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CAS No. : | 4170-90-5 | MDL No. : | MFCD00014422 |
Formula : | C10H14O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LODDFDHPSIYCTK-UHFFFAOYSA-N |
M.W : | 150.22 | Pubchem ID : | 20139 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.47 |
TPSA : | 20.23 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) : | -5.7 cm/s |
Log Po/w (iLOGP) : | 2.33 |
Log Po/w (XLOGP3) : | 2.13 |
Log Po/w (WLOGP) : | 1.95 |
Log Po/w (MLOGP) : | 2.49 |
Log Po/w (SILICOS-IT) : | 3.09 |
Consensus Log Po/w : | 2.4 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.45 |
Solubility : | 0.532 mg/ml ; 0.00354 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.19 |
Solubility : | 0.978 mg/ml ; 0.00651 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.37 |
Solubility : | 0.0641 mg/ml ; 0.000427 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
100% | With thionyl chloride In dichloromethane at 0 - 20℃; for 1 h; | 2,4,6-trimethylbenzyl alcohol (150 mg, 1 .0 mmol) was dissolved in anh. DCM (4 mL). Thionyl chloride (87 μΙ_, 1 .2 mmol) was added slowly at 0 °C. The reaction mixture was stirred at RT. for 1 h. Removal of the solvent under reduced pressure gave the desired 2,4,6- trimethylbenzyl chloride (168 mg, 100 percent) as a white powder.1 H NMR (300 MHz, CDCI3) δ 2.29 (s, 3H), 2.42 (s, 6H), 4.68 (s, 2H), 6.89 (s, 2H). MS [M+H]+ 133. |
98% | With oxalyl dichloride In dichloromethane at 20℃; Reflux | General procedure: To 16 (0.6 g, 0.6 mmol) was added dichloromethane (5 mL) in a round-bottom flask. After 10 min, oxalyl chlorideor oxalyl bromide was added (0.6 mmol). The reaction mixture was magnetically stirred at room temperature. Uponcessation of gas evolution, 4 was added (0.5 mmol), and the reaction mixture was heated to reflux. After thereaction was complete according to TLC analysis, the mixture was cooled to room temperature and filtered. Thesolid on the funnel was washed with dichloromethane (3 × 10 mL), and the filtrate was concentrated under reducedpressure to afford the desired product 5 in an essentially pure state based on 1H and 13C NMR spectroscopicanalyses. |
94 %Spectr. | With chloro-trimethyl-silane In dichloromethane; water at 20℃; for 0.666667 h; | General procedure: In a flask was placed Na-Mont (30 mg), 1a (1 mmol, 0.18 g),TMSCl (2 mmol, 0.22 g, 0.25 mL), and CH2Cl2 (5 mL). The mixture was stirred at r.t. for 40 min. The solid material was filtered off, and the filtrate was concentrated. Compound 3a was isolated by Kugelrohr distillation under vacuum in 90percent yield as a colorless liquid.#10; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With Oxalyl bromide In dichloromethane at 20℃; Reflux | General procedure: To 16 (0.6 g, 0.6 mmol) was added dichloromethane (5 mL) in a round-bottom flask. After 10 min, oxalyl chlorideor oxalyl bromide was added (0.6 mmol). The reaction mixture was magnetically stirred at room temperature. Uponcessation of gas evolution, 4 was added (0.5 mmol), and the reaction mixture was heated to reflux. After thereaction was complete according to TLC analysis, the mixture was cooled to room temperature and filtered. Thesolid on the funnel was washed with dichloromethane (3 × 10 mL), and the filtrate was concentrated under reducedpressure to afford the desired product 5 in an essentially pure state based on 1H and 13C NMR spectroscopicanalyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16%Chromat. | With formaldehyd; tricarbonyl(eta4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; water; sodium carbonate; In dimethyl sulfoxide; at 120℃; for 24h;Inert atmosphere; Sealed tube; | General procedure: Knoelker iron complex 2a (3 mol %,12.6 mg), paraformaldehyde (300 mg, 10 mmol), and Na2CO3 (106 mg, 1 mmol,1.0 equiv) and a stirring bar were charged in a pressure tube and flushed withargon. DMSO (1.0 mL), degassed water (1.0 mL), and benzaldehyde (1 mmol)were added under an argon atmosphere to the pressure tube with a syringe.The pressure tube was placed in oil and heated at 120 C for 24 h, then cooledto room temperature. The reaction mixture was neutralized with HCl (1M) andstirred for 30 min. After extraction with EtOAc for 3 times, the combinedorganic layers were dried over MgSO4. The crude product was purified bycolumn chromatography (Heptane/EtOAc: 70:30). The reaction was cooled toroom temperature and hexadecane (100 lL) was added as a GC internalstandard. