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| | 3-TRIMETHYLSILYL-2-PROPYN-1-OL Basic information |
| | 3-TRIMETHYLSILYL-2-PROPYN-1-OL Chemical Properties |
| Melting point | 63.5-65.0 °C | | Boiling point | 76 °C11 mm Hg(lit.) | | density | 0.865 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.451(lit.) | | Fp | 152 °F | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Benzene (Sparingly) | | form | Liquid | | pka | 13.71±0.10(Predicted) | | color | Clear yellow | | Specific Gravity | 0.865 | | Water Solubility | Not miscible with water. | | Sensitive | Moisture Sensitive | | Hydrolytic Sensitivity | 4: no reaction with water under neutral conditions | | BRN | 1902505 | | InChI | 1S/C6H12OSi/c1-8(2,3)6-4-5-7/h7H,5H2,1-3H3 | | InChIKey | ZVGCJDPEKKEYES-UHFFFAOYSA-N | | SMILES | C[Si](C)(C)C#CCO | | CAS DataBase Reference | 5272-36-6(CAS DataBase Reference) | | NIST Chemistry Reference | 3-Trimethylsilylpropargyl alcohol(5272-36-6) | | EPA Substance Registry System | 2-Propyn-1-ol, 3-(trimethylsilyl)- (5272-36-6) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 23-24/25-37/39-26 | | RIDADR | 2810 | | WGK Germany | 3 | | F | 8-10 | | TSCA | TSCA listed | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29319090 | | Storage Class | 10 - Combustible liquids |
| | 3-TRIMETHYLSILYL-2-PROPYN-1-OL Usage And Synthesis |
| Chemical Properties | clear yellow liquid | | Uses | Trimethylsilylpropargyl alcohol is used as a reagent to synthesize Isbogrel, a Thromboxane A 2 (TXA 2) synthase inhibitor and also a TXA 2 receptor antagonist that has potential to treat asthma. | | Application | 3-Trimethylsilyl-2-propyn-1-ol is a colourless transparent liquid which is sensitive to light, air and moisture, and can be used as raw material for organic synthesis or reaction reagent. Alkyllithiums undergo trans addition to 3-(trimethylsilyl)-2-propyn-1-ols to yield (1-lithiovinyl)silanes. Due to unidentified side-reactions, yields do not exceed 20%. | | Synthesis | Compound 5 (0.250 g, 1.17 mmol) was added dropwise to a flask containing methanol (4.0 mL) and Amberlyst-15 (0.025 g) under nitrogen protection at a reaction temperature of 0 °C. The reaction mixture was warmed to 40 °C and stirred for 8 hours. Upon completion of the reaction, the resin was removed by filtration and washed with ethyl acetate (10 mL). To the filtrate, 10% aqueous hydrochloric acid (10 mL) was added, followed by extraction of the organic layer with ethyl acetate (3 x 10 mL). The organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by column chromatography (eluent: hexane/ethyl acetate = 9:1) to afford compound 6 in 96% yield (0.143 g, 1.12 mmol). | | References | [1] Tetrahedron, 1996, vol. 52, # 21, p. 7487 - 7510
[2] Journal of the Brazilian Chemical Society, 2013, vol. 24, # 12, p. 1933 - 1941
[3] Chemistry - A European Journal, 2015, vol. 21, # 27, p. 9662 - 9665
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987, p. 1077 - 1082
[5] Journal of Organic Chemistry, 1995, vol. 60, # 14, p. 4650 - 4652 |
| | 3-TRIMETHYLSILYL-2-PROPYN-1-OL Preparation Products And Raw materials |
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