2-Bromo-5-methylthiophene Chemical Properties

Boiling point:

65 °C/15 mmHg (lit.)

Density 

1.552 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.569(lit.)

Flash point:

173 °F

storage temp. 

2-8°C

form 

Liquid Which May Contain Some Precipitate

Specific Gravity

1.552

color 

Yellow

InChI

InChI=1S/C5H5BrS/c1-4-2-3-5(6)7-4/h2-3H,1H3

InChIKey

ACDLOOGOFKSUPO-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

765-58-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

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

Safety Statements 

23-36/37/39-37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:2-Bromo-5-methylthiophene
• Language:English Provider:SigmaAldrich

2-Bromo-5-methylthiophene Usage And Synthesis

Uses

2-Bromo-5-methylthiophene is a heterocyclic compound that can be used as an intermediate in organic synthesis.

Chemical Properties

Yellow liquid

Synthesis

General procedure for the synthesis of 2-bromo-5-methylthiophene from 2-methylthiophene: A bromine solution was prepared by dissolving 48.0 g of bromine (0.3 mol) in 260 cm3 dioxane. This bromine solution was slowly added dropwise under stirring conditions to a solution of 29.4 g 2-methylthiophene (0.3 mmol) dissolved in 140 cm3 dioxane. The reaction mixture was stirred continuously for 3 hours at room temperature. Subsequently, the reaction system was cooled to 0 °C and saturated aqueous sodium bicarbonate solution was carefully added to neutralize the reaction. The mixture was extracted with ethyl acetate and the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent. The residue was purified by distillation to give 37.2 g 2-bromo-5-methylthiophene (0.21 mol, 70% yield). Boiling point: 68-70 °C (20 mbar). 1H NMR (400 MHz, CDCl3): δ = 2.42 (s, 3H), 6.51 (d, 1H, J = 3.6 Hz), 6.83 (d, 1H, J = 3.6 Hz) ppm. LC-MS: retention time tR = 1.65 min; MS: m/z = 176, 178 ([M+ 1]+, [M+3]+).

References

[1] Journal of Organic Chemistry, 2014, vol. 79, # 4, p. 1836 - 1841
[2] Synthesis, 2002, # 9, p. 1133 - 1135
[3] Green Chemistry, 2018, vol. 20, # 19, p. 4448 - 4452
[4] Synthesis, 2011, # 2, p. 207 - 209
[5] European Journal of Organic Chemistry, 2018, vol. 2018, # 20, p. 2592 - 2602

2-Bromo-5-methylthiophene(765-58-2)Related Product Information

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