5-Methylthianaphthene

5-Methylthianaphthene Property

Melting point:

35-36 °C

Boiling point:

71-73°C 0,6mm

Density 

1,111 g/cm³

refractive index 

1.6150 (estimate)

Flash point:

71-73°C/0.6mm

storage temp. 

2-8°C

form 

Low Melting Mass

color 

White

Water Solubility 

Insoluble in water.

λmax

303nm(Hexane)(lit.)

BRN 

109866

CAS DataBase Reference

14315-14-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzo[b]thiophene, 5-methyl-(14315-14-1)

EPA Substance Registry System

5-Methylbenzo[b]thiophene (14315-14-1)

Safety

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

36/37/39-26-22

Hazard Note 

Harmful

HS Code 

29309090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P321Specific treatment (see … on this label).

P405Store locked up.

5-Methylthianaphthene Chemical Properties,Usage,Production

Chemical Properties

white low melting mass

Uses

5-Methylbenzo[b]thiophene is useful in substituted thiophene for proteomics research.

Synthesis

Step 1: 5.2 g of bromoacetaldehyde diethyl acetal was dissolved in 10 mL of tetrahydrofuran and slowly added dropwise to a mixture containing 4.00 g of 4-methylbenzenethiol, 1.4 g of 60% sodium hydride (dispersed in mineral oil) and 35 mL of tetrahydrofuran. The reaction mixture was stirred at room temperature for 15 hours. Upon completion of the reaction, the reaction was quenched by the addition of 10 mL of saturated aqueous ammonium chloride, followed by three extractions with tert-butyl methyl ether. The organic phases were combined, washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent. Step 2: The above concentrated residue was added to a mixture of 5 g of phosphorus pentoxide and 10 g of phosphoric acid that had been preheated to 175°C and stirred for 45 minutes, and stirring was continued for 5 minutes. At the end of the reaction, the mixture was quenched by pouring it into ice water and extracted three times with tert-butyl methyl ether. The organic phases were combined, washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent. Step 3: The final residue was purified by silica gel column chromatography to give 2.77 g 5-methylbenzo[b]thiophene.

References

[1] Patent: US2015/282482, 2015, A1. Location in patent: Paragraph 2116; 2117