2-Tolylboronic acid Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

ED7777777

HazardClass 

IRRITANT

HS Code 

29163990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Tolylboronic acid Chemical Properties,Usage,Production

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.