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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.
Synonyms: Clorofene
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| CAS No. : | 120-32-1 |
| Formula : | C13H11ClO |
| M.W : | 218.68 |
| SMILES Code : | OC1=CC=C(Cl)C=C1CC2=CC=CC=C2 |
| Synonyms : |
Clorofene
|
| MDL No. : | MFCD00020140 |
| InChI Key : | NCKMMSIFQUPKCK-UHFFFAOYSA-N |
| Pubchem ID : | 8425 |
| GHS Pictogram: |
|
| Signal Word: | Danger |
| Hazard Statements: | H302-H315-H318-H335-H410 |
| Precautionary Statements: | P261-P273-P280-P305+P351+P338 |
| Class: | 9 |
| UN#: | 3077 |
| Packing Group: | Ⅲ |
* 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 |
|---|---|---|
| Surprisingly, it has now been found that new active compound combinations of at least one phenol derivative such as, for example, ... 3-methyl-4-chlorophenol o-phenylphenol m-phenylphenol p-phenylphenol 2-benzyl-4-chlorophenol | ||
| Examples of fungicides with which the 4-nitro-2-trichloromethylphenylsulfenamides according to the invention may be combined are as follows: ... barium salt of pentachlorophenol pentachlorophenyl acetate pentachlorobenzyl alcohol di-(5-chloro-2-hydroxyphenyl)-methane phenyl-(5-chloro-2-hydroxyphenyl)-methane N-trichloromethylthiotetrahydrophthalimide N-trichloromethylthiophthalimide N-fluorodichloromethylthiophthalimide ... | ||
| Examples of fungicides which can be combined with the compounds of the invention are: ... barium salt of pentachlorophenol (5B) pentachlorophenyl acetate pentachlorobenzyl alcohol di-(5-chloro-2-hydroxyphenyl)-methane (dichlorophen) phenyl-(5-chloro-2-hydroxyphenyl)-methane N-trichloromethylthiotetrahydrophthalimide (captan) N-trichloromethylthiophthalimide (folpet) N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide (captafol) ... |
| The following list of fungicides with which the N-(fluorodichloromethylthio)-benzanilides of the invention may be combined is intended to illustrate, but not restrict, possible combinations: ... barium salt of pentachlorophenol (5 B) pentachlorophenyl acetate pentachlorobenzyl alcohol di-(5-chloro-2-hydroxyphenyl)-methane (dichlorophen) phenyl-(5-chloro-2-hydroxyphenyl)-methane N-trichloromethylthiotetrahydrophthalimide (captan) N-trichloromethylthiophthalimide (folpet) N-fluorodichloromethylthio phthalimide ... |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate; potassium iodide; In acetone; for 20h;Heating / reflux; | 5 g of 2-benzyl-4-chlorophenol, 2.6 ml of chloroacetone, 1.38 g of potassium carbonate and 0.34 g of potassium iodide are dissolved in 50 ml of acetone and boiled under reflux for 20 h. After cooling, the precipitate is filtered, concentrated by evaporation, the residue dissolved in ethyl acetate, the solution washed three times with a In sodium hydroxide solution, then with saturated sodium chloride solution, dried with magnesium sulphate and concentrated by evaporation under vacuum. After recrystallisation from diethylether, 1-(2-benzyl-4-ch1orophenoxy)-propan-2-one is obtained as a white powder with a melting point of 65-6C. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | With hydrogenchloride; potassium nitrate; sodium nitrite; In diethyl ether; water; for 2h; | To a mixture of 2-phenylmethyl-3-chlorophenol (5.00 g, 22.9 mmol) in Et2O (20 mL) and 6N HCl (50 mL), KNO3 (2.30 g, 22.9 mmol) and NaNO2 (20 mg, catalytic) were added sequentially. The resulting mixture was stirred for 2 hours, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure to give 99 (6.0 g, 100%). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 72% | With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20 - 80℃; for 1h; | Powdered K2CO3 (2.07 g, 15.0 mmol) is added to a stirred solution of 2-benzyl-4- chlorophenol (2.19 g, 10.0 mmol) and 1,3-dibromopropane (3.05 mL, 30.0 mmol) in anhydrous DMF (20 mL) at ambient temperature under nitrogen. The mixture is heated at 80 C for 1 hour. At ambient temperature, EtOAc (100 ML) and water (150 mL) are added to the mixture. The organic layer is separated, dried over MGS04, filtered and concentrated. The crude product is chromatographed on silica (gradient 0-2% EtOAc in hexane) to give 2.45 g (7.21 mmol, 72% yield) of the title compound as a white solid. EIMS: m/z 338 (M+, 35C1, 79Br), 340 (M+, 37C1, 79BR OR 35C1, 8LBR), 342 (M+, 37Cl, 8LBR). |
[ 120-32-1 ]