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride; In dichloromethane; at 0 - 20℃; for 1h; | <strong>[4170-90-5]2,4,6-trimethylbenzyl alcohol</strong> (150 mg, 1 .0 mmol) was dissolved in anh. DCM (4 mL). Thionyl chloride (87 muIota_, 1 .2 mmol) was added slowly at 0 C. The reaction mixture was stirred at RT. for 1 h. Removal of the solvent under reduced pressure gave the desired 2,4,6- trimethylbenzyl chloride (168 mg, 100 %) as a white powder.1 H NMR (300 MHz, CDCI3) delta 2.29 (s, 3H), 2.42 (s, 6H), 4.68 (s, 2H), 6.89 (s, 2H). MS [M+H]+ 133. |
98% | With oxalyl dichloride; In dichloromethane; at 20℃;Reflux; | General procedure: To 16 (0.6 g, 0.6 mmol) was added dichloromethane (5 mL) in a round-bottom flask. After 10 min, oxalyl chlorideor oxalyl bromide was added (0.6 mmol). The reaction mixture was magnetically stirred at room temperature. Uponcessation of gas evolution, 4 was added (0.5 mmol), and the reaction mixture was heated to reflux. After thereaction was complete according to TLC analysis, the mixture was cooled to room temperature and filtered. Thesolid on the funnel was washed with dichloromethane (3 × 10 mL), and the filtrate was concentrated under reducedpressure to afford the desired product 5 in an essentially pure state based on 1H and 13C NMR spectroscopicanalyses. |
94%Spectr. | With chloro-trimethyl-silane; In dichloromethane; water; at 20℃; for 0.666667h; | General procedure: In a flask was placed Na-Mont (30 mg), 1a (1 mmol, 0.18 g),TMSCl (2 mmol, 0.22 g, 0.25 mL), and CH2Cl2 (5 mL). The mixture was stirred at r.t. for 40 min. The solid material was filtered off, and the filtrate was concentrated. Compound 3a was isolated by Kugelrohr distillation under vacuum in 90% yield as a colorless liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With ammonium hydroxide; dihydrogen peroxide; In water; acetonitrile; at 30℃; for 3h; | General procedure: In a typical experiment, alcohol (10 mmol), aqueous NH3*H2O (30 mmol), FeCl4-IL-SiO2 (0.5 g), and CH3CN (10 mL) were added to a round-bottomed flask. Then, aqueous 30 % H2O2 (21 mmol) was gradually added into the reactor at room temperature. The obtained mixture was stirred at 30 C for appropriate time (Table 4). The reaction was monitored by TLC and GC. After completion of the reaction, the catalyst was recovered by filtration. Evaporation of the solvent under reduced pressure gave the crude product. Further purification was achieved by flash column chromatography on a silica gel (petroleum ether/ethyl acetate, 5:1) to give the desired product. Fresh substrates were then recharged to the recovered catalyst and then recycled under identical reaction conditions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With diethylene glycol dimethyl ether; at 70℃; for 0.5h;Sonication; | In a 10 mL round bottom flask, 0.75 g of <strong>[4170-90-5]2,4,6-trimethylbenzyl alcohol</strong> was added in sequence.2 g of diethylene glycol dimethyl ether, the resulting mixture was subjected to ultrasonic irradiation at 40 KHz/30 W/70 C for 30 minutes in an ultrasonic reaction apparatus. Diethylene glycol dimethyl ether was removed under reduced pressure, and recrystallized to give 0.76 g of 2,4,6-trimethylbenzoic acid, yield 93%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.62% | caesium carbonate; In 1,4-dioxane; for 4h;Heating / reflux; | A mixture of 1.50 g (0.01 mol) of <strong>[4170-90-5]2,4,6-trimethylbenzyl alcohol</strong>, 1.00 g (0.01 mol) of succinic acid anhydride, 3.25 g (0.01 mol) of cesium carbonate, and 100 ml of dioxane was stirred at reflux temperature for 4 hours. The reaction mixture was cooled to room temperature and then filtered to remove the solid cesium carbonate. The solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (acetone-hexane) to provide 1.167 g of succinic acid mono-(2,4,6-trimethylbenzyl) ester (46.62%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | NaClO2 (498 mg, 5.507 mmol) was added to a mixed solution containing 150 mg (1.101 mmol) of 3-phenylpropanol in a CH2Cl2 (3.7 mL)-NaH2PO4 aqueous solution (2.1 mL, 0.52 M solution being 1.0 equivalent), followed by stirring. Then, Me-AZADO+Cl- (11.1 