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365564-10-9

365564-10-9 Structure

365564-10-9 Structure
IdentificationBack Directory
[Name]

3,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER
[CAS]

365564-10-9
[Synonyms]

4-DiMethoxyloxyphenyl)-4
2-(3,4-Dimethoxyphenyl)-4,4,5,5-tetramethyl-
3,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER
3,4-Dimethoxybenzeneboronic acid, pinacol ester
3,4-Dimethoxybenzeneboronic acid, pinacol ester 97%
3,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER-YL) METHANAMINE
2-(3,4-DIMETHOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
1,3,2-Dioxaborolane, 2-(3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-
2-(3,4-DIMETHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
1,2-Dimethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
[Molecular Formula]

C14H21BO4
[MDL Number]

MFCD05863909
[MOL File]

365564-10-9.mol
[Molecular Weight]

264.13
Chemical PropertiesBack Directory
[Melting point ]

86-87°C
[Boiling point ]

352.5±32.0 °C(Predicted)
[density ]

1.05±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[form ]

powder to crystal
[color ]

White to Almost white
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H312+H332-H315-H319-H335
[Precautionary statements ]

P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

20/21/22-36/37/38-36
[Safety Statements ]

36/37/39-26
[WGK Germany ]

3
[HS Code ]

2931900090
Spectrum DetailBack Directory
[Spectrum Detail]

3,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER(365564-10-9)1HNMR
Hazard InformationBack Directory
[Synthesis]

1,2-Dimethoxybenzene

91-16-7

Bis(pinacolato)diboron

73183-34-3

3,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER

365564-10-9

The reaction of 1,2-dimethoxybenzene (69.9 mg, 0.506 mmol, 1.0 eq.) and bis(pinacolato)diboron (124 mg, 0.486 mmol, 0.96 eq.) was catalyzed by 2,2'-bipyridine (1.7 mg, 11 μmol, 2.2 mol%) and [IrCl(cod)]2 (2.3 mg, 3.4 μmol , 0.68 mol%) were catalyzed by a stirring reaction in heptane (2.5 mL) at 95 °C for 24 hours. After completion of the reaction, the reaction was cooled to room temperature and the reaction mixture was concentrated under reduced pressure and used directly in the next step of the reaction. Subsequently, S-(4-tolyl)-4-toluene thiosulfonate (2a) (69.1 mg, 0.248 mmol, 1.0 equiv), copper sulfate (2.0 mg, 13 μmol, 5.0 mol%), cesium fluoride (80.6 mg, 0.530 mmol, 2.1 equiv), and TMEDA (1.9 mg, 0.16 μmol, 6.6 mol%) were added to the above crude product, dissolved in methanol (2.5 mL) and stirred at 50 °C for 24 hours. After completion of the reaction, it was cooled to room temperature, filtered through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure. The residue was dissolved with ethyl acetate (20 mL), washed sequentially with saturated aqueous sodium bicarbonate (20 mL x 2) and brine (20 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and purified by preparative TLC (n-hexane/ethyl acetate=10/1) to afford 3,4-dimethoxyphenyl 4-methylphenyl sulfide (3t) (39.7 mg, 61.4%) as a light yellow oil.

[References]

[1] Patent: WO2013/175415, 2013, A1. Location in patent: Page/Page column 46
[2] Journal of the American Chemical Society, 2015, vol. 137, # 7, p. 2665 - 2673
[3] Journal of the American Chemical Society, 2014, vol. 136, # 18, p. 6566 - 6569
[4] Journal of the American Chemical Society, 2002, vol. 124, # 3, p. 390 - 391
[5] Journal of the American Chemical Society, 2015, vol. 137, # 15, p. 5193 - 5198
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