2,4-Dibromothiophene Chemical Properties

Melting point:

-26.3°C

Boiling point:

215°C

Density 

2.157 g/mL at 25 °C

refractive index 

1.631-1.633

Flash point:

215°C

storage temp. 

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

form 

liquid

Specific Gravity

2.149

color 

Colorless to Light yellow to Light orange

Water Solubility 

It is insoluble in water.

BRN 

107651

InChI

InChI=1S/C4H2Br2S/c5-3-1-4(6)7-2-3/h1-2H

InChIKey

WAQFYSJKIRRXLP-UHFFFAOYSA-N

SMILES

C1(Br)SC=C(Br)C=1

CAS DataBase Reference

3140-92-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi,T

Risk Statements 

36/37/38-20/21/22-41-37/38-25

Safety Statements 

36/37/39-26-36-45-39

RIDADR 

UN2810

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29349990

Storage Class

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects

Hazard Classifications

Acute Tox. 3 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:2,4-Dibromothiophene
• Language:English Provider:ACROS
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2,4-Dibromothiophene Usage And Synthesis

Chemical Properties

clear colorless to light brown liquid

Uses

2,4-Dibromothiophene is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is also used as an intermediate in organic synthesis.

Synthesis

2,3,5-Tribromothiophene (1):

120 g (1.43 mol) of thiophene was added to 240 mL of glacial acetic acid and 687 g (4.30 mol) of Br2 was added dropwise at 5-10 ??C, stirred at room temperature for 3 h and heated at reflux for 2 h. The residue was then evaporated under vacuum and distilled through a short Vigreux column. Subsequently, the glacial acetic acid was evaporated under vacuum and the residue was distilled through a short Vigreux column under water jet vacuum. Yield: 376.2 g (1.17 mol)1 (82%).

2,4-Dibromothiophene (4):

120 g (0.374 mol) of 2,3,5-tribromothiophene (1) was dissolved in 300 mL of ether, cooled to -30 ??C under N2, and 234 mL of a n-hexane solution of 6NBuLi (0.374 mol) was added dropwise over a period of 10 min at this temperature, stirred at -30 ??C for 5 minutes, poured into 1 L of cold water and extracted with ether 3 times. The combined ether phases were washed three times with water, dried with Na2SO4 and evaporated. The residue was fractionated on a 1 mVigreux flask under vacuum. Yield: 60 g (0.248 mol)4 (66%).

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