2,3,5-Tribromothiophene Chemical Properties

Melting point:

25-28 °C (lit.)

Boiling point:

120 °C/11 mmHg (lit.)

Density 

2.483 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.664(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

solid

Specific Gravity

2.483

color 

White or Colorless to Yellow

BRN 

111486

InChI

InChI=1S/C4HBr3S/c5-2-1-3(6)8-4(2)7/h1H

InChIKey

SKDNDSLDRLEELJ-UHFFFAOYSA-N

SMILES

C1(Br)SC(Br)=CC=1Br

CAS DataBase Reference

3141-24-0(CAS DataBase Reference)

EPA Substance Registry System

Thiophene, 2,3,5-tribromo- (3141-24-0)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

36/37/39-26

RIDADR 

UN 2929 6.1/PG 2

WGK Germany 

3

TSCA 

T

HazardClass 

IRRITANT

HazardClass 

6.1

HS Code 

29349990

MSDS

• Language:English Provider:2,3,5-Tribromothiophene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,3,5-Tribromothiophene Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2,3,5-Tribromothiophene was used in the synthesis of 2,5-bis(dicyanomethylene)-3-bromo-2,5-dihydrothiophene.

Synthesis

a. Add 35 L of chloroform, thiophene and 16.8 kg of copper bromide to Reactor 1 and stir for 10 minutes. Reactor 1 was cooled to -5°C, followed by the slow dropwise addition of 65.0 kg of bromine. b. Upon start of the reaction, pass air or oxygen into Reactor 1. After completion of the bromine addition, the reaction was slowly heated to reflux and the reaction gas was condensed through reflux condenser 8 and returned to reactor 1. The reaction lasted for 3.5 hours and then cooled to 23-25°C. c. A drop of bromine was added to reactor 1 and the reaction was cooled to -5°C for 10 minutes. c. Add 10 L of 0.05 mol/L ethanol solution of sodium hydroxide dropwise to reaction kettle 1 to decompose unreacted bromine and stir for 30 min. d. Transfer the reaction mixture to autoclave 2, add 35 L of water, stir for 30 minutes and leave to stand. The lower organic phase was separated for atmospheric pressure distillation. During distillation, the solvent was first recovered by condensing through distillation condenser 9 and distillation condenser 10, and the solvent was recovered to solvent recovery tank 4. Subsequently, the distillation was carried out under reduced pressure at 15 mmHg, and again condensed through distillation condenser 9 and distillation condenser 10, and the fraction at 112-116 °C/15 mmHg was collected to the product fraction collection tank 5, which ultimately yielded 52.6 kg of colorless liquid 2,3,5-tribromo thiophene.

References

[1] European Journal of Inorganic Chemistry, 2001, # 1, p. 233 - 238
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 4, p. 861 - 870
[3] Synthetic Communications, 1988, vol. 18, # 15, p. 1763 - 1764
[4] European Journal of Organic Chemistry, 2008, # 5, p. 801 - 804
[5] Chinese Journal of Chemistry, 2014, vol. 32, # 4, p. 365 - 369

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