3,5-Dimethoxyphenylboronic acid

Bezeichnung:3,5-Dimethoxyphenylboronic acid

CAS-Nr192182-54-0

Englisch Name:3,5-Dimethoxyphenylboronic acid

CBNumberCB6716893

SummenformelC8H11BO4

Molgewicht181.98

MOL-Datei192182-54-0.mol

3,5-Dimethoxyphenylboronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	202-207 °C
Siedepunkt	371.6±52.0 °C(Predicted)
Dichte	1.19±0.1 g/cm3(Predicted)
Flammpunkt	81℃
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Soluble in methanol.
pka	7.67±0.10(Predicted)
Aggregatzustand	powder to crystal
Farbe	White to Light yellow to Light orange
InChI	1S/C8H11BO4/c1-12-7-3-6(9(10)11)4-8(5-7)13-2/h3-5,10-11H,1-2H3
InChIKey	XUIURRYWQBBCCK-UHFFFAOYSA-N
SMILES	COc1cc(OC)cc(c1)B(O)O
CAS Datenbank	192182-54-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36/37/39
WGK Germany	3
Hazard Note	Irritant/Keep Cold
HazardClass	IRRITANT, KEEP COLD
HS Code	29163990
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

3,5-Dimethoxyphenylboronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Gray to white solid
Verwenden
Reactant for:
- Palladium-catalyzed coupling reactions
- Preparation of benzopyranone derivatives as positive GABAA receptor modulators
- Preparation of aryl alkenes via three-component coupling catalyzed by palladium
- Suzuki-Miyaura coupling
- Rhodium catalyzed cyanation with N-cyano-N-phenyl-p-methylbenzenesulfonamide
- Preparation of bisphosphonate inhibitors of human farnesyl pyrophosphate synthase
Verwenden
suzuki reaction
Verwenden
3,5-Dimethoxyphenylboronic acid is a useful reagent for palladium-catalyst and Suzuki-Miyaura cross coupling reactions.
Synthese

5419-55-6

20469-65-2

192182-54-0

1. Synthesis of 3,5-dimethoxyphenylboronic acid: After cooling the flame-dried reaction vessel under argon protection, 3,5-dimethoxybromobenzene (3 g, 13.82 mmol) and anhydrous tetrahydrofuran (36 ml) were added. The mixture was stirred until a clarified solution was formed. Subsequently, the reaction mixture was cooled to -78 °C and maintained at this temperature for 15 minutes. n-Butyllithium (10.92 ml, 2.1 M hexane solution) was slowly added and the reaction mixture continued to be stirred at -78 °C for 30 minutes. Then, triisopropyl borate (5.2 g, 27.64 mmol) was added dropwise and the reaction was continuously stirred at -78°C for 2 hours. After completion of the reaction, it was slowly warmed up to room temperature and acidified with 2 M sulfuric acid solution to pH 2. The reaction mixture was extracted with ethyl acetate, the organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by recrystallization from petroleum ether to give 3,5-dimethoxyphenylboronic acid in 92% yield.
Einzelnachweise
[1] Patent: WO2008/118802, 2008, A1. Location in patent: Page/Page column 25-26

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