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CAS No. : | 35112-28-8 | MDL No. : | MFCD00085117 |
Formula : | C8H6Cl2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VCRWILYAWSRHBN-UHFFFAOYSA-N |
M.W : | 205.04 | Pubchem ID : | 37055 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.74 |
TPSA : | 26.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.41 cm/s |
Log Po/w (iLOGP) : | 2.35 |
Log Po/w (XLOGP3) : | 3.01 |
Log Po/w (WLOGP) : | 2.78 |
Log Po/w (MLOGP) : | 3.09 |
Log Po/w (SILICOS-IT) : | 2.97 |
Consensus Log Po/w : | 2.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.25 |
Solubility : | 0.116 mg/ml ; 0.000568 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.23 |
Solubility : | 0.122 mg/ml ; 0.000593 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.71 |
Solubility : | 0.0398 mg/ml ; 0.000194 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.52 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-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 |
---|---|---|
Preparation 1.2 2-(4-Chlorophenyl)l-1(2,4-dichlorophenyl)ethanone 417 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to -60 C., under a nitrogen atmosphere, 350 ml of THF are added, followed by dropwise addition of a solution of 57 g of 4-chlorophenylacetic acid in 70 ml of THF and the mixture is stirred for 2 hours while allowing the temperature to rise to -40 C. The reaction mixture is cooled to -60 C., 65.3 g of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> are added dropwise and the mixture is stirred while allowing the temperature to rise to 0 C. The reaction mixture is poured into a mixture of ice/1 liter of 2N HCl and extracted with ether, the organic phase is dried over Na2SO4 and the solvent is concentrated under vacuum to a volume of 150 ml. The remaining solution is poured into 300 ml of pentane and the crystalline product formed is filtered off by suction. 60 g of the expected compound are obtained. | ||
420 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to -60 C., under a nitrogen atmosphere, 350 ml of THF are added, and then, dropwise, a solution of 57.6 g of 4-chlorophenylacetic acid in 70 ml of THF and the mixture is kept stirred for 1 hour at -60 C. 66 g of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> are then added, dropwise and at -60 C., the mixture is kept stirred for 40 minutes at -60 C. and then the temperature is allowed to rise to 0 C. The reaction mixture is poured over an ice/1 liter of 2N HCl mixture, extracted with ether, the organic phase is washed with a saturated NaHCO3 solution, with water, the organic phase is dried over Na2SO4, the solvent is concentrated under vacuum to a volume of 150 ml, 200 ml of pentane are added and the crystallized product formed is drained. 60 g of the expected compound are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation 1.2; 2-(4-Bromophenyl)-1-(2,4-dichlorophenyl)ethanone; 436 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to -60 C. under a nitrogen atmosphere, 400 ml of THF are added, a solution of 75 g of 4-bromophenylacetic acid in 100 ml of THF is then added dropwise and the mixture is left stirring at -70 C. for 1 hour 30 minutes. 67.9 g of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> are subsequently added dropwise, the mixture is left stirring for 30 minutes and then the temperature is allowed to rise to 5 C. The reaction mixture is poured onto an ice/1 liter of 2N HCl mixture and extracted with ether, the organic phase is washed with a saturated NaHCO3 solution and with water and dried over Na2SO4, the solvent is evaporated under vacuum to a volume of 200 ml, pentane is added and the crystalline product formed is filtered off. 80 g of the expected compound are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation 1.1; 2-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)ethanone; 420 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to -60 C. under a nitrogen atmosphere, 350 ml of THF are added, then, dropwise, a solution of 57.6 g of 4-chlorophenylacetic acid in 70 ml of THF is added and the mixture is left stirring at -60 C. for one hour. 66 g