3-Bromothioanisole Chemical Properties

Boiling point:

124-125 °C10 mm Hg(lit.)

Density 

1.51 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.628(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Chloroform, Ethyl Acetate

form 

clear liquid to slightly cloudy liquid

color 

Colorless to Yellow

Specific Gravity

1.510

Sensitive 

Stench

BRN 

2078598

CAS DataBase Reference

33733-73-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-37-26

RIDADR 

UN 3334

WGK Germany 

3

Hazard Note 

Irritant/Stench

HazardClass 

IRRITANT, STENCH

HS Code 

29309090

MSDS

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

3-Bromothioanisole Usage And Synthesis

Chemical Properties

Pale-Yellow Liquid

Uses

3-Bromothioanisole is a useful reagent for the preparation of (Z)-1,2-diborylalkenes via sodium-metal-promoted reductive 1,2-syn-diboration of alkynes with reduction-??resistant trimethoxyborane.

Synthesis

GENERAL METHOD: 3-bromophenylboronic acid (1.0 mmol), dimethyl disulfide (2.0 mmol), di-tert-butyl peroxide (DTBP, 3.0 mmol) and acetonitrile (CH3CN, 2.0 mL) were added sequentially to a sealed tube. The reaction mixture was stirred at 120 °C in air for 12 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with deionized water (5 mL) and subsequently extracted with ethyl acetate (EtOAc, 4 × 10 mL). The organic phases were combined, washed with saturated saline (3 × 10 mL), dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography with ethyl acetate/hexane as eluent (v/v = 1:30 to 1:100). The resulting 3-bromothioanisole was characterized by spectroscopic analyses (NMR hydrogen spectroscopy, carbon spectroscopy, etc.) and compared with the data of known compounds (see Supporting Information for details).

References

[1] Synlett, 2016, vol. 27, # 15, p. 2269 - 2273

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