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| | 3-Bromo-1-(trimethylsilyl)-1-propyne Basic information |
| | 3-Bromo-1-(trimethylsilyl)-1-propyne Chemical Properties |
| Melting point | <0°C | | Boiling point | 44-45 °C2 mm Hg(lit.) | | density | 1.17 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.483(lit.) | | Fp | 145 °F | | storage temp. | 2-8°C | | solubility | Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly) | | form | Oil | | color | Colourless to Pale Yellow | | Specific Gravity | 1.351 | | Water Solubility | Immiscible with water. | | Hydrolytic Sensitivity | 4: no reaction with water under neutral conditions | | BRN | 2037650 | | Stability: | Hygroscopic | | InChI | 1S/C6H11BrSi/c1-8(2,3)6-4-5-7/h5H2,1-3H3 | | InChIKey | GAPRPFRDVCCCHR-UHFFFAOYSA-N | | SMILES | C[Si](C)(C)C#CCBr | | CAS DataBase Reference | 38002-45-8(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-28-36/37/39 | | RIDADR | UN 3334 | | WGK Germany | 3 | | F | 8-9-19 | | TSCA | No | | HS Code | 29319090 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 3-Bromo-1-(trimethylsilyl)-1-propyne Usage And Synthesis |
| Chemical Properties | Clear colorless to pale yellow liquid | | Uses | 3-Bromo-1-(trimethylsilyl)-1-propyne may be used in the preparation of tetrahydroisoquinoline-3-carboxylic acid derivatives. It may be used as reagent for the alkylation of dianion of β-keto esters at γ-carbon. It may be employed in the preparation of terminal conjugated enynes and allenic alcohols. | | General Description | 3-Bromo-1-(trimethylsilyl)-1-propyne is reported as a propargylating agent. Selective reaction of 3-bromo-1-(trimethylsilyl)-1-propyne with α-keto ester using indium metal has been studied. | | Synthesis | The general procedure for the synthesis of 3-bromo-1-trimethylsilyl-1-propyne from trimethylsilylpropargyl alcohol was as follows: To a solution of anhydrous dichloromethane (46.0 mL) containing triphenylphosphine (9.735 g, 37.11 mmol) under nitrogen atmosphere, bromine (5.438 g, 34.03 mmol) was slowly added at 0 °C. After 30 min of reaction, when the color of the solution changed from orange to white, trimethylsilylpropynol (3.960 g, 30.93 mmol) was slowly added. The reaction mixture was continued to be stirred for 1 h, followed by washing with water (3 × 30 mL) and 10% aqueous hydrochloric acid (2 × 20 mL) sequentially. The aqueous layer was extracted with ethyl acetate (3 x 20 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using hexane as eluent to afford 3-bromo-1-trimethylsilyl-1-propyne in 70% yield (4.125 g, 21.6 mmol). | | References | [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8122 - 8126
[2] Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13692 - 13696
[3] Tetrahedron, 1996, vol. 52, # 35, p. 11601 - 11624
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6127 - 6130
[5] Bulletin de la Societe Chimique de France, 1993, vol. 130, # 2, p. 154 - 159 |
| | 3-Bromo-1-(trimethylsilyl)-1-propyne Preparation Products And Raw materials |
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