL of water) was added. The reaction mixture was stirred at 0-5 °C for 30 min, followed by the addition of methanol (1.0 mL) and hydrochloric acid (135 mg, 1.5 mmol, 3.0 equiv). Stirring was continued for 60 min. Upon completion of the reaction, it was diluted with water (10 mL) and extracted with dichloromethane (50 mL, 3 times). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3,4-dimethoxyphenylboronic acid.
Einzelnachweise
[1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584

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