5-Methylthiophene-2-boronic acid Chemical Properties

Melting point:

161.5-166.5 °C(lit.)

Boiling point:

302.9±44.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

8.73±0.53(Predicted)

color 

White to Yellow to Orange

BRN 

7019569

InChI

InChI=1S/C5H7BO2S/c1-4-2-3-5(9-4)6(7)8/h2-3,7-8H,1H3

InChIKey

NRIYPIBRPGAWDD-UHFFFAOYSA-N

SMILES

B(C1SC(C)=CC=1)(O)O

CAS DataBase Reference

162607-20-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

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

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29349990

MSDS

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

5-Methylthiophene-2-boronic acid Usage And Synthesis

Chemical Properties

white to light yellow powder

Uses

suzuki reaction

Uses

Reactant for:

• Suzuki-Miyaura cross-coupling reactions

Synthesis

General procedure for the synthesis of 5-methylthiophene-2-boronic acid from 2-methylthiophene and triethyl borate: 5-methylthiophene-2-boronic acid (4.42 g, 85% yield) was obtained by reacting 2-methylthiophene (3.6 g, 17.3 mmol) with n-butyllithium at -78 °C, followed by the addition of triethyl borate. Next, 5-methylthiophene-2-boronic acid (4.42 g) was reacted with methyl 5-bromo-2-iodobenzoate at 80 °C via Suzuki coupling reaction to synthesize intermediate 1 (7.78 g, 80% yield). Intermediate 1 was subsequently cyclized with CH3MgCl to give Intermediate 2 (3.14 g, 40% yield). Finally, intermediate 2 was reacted with 9-phenylanthracene boronic acid via Suzuki coupling to give compound 1 (3.3 g, 60% yield). The structure of compound 1 was confirmed by 1HNMR and mass spectrometry (MS).

References

[1] Patent: KR2015/96594, 2015, A. Location in patent: Paragraph 0290; 0291; 0292

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