4-BROMOTHIOPHENE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

157-159℃

Boiling point:

318.0±27.0 °C(Predicted)

Density 

1.923±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

3.63±0.20(Predicted)

color 

Off-white/faint brown

InChI

InChI=1S/C5H3BrO2S/c6-4-2-9-1-3(4)5(7)8/h1-2H,(H,7,8)

InChIKey

APBIZVFQQBCAAT-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

WGK Germany 

2

Hazard Note 

Irritant

HS Code 

2934999090

4-BROMOTHIOPHENE-3-CARBOXYLIC ACID Usage And Synthesis

Synthesis

Cool 100 mL of ether to -78°C under a nitrogen atmosphere. A 1.6 M n-butyllithium solution (28.4 mL) was slowly added. Subsequently, a solution of 3,4-dibromothiophene (10 g, 41.3 mmol) dissolved in 50 mL of ether was added dropwise over 10 min. The reaction temperature was maintained at -78 °C and stirring was continued for 10 min before an excess (>50 g) of fresh powdered dry ice (CO?) was added. The reaction mixture was stirred at -78°C for 1 hour, then 30 mL of 1 M NaOH solution (pre-diluted with 100 mL of water) was slowly added (note: CO? will be released). Gradually increase the temperature until the ice melts. Separate the organic and aqueous phases and extract the ether phase with 25 mL of 1 N NaOH solution. Combine all aqueous phases and acidify with 100 mL of 1 N HCl solution to pH < 7. Collect the precipitated white precipitate by filtration, wash with water, and dry in a vacuum oven to give 4-bromothiophene-3-carboxylic acid as a white solid (5.8 g, 68% yield).

References

[1] Pharmazie, 2006, vol. 61, # 11, p. 901 - 907
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 19, p. 2735 - 2744
[3] Patent: WO2006/3096, 2006, A1. Location in patent: Page/Page column 71-72
[4] Patent: US2013/116233, 2013, A1. Location in patent: Paragraph 1018; 1019
[5] Patent: WO2014/140086, 2014, A1. Location in patent: Page/Page column 68-69

4-BROMOTHIOPHENE-3-CARBOXYLIC ACID(16694-17-0)Related Product Information

• 4-Acetylphenylboronic acid
• 3-Bromothiophene-2-carboxylic acid 98%,3-BROMOTHIOPHENE-2-CARBOXYLIC ACID,3-Bromothiophene-2-carboxylic acid ,98%
• 5-BROMOTHIOPHENE-2-CARBOXYLIC ACID
• 4-BROMOTHIOPHENE-3-CARBOXYLIC ACID
• 3-BROMOTHIOPHEN-2,4-DICARBOXYLIC ACID
• 5-bromothiophene-3-carboxylic acid
• 2-BROMOTHIOPHENE-3-CARBOXYLIC ACID
• 4-Nitro-5-bromothiophene-2-carboxylic acid methyl ester
• 2,3-Dihydro-3-oxo-2-chloro-4-bromothiophene-2-carboxylic acid methyl ester
• 5-BROMOTHIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER
• 2-BROMOTHIOPHENE-5-CARBOXYLIC ACID
• 3-Hydroxy-4-bromothiophene-2-carboxylic acid methyl ester
• SPECS AI-942/25034511
• SPECS AP-836/41220399
• 4-BROMO-2,5-DITERT-BUTYLTHIOPHENE-3-CARBOXYLIC ACID
• SPECS AI-942/25034125
• SPECS AI-942/25034096