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| | Ethyl 4-iodobenzoate Basic information |
| | Ethyl 4-iodobenzoate Chemical Properties |
| Melting point | 267 °C | | Boiling point | 281-283 °C | | density | 1.641 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.5880(lit.) | | Fp | >230 °F | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Chloroform, Dichloromethane, Ethyl Acetate, Hexane | | form | Liquid | | Specific Gravity | 1.66 | | color | Clear colorless to yellow | | Water Solubility | insoluble | | Sensitive | Light Sensitive | | BRN | 2208568 | | InChI | 1S/C9H9IO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2H2,1H3 | | InChIKey | YCBJOQUNPLTBGG-UHFFFAOYSA-N | | SMILES | CCOC(=O)c1ccc(I)cc1 | | CAS DataBase Reference | 51934-41-9(CAS DataBase Reference) | | NIST Chemistry Reference | Ethyl 4-iodobenzoate(51934-41-9) |
| Hazard Codes | N,Xi,C | | Risk Statements | 51/53-36/37/38 | | Safety Statements | 61-24/25 | | RIDADR | UN 3082 9/PG 3 | | WGK Germany | 3 | | F | 8 | | Hazard Note | Irritant | | HazardClass | IRRITANT, LIGHT SENSITIVE | | HS Code | 29163990 | | Storage Class | 10 - Combustible liquids |
| | Ethyl 4-iodobenzoate Usage And Synthesis |
| Chemical Properties | Light Yellow Oil | | Uses | Ethyl 4-iodobenzoate can be used in the synthesis of biphenyl derivatives via Negishi cross coupling with the intermediates of the type ArMg(tmp)·2LiCl (tmp = trimethylolpropane). It can also be used as a starting material in the synthesis of p-carbomethoxyphenylmagnesium bromide, a polyfunctional organometallic reagent that can be used as building block in the synthesis of complex target molecules. | | Synthesis | General procedure for the synthesis of ethyl p-iodobenzoate from ethyl 4-bromobenzoate: under nitrogen protection, Cu2O (7.2 mg, 10 mol%), L-proline (11.5 mg, 20 mol%), ethyl 4-bromobenzoate (0.50 mmol), potassium iodide (KI, 249 mg, 0.75 mmol) and ethanol (EtOH, 1.5 mL). After sealing the Schlenk tube with a PTFE valve, the reaction mixture was stirred at 110 °C and the reaction process was monitored by gas chromatography (GC) analysis. Upon completion of the reaction, the yield was determined by GC using an appropriate internal standard (e.g., chlorobenzene or 1-chloro-4-methylbenzene) for highly volatile products; or the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent ratio of petroleum ether/ethyl acetate = 10/1) to obtain the target product ethyl p-iodobenzoate. | | References | [1] Catalysis Today, 2016, vol. 274, p. 129 - 132
[2] Chemical Communications, 2012, vol. 48, # 33, p. 3993 - 3995
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 1, p. 263 - 266
[4] Angew. Chem., 2015, vol. 127, # 01, p. 265 - 268,4
[5] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 2110 - 2117 |
| | Ethyl 4-iodobenzoate Preparation Products And Raw materials |
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