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| | 4-BROMOTHIOPHENE-3-CARBOXYLIC ACID Basic information |
| Product Name: | 4-BROMOTHIOPHENE-3-CARBOXYLIC ACID | | Synonyms: | 4-BROMOTHIOPHENE-3-CARBOXYLIC ACID;4-bromo-3-thenoic acid;4-Bromothiophene-3-carvoxylic acid;4-Bromo-3-thiophenecarboxylicacid;4-Bromo-3-carboxythiophene;3-Thiophenecarboxylic acid, 4-broMo-;3-Bromo-4-carboxythiophene, 4-Bromo-3-thenoic acid;4-Bromothiophenecarboxylicacid | | CAS: | 16694-17-0 | | MF: | C5H3BrO2S | | MW: | 207.05 | | EINECS: | 240-739-8 | | Product Categories: | Carboxy;Organohalides;Thiophene | | Mol File: | 16694-17-0.mol |  |
| | 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 |
| Hazard Codes | Xi | | WGK Germany | 2 | | Hazard Note | Irritant | | HS Code | 2934999090 | | Storage Class | 11 - Combustible Solids |
| | 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 Preparation Products And Raw materials |
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