5-Bromothiophene-2-carbaldehyde Chemical Properties

Melting point:

55°C

Boiling point:

105-107 °C11 mm Hg(lit.)

Density 

1.607 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.637(lit.)

Flash point:

210 °F

storage temp. 

2-8°C

solubility 

Soluble in chloroform and methanol.

form 

Liquid After Melting

color 

Clear yellow to brown

Sensitive 

Air Sensitive

BRN 

108404

InChIKey

GFBVUFQNHLUCPX-UHFFFAOYSA-N

LogP

2.566 (est)

CAS DataBase Reference

4701-17-1(CAS DataBase Reference)

NIST Chemistry Reference

5-Bromo-2-thiophenecarboxaldehyde(4701-17-1)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

36/37/39-26-22-36

WGK Germany 

3

Hazard Note 

Irritant/Air Sensitive

TSCA 

N

HS Code 

29349990

MSDS

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

5-Bromothiophene-2-carbaldehyde Usage And Synthesis

Chemical Properties

clear yellow to brown liquid after melting

Uses

5-Bromo-2-thiophenecarboxaldehyde was used to prepare 5-[18F]fluoro-2-2-thiophene carboxaldehyde. Also is used in biological studies as anti-inflammatory and anti-tumor activity of the marine mangrove Rhizophora apiculata.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 1422, 1950 DOI: 10.1021/ja01159a527

Synthesis

2.1.1 Synthesis of 5-bromo-2-thiophenecarboxaldehyde Under nitrogen protection, 2-thiophenecarboxaldehyde (6.0 g, 53.5 mmol) was dissolved in anhydrous chloroform (125 mL). Subsequently, N-bromosuccinimide (10.4 g, 58.9 mmol) was slowly added and the reaction mixture was stirred for 12 h at room temperature. After completion of the reaction, the mixture was extracted with chloroform (3 × 50 mL), and the organic phases were combined and washed with deionized water (2 × 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using chloroform as eluent to afford 5-bromo-2-thiophenecarboxaldehyde as a colorless oil (10.0 g, 98% yield). 1H NMR (400 MHz, CDCl3): δ 7.20 (d, 1H, J = 4.0 Hz), 7.53 (d, 1H, J = 8.0 Hz), 9.79 (s, 1H).

References

[1] Physica B: Condensed Matter, 2017, vol. 519, p. 53 - 58
[2] Tetrahedron, 2007, vol. 63, # 37, p. 9188 - 9194
[3] Tetrahedron Letters, 2005, vol. 46, # 12, p. 1989 - 1992
[4] Patent: WO2018/67786, 2018, A1. Location in patent: Page/Page column 134; 135
[5] Journal of the Chemical Society, 1958, p. 1721

5-Bromothiophene-2-carbaldehyde(4701-17-1)Related Product Information

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• 2-Thiophenecarboxaldehyde
• Thifensulfuron methyl
• Tetrahydrothiophene
• 5-Bromothiazole
• Ethyl 5-bromothiophene-2-carboxylate
• 5-Bromothiophenesulfonyl chloride
• 5-Bromothiophene-2-sulfonamide
• METHYL4,5-DIBROMOTHIOPHENE-2-CARBOXYLATE
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• 2-Acetyl-5-bromothiophene
• 2-BROMO-1-(5-BROMOTHIOPHEN-2-YL)ETHANONE
• 4,5-DIBROMOTHIOPHENE-2-CARBOXALDEHYDE
• 5-Bromothiophene-2-carbohydrazide
• 5-Bromo-2-thiophenecarboxylic acid
• 4,5-DIBROMOTHIOPHENE-2-CARBOXYLIC ACID
• METHYL 4,5-DIBROMO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE
• Bromine