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| Type | HazMat fee for 500 gram (Estimated) |
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Structure of 96617-71-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 96617-71-9 |
| Formula : | C11H8F6O2 |
| M.W : | 286.17 |
| SMILES Code : | O=C(OCC)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 |
| English Name : | Ethyl 3,5-bis(trifluoromethyl)benzoate |
| MDL No. : | MFCD01320684 |
| GHS Pictogram: | |
| Signal Word: | |
| Hazard Statements: | |
| Precautionary Statements: | |
| Class: | |
| UN#: | |
| Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50% | Stage #1: (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one With sodium hydride In 1,2-dimethoxyethane; mineral oil for 1h; Reflux; Stage #2: 3,5-bis-trifluoromethylbenzoic acid ethyl ester In 1,2-dimethoxyethane; mineral oil for 3h; Reflux; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 55% | Stage #1: 3,5-bis(trifluoromethyl)iodobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: formic acid ethyl ester In tetrahydrofuran; hexane at -78℃; for 3h; Stage #3: With ethanol; iodine; potassium carbonate In tetrahydrofuran; hexane at -78 - 20℃; for 16h; | 4.2. Typical procedure for one-pot conversion of aromatic bromides into aromatic ethyl esters with ethyl formate General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3×20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77% yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 41% | With sodium hydride In tetrahydrofuran; mineral oil at 100℃; for 8h; | 43 5,6-Dihydro-cyclopenta[b]thiophen-4-one in 13 mL of THY was treated with NaH (60 percent, 1.1 g, 27 mmol). After the addition of 3,5-Bis-trifluoromethyl-benzoic acid ethyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(3,5-Bis-trifluoromethyl-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (1.07 g, 4.1 mmol) as yellow solid in 41% yield. |
| 41% | With sodium hydride In tetrahydrofuran; mineral oil at 100℃; for 8h; | 43 5,6-dihydro-cyclopenta [b] thiophen-4-one in 13 mL of THF was treated with NaH (60%, 1.1 g, 27 mmol). After the addition of 3,5-bis-trifluoromethyl-benzoic acid ethyl ester, the reaction mixture was heated to 100 & lt; 0 & gt; C and maintained for 8 hours. The solution was cooled to room temperature and poured into water. The product mixture was acidified with concentrated hydrochloric acid and ethyl acetate (70 mL) was added. The organic layer was collected, treated with brine, dried over MgSO4 (s) and concentrated under reduced pressure. The resulting precipitate was collected and recrystallized from ethanol to give the corresponding 5- (3,5-bis-trifluoromethyl-benzoyl) -5,6-dihydro-cyclopenta [b] thiophene- 4-one (1.07 g, 4.1 mmol) as a yellow solid in 41% yield. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran; mineral oil / 8 h / 100 °C 2: hydrazine hydrate; acetic acid / ethanol / 4 h / 100 °C / Inert atmosphere | ||
| Multi-step reaction with 2 steps 1: sodium hydride / mineral oil; tetrahydrofuran / 8 h / 100 °C 2: hydrazine hydrate; acetic acid / ethanol / 4 h / 100 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 65% | With chloro-trimethyl-silane; magnesium In N,N-dimethyl-formamide at 20℃; | General procedure for reductive carboxylation of ethyl benzoates (1) and benzoylformic acid (2a) General procedure: A typical procedure is as follows. Magnesium turnings (0.36 g, 15 mmol) for Grignard reagent with no pre-treatment were placed in a 100 mL four-necked flask and were heated to dry. Carbon dioxide was introduced to the flask and a balloon filled with carbon dioxide was attached to the flask. Chlorotrimethylsilane (3.17 mL, 25 mmol) in dry DMF (30 mL) was added to the flask and the reaction mixture was stirred for 30 minutes at room temperature. Ethyl benzoate 1a (0.72 mL, 5 mmol) was added dropwise by means of a syringe and the reaction mixture was stirred at room temperature until the starting material disappeared. Then the reaction mixture was carefully poured into 1 M hydrochloric acid solution (100 mL) and the product was extracted with diethyl ether (40 mL) four times. The combined organic layer was washed with 1 M potassium carbonate solution (40 mL) twice and the product was transferred to the water layer. To the combined water layers, 3 M hydrochloric acid (200 mL) was added and the product was extracted with ether (40 mL) four times. The combined ether layer was washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the product 2a. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 65% | Stage #1: Methyl p-tolyl sulfoxide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 3,5-bis-trifluoromethylbenzoic acid ethyl ester In hexane; ethyl acetate at -78℃; for 0.5h; Inert atmosphere; | 1. Chemistry. Synthesis of -ketosulfoxides. General Procedure General procedure: A freshly prepared solution of LDA (6.46 mmol, 2 eq.) in THF fromdiisopropylamine (7.11 mmol, 2.2 eq.) in THF (10 mL) at -78 °C and 2 M de nBuLi solution in hexane (3.23 mL, 6.46 mmol, 2 eq.), is added over the corresponding methyl sulfoxide (3.23 mmol, 1 eq.) in THF (10 mL), at -78°C, under argon. After stirring for 30 min. the formed carbanion solution is added over a THF solution (10 mL) of the corresponding ethyl carboxylate (3.23 mmol, 1 eq.), at -78°C, under argon. After stirring for 30 min., the reaction mixture was quenched with saturated NH4Cl, aqueous solution and 1M H2SO4 was added until pH 3-4. The aqueous phase was then extracted with EtOAc (5 x 50 mL), washed with saturated NaHCO3 aqueous solution and saturated NaCl aqueous solution, and dried over Na2SO4. After removing the solvent at vacuo, the residue was purified by flash chromatography, to give the corresponding -ketosulfoxide. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: piperidine / diethyl ether / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 51 g | With sulfuric acid for 10h; Reflux; | [Synthesis of Intermediate A] 3,5-bistrifluoromethylbenzoic acid 50.0 gEthanol 250 ml,And 5 ml of concentrated sulfuric acid were sequentially added.After heating refluxing for 10 hours,The solvent was distilled off under reduced pressure.250 ml of ethyl acetate was added to the residue,The organic layer was washed once with 200 ml of water,And washed twice with 200 ml of saturated aqueous sodium hydrogen carbonate solution.The organic layer was separated,It was dried using magnesium sulfate.Further, by performing concentration under reduced pressure,51 g of Intermediate A was obtained. |
Tags: 96617-71-9 | Ethyl 3,5-bis(trifluoromethyl)benzoate | Fluorinated Building Blocks | Aryls | Esters | Trifluoromethyls | Organic Building Blocks
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| P304 | IF INHALED: |
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| P378 | |
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| P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
| P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
| P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
| P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
| P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
| P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
| P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
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| H250 | Catches fire spontaneously if exposed to air |
| H251 | Self-heating; may catch fire |
| H252 | Self-heating in large quantities; may catch fire |
| H260 | In contact with water releases flammable gases which may ignite spontaneously |
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| H411 | Toxic to aquatic life with long-lasting effects |
| H412 | Harmful to aquatic life with long-lasting effects |
| H413 | May cause long-lasting harmful effects to aquatic life |
| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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