2-Naphthaleneboronic acid Chemical Properties

Melting point:

269-275 °C(lit.)

Boiling point:

381.9±25.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Slightly soluble in water

pka

8.53±0.30(Predicted)

form 

Crystalline Powder and/or Chunks

color 

White to off-white

BRN 

2936449

InChIKey

KPTRDYONBVUWPD-UHFFFAOYSA-N

CAS DataBase Reference

32316-92-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Naphthaleneboronic acid Usage And Synthesis

description

2-Naphthalene Boronic Acid is an organometallic iridium complex with applications in catalysis and Pharmaceutical manufacturing. It can be also used in the study of an enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones leading to chiral, tertiary trifluoromethyl alcohols.​

Uses

2-Naphthaleneboronic acid is a useful research chemical for organic synthesis and other chemical processes.

Solubility

Solubility in water: slightly soluble. Other solubilities: soluble in methanol

Application

It is used to study the enantioselective rhodium-catalyzed addition reaction of arylboronic acid and 2,2,2-trifluoroacetophenone to generate chiral tertiary trifluoromethanol. 
It can also be used to study the palladium-catalyzed addition reaction of arylboronic acid and nitrile to generate aryl ketones, and aromatic adverbial clauses: palladium-catalyzed addition of oxynitrile to benzofuran.

Chemical Properties

yellow crystal powde

Uses

suzuki reaction

Uses

Used in a study of an enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones leading to chiral, tertiary trifluoromethyl alcohols. Also employed in a study of a palladium-catalyzed addition of aryl boronic acids to nitriles providing aryl ketones and to aryloxy nitriles providing benzofurans.

Synthesis

To a two-neck 250mL round bottom flask, triisopropyl borate (3.30mL, 29.06mmol) and 3-bromoquinoline (3.00g, 14.49mmol) was dissolved in dry THF (100mL), then n-butyllithium (14.50mL of a 2M solution in hexane, 29.00mmol) was added dropwise via a dropping funnel over 1h under N2 at-78°C. After 2h, the acetone/dry ice bath was removed, and the reaction solution was allowed to warm to 0°C. The reaction was then quenched with a 2M HCl solution, and the pH value was adjusted to 7 with a solution of 2M NaHCO3. The resulting solution was extracted with ethyl acetate (EA) (3×100mL). The combined organic layers were dried with MgSO4 and evaporated to dryness. n-Hexane was then added to precipitated the product 2-Naphthaleneboronic acid as a white solid (80% yield).

2-Naphthaleneboronic acid(32316-92-0)Related Product Information

• Boric acid
• Citric acid
• Fluoroboric acid
• Zinc borate
• ALPHA-NAPHTHYLBORIC ACID,1-NAPHTHALENEBORONIC ACID,1-Naphthaleneboronic Acid (contains varying amounts of Anhydride)
• Ascoric Acid
• 3-(4-FLUOROPHENYL)AMINOCARBONYLPHENYLBORONIC ACID
• 4-FLUORO-3-(PHENYLCARBAMOYL)BENZENEBORONIC ACID
• 4-BROMO-1-FLUORO-2-NAPHTHALENEBORONIC ACID
• 6-Benzyloxy-2-naphthaleneboronic acid
• 6-HYDROXY-2-NAPHTHALENEBORONIC ACID
• 2-Naphthaleneboronic acid, pinacol ester ,98%,2-NAPHTHALENEBORONIC ACID, PINACOL ESTER
• 3-(PHENYLAMINOCARBONYL)-5-NITROPHENYLBORONIC ACID
• 6-T-BUTYLDIMETHYSILYLOXY-2-NAPHTHALENEBORONIC ACID
• 3-(4-CYANOPHENYL)AMINOCARBONYLPHENYLBORONIC ACID
• 6-ETHOXY-2-NAPHTHALENEBORONIC ACID
• (S)-2,2'-Dimethoxy-1,1'-binaphthyl-3,3'-diyldiboronic acid
• 3-(4-FLUOROPHENYL)AMINOCARBONYLPHENYLBORONIC ACID PINACOL ESTER