|
|
| | 5-Methylthiophene-2-boronic acid Basic information |
| | 5-Methylthiophene-2-boronic acid Chemical Properties |
| Melting point | 161.5-166.5 °C(lit.) | | Boiling point | 302.9±44.0 °C(Predicted) | | density | 1.25±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | | solubility | soluble in Methanol | | form | powder to crystal | | pka | 8.73±0.53(Predicted) | | color | White to Yellow to Orange | | BRN | 7019569 | | InChI | InChI=1S/C5H7BO2S/c1-4-2-3-5(9-4)6(7)8/h2-3,7-8H,1H3 | | InChIKey | NRIYPIBRPGAWDD-UHFFFAOYSA-N | | SMILES | B(C1SC(C)=CC=1)(O)O | | CAS DataBase Reference | 162607-20-7(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26-36-7/9-37 | | WGK Germany | 3 | | Hazard Note | Irritant | | HazardClass | IRRITANT, KEEP COLD | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids |
| | 5-Methylthiophene-2-boronic acid Usage And Synthesis |
| Chemical Properties | white to light yellow powder | | Uses | suzuki reaction | | Uses | Reactant for:
- Suzuki-Miyaura cross-coupling reactions
| | Synthesis | General procedure for the synthesis of 5-methylthiophene-2-boronic acid from 2-methylthiophene and triethyl borate: 5-methylthiophene-2-boronic acid (4.42 g, 85% yield) was obtained by reacting 2-methylthiophene (3.6 g, 17.3 mmol) with n-butyllithium at -78 °C, followed by the addition of triethyl borate. Next, 5-methylthiophene-2-boronic acid (4.42 g) was reacted with methyl 5-bromo-2-iodobenzoate at 80 °C via Suzuki coupling reaction to synthesize intermediate 1 (7.78 g, 80% yield). Intermediate 1 was subsequently cyclized with CH3MgCl to give Intermediate 2 (3.14 g, 40% yield). Finally, intermediate 2 was reacted with 9-phenylanthracene boronic acid via Suzuki coupling to give compound 1 (3.3 g, 60% yield). The structure of compound 1 was confirmed by 1HNMR and mass spectrometry (MS). | | References | [1] Patent: KR2015/96594, 2015, A. Location in patent: Paragraph 0290; 0291; 0292 |
| | 5-Methylthiophene-2-boronic acid Preparation Products And Raw materials |
|