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[ CAS No. 117528-58-2 ] {[proInfo.proName]}

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Chemical Structure| 117528-58-2
Chemical Structure| 117528-58-2
Structure of 117528-58-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 117528-58-2 ]

CAS No. :117528-58-2 MDL No. :MFCD18801150
Formula : C8H2Cl2FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PAJAHSZQWFSIFX-UHFFFAOYSA-N
M.W : 234.01 Pubchem ID :10900541
Synonyms :

Calculated chemistry of [ 117528-58-2 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.09
TPSA : 61.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.07
Log Po/w (XLOGP3) : 2.52
Log Po/w (WLOGP) : 3.12
Log Po/w (MLOGP) : 2.54
Log Po/w (SILICOS-IT) : 2.94
Consensus Log Po/w : 2.44

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.13
Solubility : 0.174 mg/ml ; 0.000742 mol/l
Class : Soluble
Log S (Ali) : -3.45
Solubility : 0.0832 mg/ml ; 0.000356 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.38
Solubility : 0.0985 mg/ml ; 0.000421 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 117528-58-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 117528-58-2 ]

* 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.

  • Downstream synthetic route of [ 117528-58-2 ]

[ 117528-58-2 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 214774-58-0 ]
  • [ 117528-58-2 ]
YieldReaction ConditionsOperation in experiment
With formic acid; hydroxylamine hydrochloride 8 3-Cyano2,4-dichloro-5-fluorobenzoic acid EXAMPLE 8 3-Cyano2,4-dichloro-5-fluorobenzoic acid 162 g of hydroxylamine hydrochloride were introduced into 2000 ml of formic acid (technical-grade, 85% strength). At 95° C., 950 g of 2,4-dichloro-5-fluoro-3-formylbenzoic acid (moistened with sulphuric acid, 42% strength) were introduced. As a result, the mixture foamed briefly and then a clear solution was immediately obtained. The mixture was then stirred for 4 hours at from 100 to 105° C. (reflux). After the mixture had been cooled to room temperature, it was poured onto water, thoroughly stirred, filtered with suction and dried. This gave 364 g (90.3% of theory) of 3-cyano-2,4-dichloro-5-fluorobenzoic acid with a content, according to GC, of 97.7%.
  • 2
  • [ 117528-58-2 ]
  • [ 117528-59-3 ]
YieldReaction ConditionsOperation in experiment
With pyridine; thionyl chloride 9 3-Cyano-2,4-dichloro-5-fluorobenzoyl chloride EXAMPLE 9 3-Cyano-2,4-dichloro-5-fluorobenzoyl chloride 4100 ml of thionyl chloride and 41 ml of pyridine were introduced into a stirred apparatus fitted with metering device and gas outlet leading to a scrubber via a reflux condenser, and, at 20° C., 2050 g of 3-cyano-2,4-dichloro-5-fluorobenzoic acid (99.5% strength) were introduced at the rate of hydrogen chloride/sulphur dioxide evolution. At the end of the addition, the mixture was heated to reflux until the evolution of gas ceased. The mixture was then distilled. In the boiling range from 142 to 145° C./10 mbar, 2150 g (95.7% of theory) of 3-cyano-2,4-dichloro-5-fluorobenzoyl chloride were obtained (content according to GC: 98.0%).
With thionyl chloride In toluene for 3h; Reflux;
  • 4
  • [ 466639-56-5 ]
  • [ 124-38-9 ]
  • [ 117528-58-2 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 2,6-dichloro-3-fluoro-5-bromobenzonitrile With isopropylmagnesium chloride In tetrahydrofuran at -80 - -70℃; for 1h; Stage #2: carbon dioxide With water In tetrahydrofuran at 20℃; 9-13; 1-2 Example 9 In a 500 ml dry reaction bottle, add 25 g of 2,6-dichloro-3-fluoro-5-bromobenzonitrile and 150 g of tetrahydrofuran.Stir and cool to -70 to -80°C,Slowly add 51 ml of a solution of 2 mol per liter of isopropylmagnesium chloride in tetrahydrofuran. After the addition is complete,The reaction was continued at -70 to -80°C for 1 hour.Slowly feed the system with carbon dioxide gas, and naturally return to room temperature, stop the carbon dioxide flow, add 150 grams of water,Stir for a while, let stand, separate the organic phase, adjust the pH of the aqueous phase to 1 with hydrochloric acid, extract three times with ethyl acetate, combine the ethyl acetate layers, dry and concentrate,20.2 g of 2,4-dichloro-3-cyano-5-fluorobenzoic acid was obtained,The yield was 93% and the purity was 99.4%.
