2-Naphthaleneboronic acid
Synonym(s):2-Naphthaleneboronic acid
- CAS NO.:32316-92-0
- Empirical Formula: C10H9BO2
- Molecular Weight: 171.99
- MDL number: MFCD00236051
- EINECS: 628-070-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-18 17:01:59
What is 2-Naphthaleneboronic acid?
Chemical properties
yellow crystal powde
The Uses of 2-Naphthaleneboronic acid
suzuki reaction
The Uses of 2-Naphthaleneboronic acid
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).
Properties of 2-Naphthaleneboronic acid
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 |
form | Crystalline Powder and/or Chunks |
pka | 8.53±0.30(Predicted) |
color | White to off-white |
BRN | 2936449 |
CAS DataBase Reference | 32316-92-0(CAS DataBase Reference) |
Safety information for 2-Naphthaleneboronic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2-Naphthaleneboronic acid
InChIKey | KPTRDYONBVUWPD-UHFFFAOYSA-N |
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