2-(Trimethylsilyl)thiazole CAS 79265-30-8
2-(Trimethylsilyl)thiazole Basic information
| Product Name: | 2-(Trimethylsilyl)thiazole |
| Synonyms: | 2-TST;2-THIAZOLYTRIMETHYLSILANE;2-Thiazolyltrimethylsilane;Thiazole, 2-(trimethylsilyl)-;2-（trimethyl)thiazole;2-TRIMETHYLSILYTHIAZOLE;Dondoni;2-Thiazolyltrimethylsilane, 2-TST |
| CAS: | 79265-30-8 |
| MF: | C6H11NSSi |
| MW: | 157.31 |
| EINECS: | |
| Product Categories: | Thiazoles, Isothiazoles & Benzothiazoles;API intermediates;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Building Blocks;C3 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Thiazoles;Thiazoles, Isothiazoles &Benzothiazoles |
| Mol File: | 79265-30-8.mol |
2-(Trimethylsilyl)thiazole Chemical Properties
| Boiling point | 56-57 °C10 mm Hg(lit.) |
| density | 0.985 g/mL at 25 °C(lit.) |
| refractive index | n |
| Fp | 135 °F |
| storage temp. | Inert atmosphere,2-8°C |
| solubility | THF: very soluble(lit.) |
| pka | 2.91±0.10(Predicted) |
| form | Liquid |
| color | Clear colorless to slightly yellow |
| Specific Gravity | 0.99 |
| Water Solubility | IMMISCIBLE |
| Hydrolytic Sensitivity | 7: reacts slowly with moisture/water |
| BRN | 3538017 |
| CAS DataBase Reference | 79265-30-8(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 23-24/25-26 |
| RIDADR | 1993 |
| WGK Germany | 3 |
| F | 10-21 |
| HazardClass | 3 |
| PackingGroup | III |
| HS Code | 29341000 |
| Chemical Properties | Colorless to light yellow liqui |
| Physical properties | bp 51–53 °C/10 mmHg; d 0.992 g mL?1; nD 1.4980. |
| Uses | 2-(Trimethylsilyl)thiazole is used as formyl anion equivalent; effective one-carbon homologating reagent of alkoxy aldehydes, amino aldehydes, anddialdoses.It takes part in the reactions of Homologation of Aldehydes, Metalation and Reactivity with Electrophiles, Cross-coupling Reactions, etc. |
| Preparation | Although 2-(trimethylsilyl)thiazole (1) iscommercially available, it can be easily prepared on a multigram scale from 2-bromothiazole, n-butyllithium, and chlorotrimethylsilane as shown in eq 1. |
| Synthesis | 288-47-1 75-77-4 79265-30-8 A solution of thiazole (5.03 g) dissolved in ether (59 mL) was slowly added dropwise to a mixture of n-butyllithium (2.5 M hexane solution, 24 mL) and ether (18 mL) at -78 °C. After completion of the dropwise addition, the reaction was kept at -78°C for 30 min. Subsequently, a solution of trimethylchlorosilane (TMSCl, 6.41 g) dissolved in ether (59 mL) was added at the same temperature. The reaction mixture was continued to be stirred at -78 °C for 1 h, followed by slow warming to room temperature. After completion of the reaction, the reaction mixture was washed with saturated sodium bicarbonate (NaHCO3) solution and the organic phase was dried with anhydrous sodium sulfate (Na2SO4). After removal of the solvent by decompression evaporation, the residue was subjected to decompression distillation (80 °C/14 mmHg) to afford the target product 2-(trimethylsilyl)thiazole (I-54) in 90% yield. The product was analyzed by GC-MS and showed the molecular ion peak (M+H)+ with m/z of 157.10. |
| References | [1] Patent: WO2011/79114, 2011, A1. Location in patent: Page/Page column 125 [2] Patent: WO2012/48129, 2012, A2. Location in patent: Page/Page column 385 [3] Tetrahedron Letters, 2008, vol. 49, # 1, p. 66 - 69 [4] Journal of Organic Chemistry, 1988, vol. 53, # 8, p. 1748 - 1761 [5] Patent: WO2009/21992, 2009, A2. Location in patent: Page/Page column 84 |
2-(Trimethylsilyl)thiazole Preparation Products And Raw materials
| Raw materials | Thiazole-->2-Bromothiazole-->Chlorotrimethylsilane-->Diethyl ether-->Hexane-->n-Butyllithium |
| Preparation Products | 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole-->ETHYL 2-CHLOROTHIAZOLE-5-CARBOXYLATE-->2-Cyanothiazole-->5-Bromothiazole-->Thiazole-5-carboxylic acid-->Methyl 6-(2-thiazolyl)-6-oxohexanoate-->Ethyl 4-(2-thiazolyl)-4-oxobutyrate-->pyridin-2-yl(thiazol-2-yl)Methanone-->Ethyl 2-oxo-2-(thiazol-2-yl)acetate |
