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| | Ethyl 4-Ethynylbenzoate Basic information |
| Product Name: | Ethyl 4-Ethynylbenzoate | | Synonyms: | Ethyl 4-Ethynylbenzoate;4-Ethynyl-benzoic acid ethyl ester;(p-Ethoxycarbonylphenyl)acetylene;4-(Ethoxycarbonyl)phenylacetylene;Ethyl 4-Ethynylbenzoate(WX686207);Benzoic acid, 4-ethynyl-, ethyl ester;Ethyl 4-ethynylbenzoate - [E54339] | | CAS: | 10602-03-6 | | MF: | C11H10O2 | | MW: | 174.2 | | EINECS: | | | Product Categories: | | | Mol File: | 10602-03-6.mol |  |
| | Ethyl 4-Ethynylbenzoate Chemical Properties |
| Melting point | 28 °C | | Boiling point | 257.1±23.0 °C(Predicted) | | density | 1.08±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | Appearance | Colorless to light yellow <28 °C Solid,>28 °C Liquid |
| | Ethyl 4-Ethynylbenzoate Usage And Synthesis |
| Synthesis | The general procedure for the synthesis of ethyl 4-alkynylbenzoate from the compound (CAS:150969-54-3) is as follows: firstly, the desired aryl-substituted terminal acetylene (5) was prepared using the Sonogashira reaction [1] as a precursor for the synthesis of betulinic acid 1,2,3-triazole library. Some of the acetylene (5a, 5b, 5c, 5g) can be purchased directly from commercial sources. This was done as follows: under argon protection, iodide 6 (500 mg) was reacted with trimethylmethylsilylacetylene (1.5 eq.) in the presence of Pd(PPh3)2Cl2 (2 mol%), CuI (4 mol%), and triethylamine (0.5 mL) in dry DMF at room temperature to produce intermediate 7. Subsequently, intermediate 7 was formed by reaction of iodide 6 with trimethylsilylacetylene (1.5 eq.) dissolved in anhydrous methanol (4.0 mL ) in anhydrous methanol (4.0 mL), the demethylsilylation reaction was achieved by treating intermediate 7 with a solution of K2CO3 (1 equiv.) to ultimately yield terminal acetylene 5. | | References | [1] Chemistry - A European Journal, 2011, vol. 17, # 34, p. 9320 - 9325
[2] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 93 - 105
[3] Patent: WO2009/149381, 2009, A2. Location in patent: Page/Page column 32
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 1, p. 211 - 224
[5] Journal of the American Chemical Society, 2015, vol. 137, # 1, p. 413 - 419 |
| | Ethyl 4-Ethynylbenzoate Preparation Products And Raw materials |
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