of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> are subsequently added dropwise at -60 C., the mixture is left stirring at -60 C. for 40 minutes and then the temperature is allowed to rise to 0 C. The reaction mixture is poured onto an ice/1 liter of 2N HCl mixture and extracted with ether, the organic phase is dried over Na2SO4, the solvent is concentrated under vacuum to a volume of 150 ml, 200 ml of pentane are added and the crystalline product formed is filtered off. 60 g of the expected compound are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation 1.3; 1-(2,4-Dichlorophenyl)-2-(4-methoxyphenyl)ethanone; 413 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to -65 C. under a nitrogen atmosphere, 300 ml of THF are added, a solution of 55 g of 4-methoxyphenylacetic acid in 70 ml of THF is then added dropwise and the mixture is left stirring for 3 hours at a temperature of less than -45 C. 64.5 g of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> are subsequently added dropwise and the mixture is left stirring while allowing the temperature to rise to 0 C. The reaction mixture is poured onto an ice/1 liter of 2N HCl mixture and extracted with ether, the organic phase is washed with a saturated NaHCO3 solution and dried over Na2SO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with heptane and then with the heptane/AcOEt mixture up to (90/10; v/v). 29 g of the expected compound are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The other compounds of Example 3 were prepared by essentially the same procedure using the corresponding carboxamide and acyl hydrazide. Acetonitrile was used as solvent in the preparation of 3-2. Compound [3-19] was isolated as a byproduct in the synthesis of 3-18. The methyl amides were prepared from their corresponding methyl esters and [METHYLAMINE] using well established protocols. The other amides were conveniently prepared from commercially available carboxylic acids and amines using 1- (dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride as the reagent and published procedures. Preparation of the acyl hydrazides was described in Procedures 3A, 3B, 3C and 3D. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In tetrahydrofuran; hexane; | Step A 2-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)ethanone A 5 L round bottom flask equipped with an addition funnel, N2 inlet, thermometer and a mechanical stirrer was charged with 387 mL of 1M sodium bis-trimethylsilylamide in THF and cooled to -60 C. A solution of 230 g (1.35 mol) of 4-chlorophenylacetic acid in 300 mL of THF was added keeping the temperature below -40 C. After stirring the mixture for 90 min at -70 C., 264 g (1.29 mol) of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> was added over 20 min. The solution was stirred for 40 min at -70 C., the cooling bath was removed and the mixture was allowed to warm to 0 C. Reaction was quenched by pouring into 4 L of 2N HCl and ice and extracted with ether. Each ether layer was washed with saturated NaHCO3, brine, dried with MgSO4 and filtered through a 2" plug of silica gel. The filtrate was concentrated to ca. 1 lit of a slushy liquid which was diluted with 1 L of hexane and cooled in a refrigerator. The solid formed was filtered, washed with hexane and dried. A second crop was isolated by concentrating the mother liquors. The two crops of crystals were combined. 1H NMR: (500 MHz, CDCl3): delta 4.21 (s, 2H), 7.2-7.5 (m, 7H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sulfuric acid; In methanol; | (1) Methyl 2,4-dichlorobenzoate The synthesis was carried out according to the method of Example 7-(1). 2,4-Dichlorobenzoic acid (25.0 g), 1,2-dichloroethane (50 ml), methanol (40 ml), concentrated sulfuric acid (2.0 ml) were used as reagents to give 24.5 g of a colorless transparent liquid (yield 91%). IR (KBr): 3080, 2910, 1720, 1580, 1545 cm-1 1 H-NMR (CDCl3) delta: 3.87(3H, s), 7.57(1H, dd, J=8.4, 2.0 Hz), 7.78(1H, d, J=2.0 Hz), 7.86(1H, d, J=8.4 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 6 The reaction was run as above with 1.73 g of 2,4-dichlorobenzoic anhydride and 0.21 g of trioxane. After 18 hours the reaction was stopped and the product isolated as above to give 1.56 g of a mixture of the bis-2,4-dichlorobenzoyloxy methane and bis-2,4-dichlorobenzoyloxymethyl ether. The ether obtained by fractional crystallization from chloroform-hexane gave 0.28 g (19%) of needles, mp 80.5-81.5 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