88.6% Stage #1: 2,6-dichloro-3-fluoro-5-bromobenzonitrile With sec.-butyllithium In tetrahydrofuran; 2-methyltetrahydrofuran at -80 - -70℃; for 1h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; 2-methyltetrahydrofuran at -78 - 20℃; for 1h; 2.1; 2.2; 2.3; 2.4 (1) In a dry reaction apparatus, 100 mL of 2-methyltetrahydrofuran and 13.5 g of 50 mmol of 2,6-dichloro-3-cyano-5-fluorobromobenzene were added, and nitrogen gas was passed below the liquid level.Cool down to -80 ~ -70 ° C;(2) slowly adding a 1.3 M solution of sec-butyllithium in tetrahydrofuran (58 mL, 75 mmoL) to the solution of the step (1), and after stirring, the reaction was stirred at -80 to -70 ° C for 1 hour;(3) introducing carbon dioxide gas into the reaction system of the step (2) for half an hour,The reaction was carried out at -78 ° C for half an hour, and gradually increased to room temperature after completion of the reaction.Release carbon dioxide and nitrogen, and quench the reaction with ice water;(4) adjusting the pH of the reaction system (3) to 1 to 3 with 2N diluted hydrochloric acid,The separated water layer is discarded, and the organic layer is further adjusted to pH 11 to 12 with 2N sodium hydroxide;The organic layer was separated and discarded, and 200 mL of isobutanol was added to the aqueous layer.The pH was adjusted to 1-3 with 6N hydrochloric acid; the aqueous layer was separated and the organic layer was washed with water.Static layering, organic layer,It was evaporated to dryness under reduced pressure at 60 ° C to give a pale yellow powder solid product.
60% Stage #1: 2,6-dichloro-3-fluoro-5-bromobenzonitrile With 2-methylpropylmagnesium chloride In tetrahydrofuran at -50℃; for 1h; Stage #2: carbon dioxide In tetrahydrofuran at -5℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; water
  • 5
  • [ 117528-58-2 ]
  • [ 117528-63-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thionyl chloride; triethylamine / dichloromethane / 35 - 40 °C 1.2: 12 h / -5 - 20 °C 2.1: acetic acid / 12 h / 10 - 20 °C
  • 6
  • [ 117528-58-2 ]
  • [ 1629778-38-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: thionyl chloride; triethylamine / dichloromethane / 35 - 40 °C 1.2: 12 h / -5 - 20 °C 2.1: acetic acid / 12 h / 10 - 20 °C 3.1: triethylamine / acetonitrile / 75 - 80 °C
  • 7
  • [ 117528-58-2 ]
  • [ 117528-65-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: thionyl chloride; triethylamine / dichloromethane / 35 - 40 °C 1.2: 12 h / -5 - 20 °C 2.1: acetic acid / 12 h / 10 - 20 °C 3.1: triethylamine / acetonitrile / 75 - 80 °C 4.1: sulfuric acid; acetic acid / water / 3 h / Reflux
  • 8
  • [ 117528-58-2 ]
  • [ 195532-12-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: thionyl chloride; triethylamine / dichloromethane / 35 - 40 °C 1.2: 12 h / -5 - 20 °C 2.1: acetic acid / 12 h / 10 - 20 °C 3.1: triethylamine / acetonitrile / 75 - 80 °C 4.1: sulfuric acid; acetic acid / water / 3 h / Reflux 5.1: dichloromethane / 70 h / 20 °C
  • 9
  • [ 117528-58-2 ]
  • [ 924-99-2 ]
  • [ 1159908-25-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,4-dichloro-3-cyano-5-fluorobenzoic acid With thionyl chloride; triethylamine In dichloromethane at 35 - 40℃; Stage #2: ethyl 3-(dimethylamino)acrylate In dichloromethane at -5 - 20℃; for 12h; 1.1 2,4-Dichloro-3-cyano-5-fluorobenzoic acid 24 g was put into the reaction flask.Add dichloromethane 240mL,28.8 g of thionyl chloride was added dropwise;After stirring for 5 minutes,Add triethylamine 2mL,Stir and slowly warm up to 35 ~ 40 °C, reflux 3 ~ 5 hours;After the reaction is completed, cool down to -5 to -10°C.15.2 g of triethylamine and21.5 g of a mixture of ethyl 3-dimethylaminoacrylate,After the drop was warmed to room temperature, the reaction was continued for 12 hours.TLC detected the reaction of compound 7; the reaction was complete;The ice bath was cooled, and 24 mL of acetic acid was added below 10°C.Stir for 5 minutes and add 9 g of 1-aminocyclopropane.The reaction was continued at room temperature for 12 hours, and the TLC reaction mixture of compound 6 was completed; Add 100mL of water, 6N hydrochloric acid to adjust the pH of 5.5 to 6.5, and stand for layering the organic layer.Concentrate methylene chloride below 40°CAdd ethanol 100ml crystal;Vacuum filtration wet product;Dry at 50-60°C for 8 hours under reduced pressure,The white powdery solid received is the compound of formula 5 2-(2,4-dichloro-3-cyano-5-fluorobenzoyl)-3-cyclopropylaminoacrylic acid ethyl ester, dry weight 32.4 g, Yield 85%.
  • 10
  • [ 136514-16-4 ]
  • [ 124-38-9 ]