[ 137886-82-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 56% | With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 - 20℃; for 12h; | Example 19 Preparation of 4'-chloro-2'-benzylphenyl 2,3,4,6-tetra-O-acetyl-5-thio-beta-D-glucopyranoside 2,3,4,6-Tetra-O-acetyl-5-thio-D-glucopyranose (200 mg, 0.549 mmol), 4-chloro-2-benzylphenol (601 mg, 2.75 mmol), triphenylphosphine (191 mg, 1.10 mmol) and toluene (1.6 mL) were mixed, and to the resulting mixture, diethyl azodicarboxylate (40% in toluene, 0.48 mL, 1.10 mmol) was then slowly added dropwise in ice. After stirring at room temperature for 12 hours, the reaction mixture was concentrated and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 7:3) to give the titled compound (173 mg, 56%). 1H-NMR (300 MHz, CDCl3): delta 1.91 (s, 3H), 2.01 (s, 3H), 2.05 (s, 3H), 2.06 (s, 3H), 3.28 (m, 1H), 3.88 (s, 2H), 4.14 (dd, J = 3.7, 12.0Hz, 1H), 4.30 (dd, J = 5.3, 12.0Hz, 1H), 5.16 (dd, J = 8.8, 9.5Hz, 1H), 5.31 (d, J = 8.6Hz, 1H), 5.39 (dd, J = 9.5, 10.3Hz, 1H), 5.60 (dd, J = 8.6, 8.8Hz, 1H), 7.03-7.35 (m, 8H). ESI m/z = 587, 589 (M+Na). mp 111.0-114.0C. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate;copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 120℃;Heating; | Example 8 3-f 4- [3- (2-Benzyl-4-chloro-phenoxy)-phenoxy]-2-methyl-phenyl}-propionic acid A solution of 3- [4- (3-bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester (0.1 g, 0.3 mmol), 2-benzyl-4-chloro-phenol (69 mg, 0.32 mmol), copper (I) chloride (14 mg, 0.14 mmol), 2,2, 6,6-tetramethyl-3, 5-heptanedione (0.01 mL, 0.07 mmol), and cesium carbonate (113 mg, 0.35 mmol) in NMP (3 mL) is heated to 120 C. The reaction is stirred overnight and cooled to rt. The reaction is then quenched with IN aqueous HCl and extracted with ethyl ether. The organic is washed with brine, dried over sodium sulfate, and filtered. The solvent is removed to afford the crude ester intermediate. The intermediate is treated with 5N NaOH (0.4 mL, 2.2 mmol) in MeOH (5 mL) and heated to reflux. The reaction is stirred at reflux for 2 hours and then cooled. The reaction is quenched with IN aqueous HCl to obtain pH=4. The aqueous layer is extracted with ethyl ether. The organic layer is washed with brine, dried over sodium sulfate, and filtered. The solvent is removed to afford the crude product. The crude is purified by prep HPLC to afford 63 mg (47%) of desired product NMR (400 MHz, CDCl3) ; MS (ES+) mlz mass calculated for C29H25ClO4 472, found 473 and 475 (M + 1 andM+3, 100%). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate; mercury; In butanone; | (A) 3-(2-Benzyl-4-chlorophenoxy)-1,2-epoxypropane A suspension containing 21.87 g of 2-benzyl-4-chlorophenol, 27.76 g of 1-chloro-2,3-epoxypropane and 27.64 g of potassium carbonate in 200 ml of butanone is refluxed for 12 hours. The inorganic salts formed are filtered off and drained. The solvent and excess 1-chloro-2,3-epoxypropane are evaporated off under vacuum and the residue is distilled at between 160 C. and 180 C. under 0.01 mm of mercury. The colorless oil obtained solidifies rapidly. Weight: 21.7 g Yield: 79% |
[ 80-05-7 ]


[ 112-34-5 ]
[ 120-32-1 ]
[ 148-18-5 ]| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 0.5 part of the sodium salt of diethyldithiocarbamate, 1.5 parts of a 30% liquid dispersion of 2,5-di-tert-butyl-hydroquinone, or 1.0 part of a 50% liquid vatting accelerator of the following composition: 20 parts of 4,4'-isopropylidene-bis(phenol), 15 parts of 2-benzyl-4-chlorophenol, 15 parts of N-(hydroxyethyl)-ethylenediamine, 5 parts of concentrated NaOH 36Be', and 45 parts of butyl diglycol. |
[ 100-39-0 ]
[ 106-48-9 ]
[ 1050575-40-0 ]
[ 120-32-1 ]
[ 7700-27-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 67% | General procedure: Diisopropyl azodicarboxylate (DIAD, 5.0 mmol) was added slowly to a solution of o- arylphenols (48 a-h) (4.6 mmol)la, 2a and triphenylphosphine (5.0 mmol) in THF (10.0 mL) at room temperature. After stirring the reaction mixture for 10 minutes, 2-bromoethanol (0.35' mL, 5.0 mmol) was added to it and the resulting mixture was stirred at room temperature for 24 h. After completion, the reaction mixture was concentrated under reduced pressure and purified by column chromatography (Si02, hexane/EtOAc 80:20) to give 49 a-h; 2-benzyl-l-(2-bromoethoxy)-4-chlorobenzene (49 a) (1.2 g, 67%) 1H NMR (500 MHz, CDC13) delta 7.15 (s, 1H), 7.14 (dd, J= 2.0, 8.1 Hz, 1H), 7.12 (dd, J= 2.1, 8.3 Hz, 1H), 7.04 (d, J= 7.9 Hz, 1H), 6.96 (d, J= 2.5 Hz, 1H), 6.76 (d, J= 2.1 Hz, 1H), 4.46 (t, J - 4.7 Hz, 2H), 4.03 (s, 2H), 3.60 (t, J= 4.7 Hz, 2H). 13C NMR (126 MHz, CDC13) delta 154.48, 136.07, 132.63, 130.31, 129.75, 129.20, 127.50, 127.02, 126.50, 116.02, 112.59, 68.23, 32.81, 29.01. |