2-Acetyl-5-bromothiophene Chemical Properties

Melting point:

94-96 °C (lit.)

Boiling point:

103 °C/4 mmHg (lit.)

Density 

1.649 (estimate)

Flash point:

103°C/4mm

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

soluble in Methanol

form 

Crystalline Flakes or Powder

color 

Yellow

Sensitive 

Light Sensitive

BRN 

113949

InChI

InChI=1S/C6H5BrOS/c1-4(8)5-2-3-6(7)9-5/h2-3H,1H3

InChIKey

IGBZCOWXSCWSHO-UHFFFAOYSA-N

SMILES

C(=O)(C1SC(Br)=CC=1)C

CAS DataBase Reference

5370-25-2(CAS DataBase Reference)

NIST Chemistry Reference

2-Acetyl-5-bromothiophene(5370-25-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

36/37/39-26-22

RIDADR 

UN2811

WGK Germany 

3

HazardClass 

LIGHT SENSITIVE

HS Code 

29339900

MSDS

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

2-Acetyl-5-bromothiophene Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-Acetyl-5-bromothiophene was used as a starting reagent in the synthesis of bithiophene bis-imidazo[1,2-a]pyridine derivatives. It was also used in the preparation of phosphorus-containing fused bicyclic 5,6-membered compounds.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 18, p. 1345, 1981 DOI: 10.1002/jhet.5570180714
Synthetic Communications, 11, p. 29, 1981 DOI: 10.1080/00397918108064279

Synthesis

The general procedure for the synthesis of 2-acetyl-5-bromothiophene from 2-acetylthiophene was as follows: 2-acetylthiophene (1.08 mL, 10 mmol), N-bromosuccinimide (NBS) (1.78 g, 30 mmol), and acetic anhydride (3.78 mL, 40 mmol) were added sequentially to a dry, 25 mL round-bottomed flask, which was equipped with a protective tube. Acetic acid (0.40 mL) was subsequently added to the mixture. The reaction mixture was stirred at 50 °C for 1 h protected from light and the color of the solution was observed to change from colorless to light yellow. Upon completion of the reaction, the mixture was cooled to room temperature and poured into 100 mL of water with continuous stirring until the acetic anhydride was completely hydrolyzed. At this point, 2-acetyl-5-bromothiophene precipitated as white crystals. The product was collected by filtration and washed in batches with 50 mL of water to give a final yield of 82%. The melting point of the product was 92-94 °C (acetone).1H NMR (300 MHz, CDCl3) data were as follows: δ 7.40 (d, J=3.9 Hz, 1H), 7.08 (d, J=3.9 Hz, 1H), 2.48 (s, 3H).

References

[1] Tetrahedron Letters, 2010, vol. 51, # 1, p. 205 - 208
[2] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9180 - 9187
[3] Tetrahedron Letters, 2014, vol. 55, # 5, p. 996 - 1001
[4] Tetrahedron Letters, 2014, vol. 55, # 5, p. 996 - 1001
[5] Organic Letters, 2013, vol. 15, # 9, p. 2108 - 2111

2-Acetyl-5-bromothiophene(5370-25-2)Related Product Information

• Acetyl coenzyme A sodium salt
• N-ACETYL-L-TYROSINE ETHYL ESTER
• Acetylacetone
• Methyl acrylate
• PIPERACETAZINE (250 MG)
• Cephalothin sodium
• Acetyl chloride
• Methylparaben
• 2-Acetylthiophene
• Bensulfuron methyl
• Kresoxim-methyl
• Tetrahydrothiophene
• Methyl
• tributyl acetocitrate
• Parathion-methyl
• 2-BROMO-1-(5-BROMOTHIOPHEN-2-YL)ETHANONE
• 2-BROMO-5-BENZOYLTHIOPHENE
• Methyl bromide