2-(HYDROXYMETHYL)BENZO[B]THIOPHENE Chemical Properties

Melting point:

98-101°C

Boiling point:

108-110 °C(Press: 4 Torr)

Density 

1.294±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

13.89±0.10(Predicted)

color 

White to Orange to Green

CAS DataBase Reference

17890-56-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

HS Code 

29349990

2-(HYDROXYMETHYL)BENZO[B]THIOPHENE Usage And Synthesis

Chemical Properties

White to yellow solid

Uses

Benzo[b]thiophene-2-methano is an important intermediates and reagents in organic synthesis.

Synthesis

The general procedure for the synthesis of 1-benzothiophene-2-methanol using ethyl benzo[b]thiophene-2-carboxylate as a starting material was as follows: lithium aluminum hydride (712 mg) was suspended in dry tetrahydrofuran (15 mL) and cooled to 0°C in an ice bath. At this temperature, a solution of ethyl benzo[b]thiophene-2-carboxylate (2.06 g, 10 mmol) in tetrahydrofuran (15 mL) was slowly added dropwise. After the dropwise addition was completed, the reaction was kept at 0°C and stirring was continued for 1 hour. Subsequently, the reaction was quenched by careful addition of 1N hydrochloric acid (150 mL) and stirring was continued for 15 minutes. The reaction mixture was extracted with ethyl acetate, the organic layers were combined and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give the white crystalline product 1-benzothiophene-2-methanol (1.51 g, 92% yield). The product was characterized by 1H-NMR (CDCl3, 270 MHz) with chemical shifts of δ= 7.86-7.67 (m, 2H), 7.42-7.20 (m, 3H), 4.91 (s, 2H), 2.02 (bs, 1H).

References

[1] Patent: US2003/109570, 2003, A1
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 457 - 465
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2922 - 2926
[4] Organic Letters, 2016, vol. 18, # 8, p. 1828 - 1831
[5] Synlett, 2017, vol. 28, # 1, p. 133 - 137

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