Structure of 13001-29-1
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 13001-29-1 |
Formula : | C8H6Cl4O |
M.W : | 259.95 |
SMILES Code : | ClCCOC1=C(Cl)C=C(Cl)C=C1Cl |
MDL No. : | MFCD10566405 |
Boiling Point : | No data available |
InChI Key : | YNJGVSWHTYTTDC-UHFFFAOYSA-N |
Pubchem ID : | 11276959 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
98% | With thionyl chloride; In tetrachloromethane; water; | EXAMPLE 3 Preparation of 2-(2,4,6-trichlorophenoxy)-ethyl chloride Into a three-necked, round-bottom flask fitted with a stirrer, thermometer, reflux condenser and dropping funnel was added 250 g of 96% 2-(2,4,6-trichlorophenoxy) ethanol, 250 ml carbon tetrachloride and 4 g of benzyl-trimethyl-ammonium chloride. The mixture was heated to 55 C. and 146 g thionyl chloride was added dropwise over 1.5 hours. After the addition of the thionyl chloride the temperature of the reaction was slowly raised to 80 C. for a total reaction tme of 2.5 to 3 hours. The end of the reaction was determined by GLC. The mixture was cooled to 60 C. and water slowly added to decompose the excess thionyl chloride. The phases were separated and the organic phase was washed with a 10% sodium hydroxide solution until it reached a pH of 7. After an additional separation of the phases the organic phase was washed again with water. After a further separation of phases, the carbon tetrachloride was distilled off to yield an oil which slowly crystallized to form 257 g of 2-(2,4,6-trichlorophenoxy)-ethyl chloride in a purity of 96%-98% and yield of 98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With chlorine; acetic acid; urea; In water; | EXAMPLE 3 Preparation of 2-(2,4,6-trichlorophenoxy)-ethyl chloride Into a three-necked 250 ml flask fitted with a stirrer, thermometer and a gas bubbler, were added 20 g 2-phenoxy-ethyl chloride, 60 g acetic acid and 2 g urea. The mixture was cooled while stirring to 5 C. and the addition of chlorine gas was initiated. As the chlorination proceeded, the temperature of the reaction mixture was slowly raised, so that the third stage of chlorination took place at a temperature of 40 C. The overall reaction time was 6.5 hours. At the end of the reaction water was added, the organic phase separated and washed with water, then with sodium bisulfite solution, then with additional water. This afforded 28 g of 2-(2,4,6-trichlorophenoxy)-ethyl chloride in 80% yield. When exactly the same reaction was run with an overall reaction time of only 4.5 hours, a yield of only 74% was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.5% | at 110 - 125℃; under 4500.45 - 5625.56 Torr; for 5.0h;Sealed tube; Alkaline conditions; Inert atmosphere; Large scale; | In the S1 etherification kettle 3000L, 99% of 2,4,6-trichlorophenol (600 kg), 1200 kg of dichloroethane, and 30% of a liquid alkali of 500 kg were added, and nitrogen gas was substituted three times, stirring was started, and sealing heating was performed. The control temperature was 120-125 C, the pressure was 0.60-0.75 MPa, the reaction was carried out for 5.0 hours, and the sample was analyzed.After the reaction is passed, the temperature is cooled to 60 C, the stirring is stopped, and the mixture is allowed to stand for 1.0 hour. After the lower aqueous layer is separated, the material is transferred to a vacuum distillation still to remove the solvent, and the vacuum of the control kettle is at -0.095 to -0.098 MPa at the end of the distillation. When the solvent condensate flows out, the distillation is completed under reduced pressure, the heating is stopped, the vacuum is broken to normal pressure, and the barrel is metered to obtain the S1 intermediate (2,4,6-trichlorophenoxyethyl chloride), and the HPLC content is 98.0%. The rate is 91.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.5% | at 90 - 95℃; under 3000.3 - 3375.34 Torr; for 12.0h;Inert atmosphere; Autoclave; Large scale; | In the S2 amination kettle 3000L,S1 intermediate and 1200 kg of propylamine were added, and the mixture was replaced with nitrogen three times, stirring was started, and the temperature was raised by heating. The temperature in the control kettle is 90-95 C, the pressure is 0.40-0.45 MPa, the heat preservation reaction is 12.0 hours, and the sample is analyzed;After the reaction is passed, the temperature is lowered to normal temperature, the material is transferred to a treatment tank, the caustic soda is added, and the propylamine is heated and distilled until the distillation is completed without the propylamine being distilled off.Cool to room temperature, add water, stir for 1.0 hour, dissolve inorganic salt, etc., add 1200 kg of extractant xylene, stir for 1.0 hour, then let stand for 1.0 hour, separate the lower aqueous layer, collect the organic layer, and obtain S2 intermediate xylene solution.(N-(2,4,6-Trichlorophenoxyethyl)propylamine) was directly used in the next synthesis reaction, and the yield of S2 was 92.5%. |
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