2-Tolylboronic acid
Synonym(s):2-Methylphenylboronic acid;2-Tolueneboronic acid;(2-Tolyl)boronic acid;o-Boronotoluene;o-Methylphenylboronic acid
- CAS NO.:16419-60-6
- Empirical Formula: C7H9BO2
- Molecular Weight: 135.96
- MDL number: MFCD00093526
- EINECS: 605-351-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-07-11 11:22:35
What is 2-Tolylboronic acid?
Physical properties
beige crystalline powder
The Uses of 2-Tolylboronic acid
suzuki reaction
The Uses of 2-Tolylboronic acid
2-Methylbenzeneboronic acid is a reagent used for Pd-catalyzed arylation using Suzuki-Miyaura cross-coupling in water, Ruthenium catalyzed direct arylation reactions, Ligand-free copper-catalyzed coupling reactions, Rhodium-catalyzed asymmetric 1,4-addition reactions. Reagent used in Preparation of chiral monophosphorus ligands in asymmetric Suzuki-Miyaura coupling reaction, Human farnesyl pyrophosphate synthase inhibitors as antitumor agents for multiple myeloma cells
Synthesis
Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol %), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol %) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 °C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3×10 mL). The aqueous layer was then cooled to 0 °C (ice bath) and acidified to pH ≤1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3×10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid named 2-Tolylboronic acid.
Properties of 2-Tolylboronic acid
Melting point: | 162-164 °C(lit.) |
Boiling point: | 283.4±33.0 °C(Predicted) |
Density | 1.10±0.1 g/cm3(Predicted) |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
form | Crystalline Powder |
pka | 8.61±0.58(Predicted) |
color | Beige |
Water Solubility | Slightly soluble in water. |
BRN | 2935796 |
InChI | InChI=1S/C7H9BO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5,9-10H,1H3 |
CAS DataBase Reference | 16419-60-6(CAS DataBase Reference) |
Safety information for 2-Tolylboronic 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-Tolylboronic acid
InChIKey | NSJVYHOPHZMZPN-UHFFFAOYSA-N |
SMILES | B(C1=CC=CC=C1C)(O)O |
Abamectin manufacturer
REDDY N REDDY PHARMACEUTICALS
ARRKEM LIFE SCIENCES PRIVATE LIMITED
Rivashaa Agrotech Biopharma Pvt. Ltd.
Denisco Chemicals Pvt Ltd
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