3-Tolylboronic acid Chemical Properties

Melting point:

160-162 °C(lit.)

Boiling point:

290.4±33.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Slightly soluble in water

pka

8.63±0.10(Predicted)

form 

Powder and Chunks

color 

Beige

BRN 

2935968

InChI

InChI=1S/C7H9BO2/c1-6-3-2-4-7(5-6)8(9)10/h2-5,9-10H,1H3

InChIKey

BJQCPCFFYBKRLM-UHFFFAOYSA-N

SMILES

B(C1=CC=CC(C)=C1)(O)O

CAS DataBase Reference

17933-03-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

ED7788888

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:3-Methylphenylboronic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Tolylboronic acid Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

3-methylphenylboronic acid can be used in Suzuki coupling reactions and is studied in the field of chemical engineering.

Application

3-Tolylboronic acid is an impurity of Eltrombopag, Eltrombopag is used to treat low blood platelet counts in adults with chronic immune (idiopathic) thrombocytopenia (ITP), when certain other medicines, or surgery to remove the spleen, have not worked well enough.

Synthesis

The general procedure for the synthesis of 3-methylphenylboronic acid from trimethyl borate and 3-bromomethylbenzene is as follows: 0.10 mol (0.1 eq.) of 3-bromomethylbenzene, 1.1 mol (1.1 eq.) of magnesium scraps, a few iodine crystals, and 800 mL of tetrahydrofuran (THF) were added to a reaction flask, stirred and heated to reflux. When the Grignard reaction was initiated, 0.90 mol (0.9 eq.) of 3-bromomethylbenzene was slowly added dropwise under reflux conditions, and the reaction was continued at reflux after completion of the dropwise addition. After completion of the reaction, the reaction system was cooled down to -50.0 °C. Subsequently, 2.2 mol (2.2 eq.) of trimethyl borate was slowly added dropwise and the reaction was kept at a low temperature until the feedstock was completely consumed. Upon completion of the reaction, the temperature was gradually increased and water was added to quench the reaction. Then, hydrochloric acid was added dropwise to adjust the pH to 1-2 and the reaction was continued with stirring. After completion of the reaction, the solvent was removed by rotary evaporation and the product was dried by filtration to give 0.90 mol of 3-methylphenylboronic acid as a white solid with 0.03% water content, 98.86% purity and 90.0% yield.

References

[1] Patent: CN106946924, 2017, A. Location in patent: Paragraph 0009; 0020; 0023; 0026
[2] Patent: US5183653, 1993, A

3-Tolylboronic acid(17933-03-8)Related Product Information

• 3,5-Dimethylbenzoic acid
• Methylboronic acid
• Triphenylphosphine
• Stearic acid
• Folic acid
• Phenylboronic acid
• Dichloromethylphenylsilane
• 3,5-Dimethylphenylboronic acid
• 3-Nitrophenylboronic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Zinc borate
• p-Toluenesulfonic acid
• Methyltriphenylphosphonium bromide
• 2,4,6-Trimethylphenylboronic acid
• Ethyl 3-methylbenzoate
• m-Tolualdehyde
• Citric acid
• Ascoric Acid