(2-METHOXY-1-NAPHTHYL)BORONIC ACID Chemical Properties

Melting point:

125-130°C

Boiling point:

425.2±47.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

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

pka

8.53±0.30(Predicted)

form 

solid

color 

White

InChI

InChI=1S/C11H11BO3/c1-15-10-7-6-8-4-2-3-5-9(8)11(10)12(13)14/h2-7,13-14H,1H3

InChIKey

NHVWTZOWDLOBBS-UHFFFAOYSA-N

SMILES

B(C1=C2C(C=CC=C2)=CC=C1OC)(O)O

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2931900090

(2-METHOXY-1-NAPHTHYL)BORONIC ACID Usage And Synthesis

Uses

Reactant for:

• Design of phosphorus C,P-ligands for environmentally benign cross-coupling reactions
• Sterically hindered Suzuki-Miyaura coupling
• Palladium-catalyzed cross-coupling reactions
• Deboronation homocoupling reactions
• Copper-catalyzed N-arylation of imidazoles
• Stereoselective preparation of biaryl compounds via palladium-catalyzed asymmetric Suzuki-Miyaura coupling

Synthesis

A tetrahydrofuran (THF, 50 mL) solution of 1-bromo-2-methoxynaphthalene (7.67 g, 32.36 mmol) was slowly added dropwise to a THF solution (15 mL) of magnesium shavings (0.905 g, 37.2 mmol) in a flame-dried reaction vessel protected by argon. The reaction mixture was stirred at room temperature for 2 hours, followed by warming to 50 °C and continued stirring for 1 hour. Upon completion of the reaction, the mixture was cooled to -78 °C and trimethyl borate (11.4 mL, 101.7 mmol) was slowly added. After remaining at -78 °C for 2 h, the reaction mixture was gradually warmed to room temperature and stirred overnight. After addition of water (40 mL), THF was removed by distillation under reduced pressure. the aqueous phase was extracted with dichloromethane, the organic phases were combined and dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated. The target product 2-methoxy-1-naphthylboronic acid was obtained by recrystallization from dichloromethane as a white powder in 80% yield. The structure of the product was confirmed by 1H NMR (400.14 MHz, CDCl3) and 13C{1H} NMR (75.47 MHz, [D6]DMSO).

References

[1] Journal of Organometallic Chemistry, 2013, vol. 743, p. 31 - 36
[2] Organic Process Research and Development, 2003, vol. 7, # 3, p. 379 - 384

(2-METHOXY-1-NAPHTHYL)BORONIC ACID(104116-17-8)Related Product Information

• Boric acid
• 2-ETHOXY-1-NAPHTHALENEBORONIC ACID
• (2-METHOXY-1-NAPHTHYL)BORONIC ACID
• 2-(2-Methoxynaphthalen-1-yl)-4,4,6-trimethyl-1,3,2-dioxaborinane
• 2-(2-METHOXY-1-NAPHTHYL)-5,5-DIMETHYL-1,3,2-DIOXABORINANE
• 2-(2-Benzyloxynaphthalen-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane
• 2-(2-Benzyloxynaphthalen-1-yl)-4,4,6-trimethyl-1,3,2-dioxaborinane