from <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> and methyl 2,4-dichlorobenzoate there is obtained 2',4'-dichloro-2-(2-pyrazinyl)-propiophenone as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In methanol; | (i) Methyl 2,4-Dichlorobenzoate 2,4-Dichlorobenzoic acid (50g: Aldrich) was refluxed with thionyl chloride (250ml) for 1 hour. The solution was filtered and evaporated to drynesn under reduced pressure. The resulting oil was added dropwise to dry methanol (200ml) with stirring at room temperature. After 1 hour the resulting solution was evaporated to dryness under reduced pressure and the residue taken up in ether. The organic phase was washed twice with water, charcoaled filtered and dried over magnesium sulphate. Yield 40g of a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2-(4-Bromophenyl)-1-(2,4-dichlorophenyl)ethanone 436 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF is cooled to -60 C., in a nitrogen atmosphere, 400 ml of THF is added then, dropwise, a solution of 75 g of 4-bromophenylacetic acid in 100 ml of THF and it is stirred for 1 h 30 min at -70 C. Then 67.9 g of methyl-2,4-dichlorobenzoate is added dropwise, stirred for 30 minutes, then the temperature is allowed to rise to 5 C. The reaction mixture is poured onto a mixture of ice/1 liter of 2N HCl, extracted with ether, the organic phase is washed with a saturated NaHCO3 solution, then with water, dried over Na2SO4 and the solvent is evaporated under vacuum to a volume of 200 ml, pentane is added and the crystalline product that forms is dried. 80 g of the expected compound is obtained. | ||
Preparation 1.1 2-(4-Bromophenyl)-1-(2,4-dichlorophenyl)ethanone 436 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to -60 C., under a nitrogen atmosphere, 400 ml of THF are added, followed by dropwise addition of a solution of 75 g of 4-bromophenylacetic acid in 100 ml of THF, and the mixture is stirred for 1 hour 30 minutes at -70 C. 67.9 g of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> are then added dropwise and the mixture is stirred for 30 minutes and then allowed to warm to 5 C. The reaction mixture is poured into a mixture of ice/1 liter of 2N HCl and extracted with ether, the organic phase is washed with saturated NaHCO3 solution and with water, and dried over Na2SO4, the solvent is evaporated off under vacuum to a volume of 200 ml, pentane is added and the crystalline product formed is filtered off by suction. 80 g of the expected compound are obtained. | ||
436 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to -60 C., under a nitrogen atmosphere, 400 ml of THF are added, followed dropwise by a solution of 75 g of 4-bromophenylacetic acid in 100 ml of THF and the medium is left for 1 hour 30 minutes with stirring at -70 C. 67.9 g of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> are then added dropwise, the medium is left for 30 minutes, with stirring, and then the temperature is allowed to rise to 5 C. The reaction mixture is poured over an ice/1 liter of 2N HCl mixture, extracted with ether, the organic phase is washed with a saturated NaHCO3 solution, with water, dried over Na2SO4 and the solvent is evaporated under vacuum to a volume of 200 ml, pentane is added and the crystallized product formed is drained. 80 g of the expected compound are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; at -20 - 20℃; for 17.0833h; | Methyl 2,4-diethylbenzoate. To a mixture of Fe(acac)3 (0.34 g, 0.96 mmol), methyl 2,4-dichlorobenzoate (4.0 g, 19.6 mmol), and N-methyl-2-pyrrolidinone (8 mL) in THF (100 mL) at -20 C. under nitrogen was added a tetrahydrofuran (THF) solution (1.0 M) of ethylmagnesium bromide (40.0 mL, 40.0 mmol) over a period of 5 min. The resulting mixture was stirred while gradually warming to ambient temperature. Stirring was continued for an additional 17 h. The reaction mixture was partitioned between water and dichloromethane. The organic layer was separated, washed with brine, dried (MgSO4), and pumped to dryness under reduced pressure. The brown residue was purified by column chromatography (SiO2, 20% EtOAc/heptane) to give 1.2 g of the desired product as a clear oil (yield of 32%), along with 1.1 g of methyl 4-ethylbenzoate. 