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CAS No. : | 101495-18-5 | MDL No. : | MFCD03094990 |
Formula : | C8H5Cl2N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NIXGYRHZQFZCCV-UHFFFAOYSA-N |
M.W : | 186.04 | Pubchem ID : | 14419624 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
14 g | With copper dichloride; In dimethyl sulfoxide; at 120.0℃; for 1.0h; | In the reaction bottle,22 g of 4,6-dichloroindolecarboxylic acid was added to 150 mL of DMSO, and then 3 g of copper chloride was added.The reaction was heated at 120 C for 1 h,TLC monitors the reaction of the starting material completely, and the reaction solution is filtered, and then 200 mL of dichloromethane is added to extract the reaction solution three times.The organic phases were combined, washed with 200 mL of water and concentrated.Then in a mixture of acetone and n-hexane (V acetone: V-hexane = 3:1)Recrystallization from 100 mL gives 4,6-dichloroanthracene 14g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step a 4,6-Dichloroindole Dissolve 4,6-dichloro-indole-2-carboxylic acid (1.0g, 4.35mmol) in quinoline (25mL). Add copper powder (100mg) and heat to 220 C. for 3 hours. Pour the resulting black solution into cold concentrated hydrochloric acid (300mL) and extract into ethyl ether (500mL). Filter, wash with 1M hydrochloric acid (2*200mL), water (100mL) and dry (MgSO4). Evaporate the solvent in vacuo to give a brown oil (0.76g). Purify by silica gel chromatography (17% ethyl acetate/hexane) to give the title compound as an amber oil (0.66g, 81%). 1 H NMR (CDCl3 /TMS): 6.56-6.59 ppm (1H, m), 7.10-7.13 ppm (2H, m), 7.16-7.18 ppm (1H, m). 13 C NMR (CDCl3), ppm: 101.48, 110.16, 120.24, 125.77, 125.94, 126.54, 122.79, 106.54. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; chloroform; acetone; | Step b Ethyl 2,-(hydroxyimino)-3-(4,6-dichloro-3-indolyl)propanoate Mix <strong>[101495-18-5]4,6-dichloroindole</strong> (5.90g, 31.72mmol), potassium carbonate (1.81g, 47.6mmol) and anhydrous methylene chloride (200mL). Stir and add a solution of ethyl 3-bromo-2-hydroxyiminopropanoate (7.00g, 33.31mmol) in methylene chloride (75mL). Stir under a nitrogen atmosphere for 48 hours. Take the solution up in methylene chloride (100mL) and wash with water (300mL), saturated sodium hydrogen carbonate (200mL) and brine (100mL). Dry (MgSO4) and evaporate the solvent in vacuo to give a tan solid. Purify by silica gel chromatography (1 to 3% acetone in chloroform) to give the title compound as a yellow solid (7.00g, 99% based on consumed starting material). Recrystallize (diethyl ether/hexane) to give the tit le compound as white crystals (4.0g, 56%); mp 175-176 C. 1 H NMR (DMSO-d6 /TMS): 1.19 ppm (3H, t), 4.15 ppm (2H, q), 4.15 ppm (2H, s), 6.95 ppm (1H, s), 7.10 ppm (1H, d), 7.40 ppm (1H, d), 11.3 ppm (1H, bs), 12.35 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 60.0℃; for 3.0h; | 4,6-dichloro-lH-indole (1 eq) was dissolved in DMF, K2COj (3eq) and 2-(3~ bromopropyl)isoindoline-l,3-dione (1.1 eq) was added and the mixture stirred at 60 C for 3 h. Solvent was removed and extracted with DCM. The organic extract was washed with water, brine and dried over Ma2S04. The residue was purified via flash chromatography on silica gel to obtain 2-(3-(4,6-dich3oro- lH-indoi-l-yr)propyi)isoindoline- .l,3-dione. |