2-Bromothioanisole Chemical Properties

Melting point:

-24 °C (lit.)

Boiling point:

145-146 °C/27 mmHg (lit.)

Density 

1.522 g/mL at 25 °C (lit.)

refractive index 

1.632-1.634

Flash point:

>110°C

storage temp. 

Inert atmosphere,Room Temperature

form 

Liquid

Specific Gravity

1.522

color 

Clear colorless to yellow

BRN 

2243716

InChI

InChI=1S/C7H7BrS/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3

InChIKey

ALAQDUSTXPEHMH-UHFFFAOYSA-N

SMILES

C1(Br)=CC=CC=C1SC

CAS DataBase Reference

19614-16-5(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-bromo-2-(methylthio)-(19614-16-5)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26

RIDADR 

UN 3334

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, STENCH

HS Code 

29309090

MSDS

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

2-Bromothioanisole Usage And Synthesis

Chemical Properties

clear yellow liquid

Uses

2-Bromothioanisole has been used in the preparation of:

• thioether-methyleneborane (PhSCH₂B (C₆F₅)₂)₂
• 1-dimesitylboryl-2-methylthio-benzene

Synthesis

Under argon protection, sodium hydroxide (0.32 g, 7.9 mmol) was dissolved in ethanol (3.0 mL), and 2-bromothiophenol (1.0 g, 5.29 mmol) was added slowly and stirred for 30 min at room temperature. Subsequently, iodomethane (0.5 mL, 7.9 mmol) was added and the reaction continued to be stirred at room temperature for 3 hours. Upon completion of the reaction, the reaction was quenched by the addition of ice water (4.0 mL) and the reaction mixture was extracted with dichloromethane (10 mL x 3). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography (eluent: petroleum ether) to afford the target compound 2-bromothioanisole.

References

[1] Macromolecules, 2002, vol. 35, # 1, p. 67 - 78
[2] Tetrahedron Asymmetry, 2011, vol. 22, # 5, p. 575 - 579
[3] Patent: WO2015/86525, 2015, A1. Location in patent: Page/Page column 127
[4] Tetrahedron Asymmetry, 1999, vol. 10, # 6, p. 1051 - 1060
[5] Organic Letters, 2005, vol. 7, # 1, p. 143 - 145

2-Bromothioanisole(19614-16-5)Related Product Information

• Bensulfuron methyl
• Tetrabromobisphenol A bis(dibromopropyl ether)
• Thioacetamide
• Dimethyl sulfide
• Guaiacol
• Hydrogen Sulfide
• Kresoxim-methyl
• Decabromodiphenyl oxide
• Sodium sulfide
• Butylated hydroxyanisole
• Methylparaben
• Anisole
• 2-Bromoanisole
• 4-Methoxyphenol
• Thioanisole
• CARBONYL SULFIDE
• Thiophanate-methyl
• Anise oil