mg, 0.05507 mmol) was immediately added, followed by vigorous stirring at room temperature until disappearance of the starting material 3-phenylpropanol and its aldehyde product 3-phenylpropanal was confirmed. After completion of the reaction, 2-methyl-2-butene (1.17 mL, 11.01 mmol) was added under cooling with ice, and an aqueous layer and an organic layer were separated under a weakly acidic condition. To the organic layer, a 10% sodium hydroxide aqueous solution was added to obtain a solution having a pH 11, from which organic substances other than the ionic carboxylic acid were extracted with diethyl ether. The remained aqueous layer was adjusted to pH 3 with 10% hydrochloric acid, and from the aqueous layer, a molecular type carboxylic acid was extracted with diethyl ether. The organic layer was washed with an aqueous sodium chloride solution and then dried over magnesium sulfate, and the solvent was distilled off under reduced pressure.The residue was dissolved in methylene chloride, and diazomethane was added under cooling with ice, and after confirming the completion of a methyl esterification reaction, stirring was continued at room temperature for a while. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 176 mg (yield: 97%) of a methyl ester.Cases wherein the reaction was carried out in the same manner, are shown with respect to the case where Me-AZADO+Cl- was employed and the case where TEMPO+CL- was employed. Here, in the Table, ?alcohol? represents the alcohol, ?time (hr)? represents the reaction time (unit: hr), ?yield (%)? represents the yield (%) which was calculated by the isolated yield of the methyl ester by the diazomethane. ?note? represents a note, ?trace? represents a trace amount, ?Additive? represents an additive, ?SASS? represents sodium stearate, and ?slight chlorination? means that slight chlorination was observed. ?Cat.? represents the catalyst. TABLE 1 yield % No. alcohol time [hr] note 1 1.5 77 97 2 1.5 63 93 3 10 trace 84 4 32 trace 86 5 5.5/6.5 trace 99/96Additive (5 mol %) PhCO2II/ SASS* 6 4.5 20 91 7 10 25 90 8 24 <16 <84 slight chlorination 9 3 <13 <92 slight chlorination cat. 20 mol % 10 5 - 92 11 1 - 88 12 15 trace 94 SASS*: Stearic Acid Sodium Salt | |
20% | NaClO2 (498 mg, 5.507 mmol) was added to a mixed solution containing 150 mg (1.101 mmol) of 3-phenylpropanol in a CH2Cl2 (3.7 mL)-NaH2PO4 aqueous solution (2.1 mL, 0.52 M solution being 1.0 equivalent), followed by stirring. Then, Me-AZADO+Cl- (11.1 mg, 0.05507 mmol) was immediately added, followed by vigorous stirring at room temperature until disappearance of the starting material 3-phenylpropanol and its aldehyde product 3-phenylpropanal was confirmed. After completion of the reaction, 2-methyl-2-butene (1.17 mL, 11.01 mmol) was added under cooling with ice, and an aqueous layer and an organic layer were separated under a weakly acidic condition. To the organic layer, a 10% sodium hydroxide aqueous solution was added to obtain a solution having a pH 11, from which organic substances other than the ionic carboxylic acid were extracted with diethyl ether. The remained aqueous layer was adjusted to pH 3 with 10% hydrochloric acid, and from the aqueous layer, a molecular type carboxylic acid was extracted with diethyl ether. The organic layer was washed with an aqueous sodium chloride solution and then dried over magnesium sulfate, and the solvent was distilled off under reduced pressure.The residue was dissolved in methylene chloride, and diazomethane was added under cooling with ice, and after confirming the completion of a methyl esterification reaction, stirring was continued at room temperature for a while. