2-Tolylboronic acid Chemical Properties

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)

pka

8.61±0.58(Predicted)

form 

Crystalline Powder

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

InChIKey

NSJVYHOPHZMZPN-UHFFFAOYSA-N

SMILES

B(C1=CC=CC=C1C)(O)O

CAS DataBase Reference

16419-60-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

ED7777777

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:2-Tolylboronic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Tolylboronic acid Usage And Synthesis

Description

2-Methylphenylboronic acid is an important organic boronic acid compound, which is widely used in Suzuki cross-coupling reaction and has important application value in the fields of organic synthesis and medicine and chemical industry.

Physical properties

beige crystalline powder

Uses

suzuki reaction

Uses

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.

2-Tolylboronic acid(16419-60-6)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• Citric acid
• Folic acid
• p-Toluenesulfonic acid
• 3,5-Dimethylphenylboronic acid
• 3-Nitrophenylboronic acid
• 2-Chloro-5-chloromethylpyridine
• 5-Amino-2-methylpyridine
• Phenylboronic acid
• Methylboronic acid
• 2,5-Dimethylpyridine
• Dichloromethylphenylsilane
• Methyltriphenylphosphonium bromide
• o-Toluoyl chloride
• Ascoric Acid
• O-TOLYLHYDRAZINE HYDROCHLORIDE
• Methyl 2-methoxybenzoate
• o-Toluic acid