1H NMR (300 MHz, DMSO-d6) delta 1.15 (t, 3H), 1.20 (t, 3H), 2.66 (q, 2H), 2.92 (q, 2H), 3.82 (s, 3H), 7.15 (d, 1H), 7.23 (s, 1H), 7.76 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With aluminium(III) chloride hexahydrate; urea hydrogen peroxide adduct; at 60℃;Green chemistry; | General procedure: A mixture of aldehyde (1.0 mmol), aluminum chloride hexahydrate (10 mol %), and urea hydrogen peroxide (5.0 mmol) was stirred in methyl alcohol (4.0 mL) at 60C for 8-12 h. After cooling the mixture to room temperature the product was extracted into ethyl acetate (3 × 20 mL), washed with water and dried over sodium sulfate. The combined ether extracts were concentrated under reduced pressure and the crude product was purified by flash column chromatography (ethyl acetate/nhexane= 1:4, v/v) to give the desired methyl ester. |
80% | With urea hydrogen peroxide adduct; p-toluenesulfonyl chloride; at 60℃; for 8h; | General procedure: A general experimental procedure for the esterification ofaldehydes is as follows: An aldehyde (1 mmol) was reacted with urea hydrogen peroxide (5 mmol) and p-toluenesulfonylchloride (1 mmol) in 3 mL of methanol at 60C for 6-8 h.After completion of the reaction, the solvent was removed invacuo and the residue was dissolved in ethyl acetate (20 ml),washed with saturated sodium bicarbonate solution (20 ml)and dried over anhydrous sodium sulfate. After removal ofsolvent, the crude product was purified by column chromatography(230-400 mesh silica gel, n-hexane/ethyl acetate =1/4). Purification of the product with silica gel flash columnchromatography with ethyl acetate: hexane (1:4) eluentyielded the pure methyl carboxylic ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
413 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to -65 C., under a nitrogen atmosphere, 300 ml of THF are added, followed dropwise by a solution of 55 g of 4-methoxyphenylacetic acid in 70 ml of THF and the mixture is kept stirred for 3 hours at a temperature of less than -45 C. 64.5 g of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> are then added dropwise and the mixture is kept stirred while the temperature is allowed to rise to 0 C. The reaction mixture is poured over an ice/1 liter 2N HCl mixture, extracted with ether, the organic phase is washed with a saturated NaHCO3 solution, dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluted with heptane and then with the heptane/AcOEt mixture to (90/10; v/v). 29 g of the expected compound are obtained. | ||
1A) 1-(2,4-Dichlorophenyl)-2-(4-methoxyphenyl)ethanone 367 ml of NaHMDS (2M in THF) are added to 250 ml of THF and the mixture is cooled to -70 C. 54 g of (4-methoxyphenyl)acetic acid are then added; the mixture is left stirring for 2 hours and then 49 g of <strong>[35112-28-8]methyl 2,4-dichlorobenzoate</strong> are added. The reaction mixture is allowed to return to 10 C. and poured onto 2 litres of ice-cold HCl (2N), and the product is extracted with ether. After drying with a saturated sodium bicarbonate solution and then a saturated NaCl solution, drying the organic phase and evaporating, the product crystallizes from heptane; 32 g of the expected compound are obtained. |
Tags: 35112-28-8 synthesis path| 35112-28-8 SDS| 35112-28-8 COA| 35112-28-8 purity| 35112-28-8 application| 35112-28-8 NMR| 35112-28-8 COA| 35112-28-8 structure
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P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
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 |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
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 |
Sorry,this product has been discontinued.
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