2-Methylthiophenylboronic acid Chemical Properties

Melting point:

77-83 °C (lit.)

Boiling point:

215C

Density 

1,087g/cm

refractive index 

1,423-1,425

storage temp. 

Inert atmosphere,2-8°C

Water Solubility 

Slightly soluble in water

form 

Crystalline Powder

pka

8.50±0.58(Predicted)

color 

White

BRN 

8309529

InChI

InChI=1S/C7H9BO2S/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5,9-10H,1H3

InChIKey

QXBWTYBCNFKURT-UHFFFAOYSA-N

SMILES

B(C1=CC=CC=C1SC)(O)O

CAS DataBase Reference

168618-42-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-36-7/9-37/39-22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Methylthiophenylboronic acid Usage And Synthesis

Chemical Properties

White crystalline powde

Uses

suzuki reaction

Uses

Reactant for:

• Palladium-catalyzed cross-coupling reactions
• Suzuki-Miyaura coupling reactions

Synthesis

Part A: Preparation of 2-methylthiophenylboronic acid. 2-Bromothioanisole (29.0 g, 143 mmol) was dissolved in anhydrous tetrahydrofuran (400 mL) and the solution was cooled to -75°C. n-Butyllithium (62.0 mL, 2.5 M hexane solution, 155 mmol) was added slowly over 50 minutes. After stirring for 25 min, triisopropyl borate (46 mL, 199 mmol) was added dropwise over 35 min. The cold bath was removed and the reaction mixture was stirred at room temperature for 16 hours. The resulting solution was cooled in an ice bath and 6 M hydrochloric acid (100 mL) was added. The mixture was stirred at room temperature for 5 hours and then concentrated to half the original volume. The concentrate was partitioned between ether and water. The organic layer was extracted with 2 M sodium hydroxide solution, subsequently acidified with 6 M hydrochloric acid, concentrated again, and extracted several times with ether. The ether extracts were combined, dried with sodium sulfate, filtered and the solvent evaporated to give a beige solid product (20.4 g, 85% yield).1H-NMR (CDCl3) δ: 8.01 (dd, 1H, J = 7.3, J' = 1.4), 7.53 (dd, 1H, J = 7.7, J' = 1.1), 7.43 (td, 1H, J = 7.3, J' = 1.8), 7.34 (td, 1H, J = 7.3, J'= 1.5), 6.22 (s, 2H), 2.50 (s, 3H).

References

[1] Patent: EP946508, 2009, B1. Location in patent: Page/Page column 60
[2] Patent: EP1491187, 2004, A1. Location in patent: Page 26

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