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 176 mg (yield: 97%) of a methyl ester.Cases wherein the reaction was carried out in the same manner, are shown with respect to the case where Me-AZADO+Cl- was employed and the case where TEMPO+CL- was employed. Here, in the Table, ?alcohol? represents the alcohol, ?time (hr)? represents the reaction time (unit: hr), ?yield (%)? represents the yield (%) which was calculated by the isolated yield of the methyl ester by the diazomethane. ?note? represents a note, ?trace? represents a trace amount, ?Additive? represents an additive, ?SASS? represents sodium stearate, and ?slight chlorination? means that slight chlorination was observed. ?Cat.? represents the catalyst. TABLE 1 yield % No. alcohol time [hr] note 1 1.5 77 97 2 1.5 63 93 3 10 trace 84 4 32 trace 86 5 5.5/6.5 trace 99/96Additive (5 mol %) PhCO2II/ SASS* 6 4.5 20 91 7 10 25 90 8 24 <16 <84 slight chlorination 9 3 <13 <92 slight chlorination cat. 20 mol % 10 5 - 92 11 1 - 88 12 15 trace 94 SASS*: Stearic Acid Sodium Salt |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h;Inert atmosphere; | General procedure: Benzyl alcohol (1.00 mmol), N,N-dimethylamino acid (1.20 mmol), 1,3-dicyclohexylocarbodiimide (1.20) mmol and DMAP (0.10 mmol) were stirred in dry DCM (5 mL) under an argon atmosphere for 24 h. The precipitate was removed by filtration, and the residue was washed with DCM (5 mL). The solvent was evaporated, and the residue was purified by flash column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With zinc(II) iodide; In dichloromethane; for 17h;Reflux; Inert atmosphere; | To a 2-necked 500mL flask under nitrogen was added mesitylmethanol 1 (5g, 33.3mmol) to dichloromethane (133 mL, 0.25M) and all of the solid dissolved in the solvent. Zinc Iodide (5.3 lg, 16.64mmol) was added to the solution in one portion. The zinc iodide was not soluble in the solution, and white solid crashed out of the solution. Thioacetic acid (7.17mL, 100 mmol) was added to the solution in one portion causing the solution to turn pale yellow. The flask was affixed with a water condenser and was covered in aluminum foil. The solution was heated to reflux for 17 hours and was allowed to cool to room temperature. Once cool, the solution was then quenched with water (40mL) and this solution was transferred to a separatory funnel. The organic layer was collected and the aqueous layer was extracted with dichloromethane (4 x 7mL).The combined organic fractions were washed with brine (1 x lOOmL), dried over sodium sulfate, filtered, and concentrated on the high vacuum to give the title compound 2 as a brown oil, 7.7g, 111%. [00102] ¾ NMR (400MHz, CDC13) delta 6.84 (s, 2H), 4.18 (s, 2H), 2.35 (s, 3H), 2.30 (s, 6H), 2.25 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | General procedure: To a stirred mixture of Ph2PCl (6.0 mmol), NaI (6.0 mmol) and anhydrous CH3CN (5.0 mL) was added alcohol 2(1.0 mmol) at room temperature under argon atmosphere. The reaction mixture was stirred at 80 C in oil bath for 12 h. When the reaction temperature was cooled to room temperature, 30 % H2O2 aqueous (0.5 mL) was slowly added, and stirred for another 10 minutes. The organic layer was extracted with dichloromethane, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to obtain the corresponding phosphine oxide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | General procedure: To a stirred mixture of Ph2PCl (6.0mmol), NaI (6.0 mmol) and anhydrous CH3CN (5 mL) was added alcohol 2 (1.0 mmol) at room temperature under argon atmosphere. The reaction mixture was stirred at 80 C in oil bath for 12 h. When the reaction temperature was cooled to room temperature, aqueous Na2S2O3 (2.0 mL) was added to the reaction mixture, and stirred for another 10 minutes. The organic layer was extracted with dichloromethane, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to obtain the corresponding phosphine sulfoxide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (R)-3,3?-bis(2,4,6-triisopropylphenyl)-6,6?-dinitro-1,1?-binaphthylphosphate; In chloroform; at 20℃; for 5h; | General procedure: To a mixture of 2 (0.10 mmol), catalyst 1 (5mol%), and alcohol 3 (0.11 mmol), was added CHCl3 (0.25 mL) at rt. The mixture was stirred at rt for indicated time in the tables and diluted with Et2O (5 mL). The organic layer was extracted with saturated aq. Na2CO3 (3 mL),and the aqueous layer was acidified with 6 N HCl. The aqueous layer was extracted with Et2O (5 mL), and the organic layer was dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography to afford the desired product 4. |
Tags: 4170-90-5 synthesis path| 4170-90-5 SDS| 4170-90-5 COA| 4170-90-5 purity| 4170-90-5 application| 4170-90-5 NMR| 4170-90-5 COA| 4170-90-5 structure
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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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