  • [ 117528-58-2 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 2,6-dichloro-3-fluoro-benzonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -80 - -70℃; for 1h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -80 - -60℃; for 0.5h; 1.1; 1.2; 1.3; 1.4 (1) In a dry reaction apparatus, add 100 mL of tetrahydrofuran and 20.2 g of diisopropylamine, pass nitrogen gas below the liquid level, cool down to -80 to -70 ° C, and add 80 mL of 2.5 M n-butyllithium in n-hexane solution. , drip, heat for half an hour;(2) Dissolving 19 g of 2,6-dichloro-3-fluorobenzonitrile in 40 mL of tetrahydrofuran, maintaining the temperature at -80 to -70 ° C, dropping into the solution of the step (1), dropping, and keeping the temperature for one hour;(3) Maintaining the temperature at -80 to -60 ° C, slowly introducing carbon dioxide gas into the reaction system of step (2), reacting for 30 minutes until the reaction is completed, gradually increasing to room temperature, releasing carbon dioxide and nitrogen, and quenching the reaction with ice water. ;(4) The pH of the reaction system was adjusted to 1 to 3 with 6N diluted hydrochloric acid, 200 mL of ethyl acetate was added, and the layer was allowed to stand for separation. The separated aqueous layer was discarded, and the separated organic layer was washed with water. The organic layer obtained after static stratification was evaporated to dryness under reduced pressure at 60 ° C to give a pale yellow powder solid product.
  • 11
  • [ 178813-76-8 ]
  • [ 117528-58-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-bromoacetamide; sulfuric acid / 25 h / 30 - 35 °C 2.1: trichlorophosphate / chlorobenzene / 10 h / 20 °C / Reflux 3.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -80 - -70 °C 3.2: 20 °C
  • 12
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
  • [ 106809-14-7 ]
  • [ 117528-58-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,4-dichloro-5-fluoro-3-nitro-benzoic acid With palladium on activated charcoal; hydrogen In ethanol at 60℃; Stage #2: With sulfuric acid at 100℃; for 2h; Stage #3: sodium cyanide; copper (I) cyanide Further stages; 1-3 Example 1 Reduction: Add 1000 grams of industrial ethanol into the hydrogenation kettle, add 400 grams of 2,4-dichloro-3-nitro-5-fluorobenzoic acid, add 10 grams of Pd/c catalyst, and heat up to 60 ° C after nitrogen replacement, and pass The hydrogen reaction is completed when the hydrogen is not consumed, and the remaining 0.5% of the sampling raw material is qualified; after filtering out the catalyst, it is distilled to 90 until there is no flow liquid, and the ethanol is recovered;Salt formation, diazotization: add 400 grams of 98% sulfuric acid to the reactor, add 100 grams of aminocarboxylic acids, heat up to 100 ° C, keep stirring for 2 hours, then cool to 0 ± 2 ° C, configure sodium nitrite solution (water 150 grams, 30 grams of sodium nitrite) and cooled to 0 ° C, dripped under the heat preservation state, then kept warm for 2 hours, cooled to -5 ° C, added 300 grams of water, and kept the temperature;Cyanation: add 450 grams of water into the cyanation kettle, open the absorption valve on the kettle, add 125 grams of NaCN and 75 grams of CuCN, start the cyanation kettle stirring, the temperature of the kettle will automatically rise to 45 , and the temperature will drop after stirring for 30 minutes To -2°C, open the diazotization kettle dripping valve, maintain the kettle temperature at 0°C, drop the diazonium salt, and keep the cyanide kettle temperature at 0°C for half an hour. After suction filtration, a filter cake is obtained;Alkali-soluble: first add 600 grams of water to the alkali-soluble kettle, then add 80 grams of Na2CO3, start stirring for 10 minutes, add the filter cake to the kettle, stir for 30 minutes, measure the pH value, if the pH is less than 8.5, add 10% Na2CO3 , until PH=8.5-9, carry out suction filtration, and the filtrate enters the acidification kettle;Acidification: 30% sulfuric acid is prepared in the acidification dropping kettle in advance, and H2SO4 is slowly added dropwise to the acidification kettle. When the pH in the kettle is 1, the acid dripping is stopped, and the temperature of the kettle is kept at 10 °C. Then the material is suction filtered, and the filter cake is dried. , vacuum drying, -0.1MPa, temperature 80 , the product content is 99%
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