5-BROMOBENZO[B]THIOPHENE Chemical Properties

Melting point:

47-48°C

Boiling point:

105-107°C 10mm

Density 

1.649±0.06 g/cm3(Predicted)

Flash point:

105-107°C/10mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Toluene

form 

powder to crystal

color 

White to Light yellow to Light orange

Sensitive 

Light Sensitive

BRN 

112878

InChI

InChI=1S/C8H5BrS/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5H

InChIKey

RDSIMGKJEYNNLF-UHFFFAOYSA-N

SMILES

C12=CC=C(Br)C=C1C=CS2

CAS DataBase Reference

4923-87-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

Hazard Note 

Irritant

HS Code 

29349990

MSDS

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5-BROMOBENZO[B]THIOPHENE Usage And Synthesis

Chemical Properties

white solid

Uses

5-Bromobenzo[b]thiophene is used as a reactant in the preparation of 4-aminoquinolines and tetraoxanes displaying antimalarial activity.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 1271, 1988 DOI: 10.1002/jhet.5570250445

Synthesis

A mixture of phosphoric acid (218 g) and chlorobenzene (2 L) was heated at 130??C and then treated with the product from Example 165A (107.0 g) for 2 hours using a syringe pump. The mixture was heated at 130??C for 15 hours. Water was removed from the mixture using a Dean-Stark trap at the start of reflux. The mixture was cooled to room temperature and quenched with 400 mL of water. The bottom aqueous layer was extracted with 200 mL of dichloromethane. The combined organic layers were washed with 200 mL of 10% Na2CO3 and concentrated to a brown oil (129.4 g). The crude oil was dissolved in 1 L of 10:90 EtOAC:hexane, filtered through a short pad of silica gel and concentrated. Further purification by column chromatography (silica gel, 5:95EtOAc:hexane) afforded 5-bromobenzo[b]thiophene yellow oil in yield (85.54 g, 95.8%).

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