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CAS No. : | 612-16-8 | MDL No. : | MFCD00004611 |
Formula : | C8H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WYLYBQSHRJMURN-UHFFFAOYSA-N |
M.W : | 138.16 | Pubchem ID : | 69154 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 39.06 |
TPSA : | 29.46 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) : | -6.34 cm/s |
Log Po/w (iLOGP) : | 1.92 |
Log Po/w (XLOGP3) : | 1.13 |
Log Po/w (WLOGP) : | 1.04 |
Log Po/w (MLOGP) : | 1.21 |
Log Po/w (SILICOS-IT) : | 1.67 |
Consensus Log Po/w : | 1.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.72 |
Solubility : | 2.63 mg/ml ; 0.019 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.34 |
Solubility : | 6.28 mg/ml ; 0.0455 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.33 |
Solubility : | 0.654 mg/ml ; 0.00473 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: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
98% | With lithium bromide monohydrate; [bis(acetoxy)iodo]benzene In 2,2,2-trifluoroethanol at 20℃; for 0.166667 h; | General procedure: To a solution of alkoxybenzylalcohol 1 (0.2 mmol) in CF3CH2OH (1 mL) were added LiBr·H2O (0.2 mmol) and PhI(OAc)2 (0.2 mmol) atroom temperature. After completion of the reaction as indicated by TLC monitoring, saturated aq. Na2SO3 wasadded and the mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, driedover anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford pure monobrominated compounds 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With phosphorus tribromide; In benzene; at 20℃; | General procedure: benzyl alcohols (1 mmol) in dry benzene (15 mL) and phosphorus tribromides (0.5 mL) and stirred at room temperature to get respective benzyl bromides in quantitative yields, usual work-up. |
With hexabromoacetone; triphenylphosphine; In acetonitrile; at 40℃; for 2.75h;Inert atmosphere; | A mixture of alcohol (1.2 mmol) and triphenylphosphine (1.8 mmol) was stirred in dry acetonitrile (6 mL) for 15 min. Hexabromoacetone (0.6 mmol) was added and the stirring continued at 40 under a nitrogen atmosphere. Conversion of the alcohol into the bromide was followed by 1H NMR analysis on a sample previously quenched with cold water. | |
With phosphorus tribromide; In dichloromethane; for 1h;Cooling with ice; | 1.02 g (7.38 mmol, 1.0 eq) compound 13c was dissolved in 40 ml CH2Cl2, then 0.84 ml (8.90 mmol, 1.2 eq) PBr3 was added under the condition of ice water bath. After reacting for an hour, a little saturated sodium bicarbonate solution was added to wash the organic phase followed by twice wash with saturated sodium chloride solution, then dried over anhydrous sodium sulfate and desolventizing to gain 1.15 g reddish colored oily material (Compound 8-2c), yield 77.5%. The crude product was used without purification in the next step directly. Compound 8-2a, 8-2b, and 8-2d can be obtained in the same way from compound 13a, 13b, and 13d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With thionyl chloride; triethylamine; In dichloromethane; at 20℃; for 1h; | 2-methoxybenzyl alcohol (268 mu Iota_, 2.0 mmol) and triethylamine (335 mu Iota_, 2.4 mmol) were dissolved in anh. DCM (7 ml_). Thionyl chloride (218 muIota_, 3.0 mmol) was added slowly. The reaction mixture was stirred at RT for 1 h. The reaction mixture was washed with an aqueous solution of HCI 1 N. The organic phase was dried over MgS04. The solvent was removed under reduced pressure to give the desired 2-methoxybenzyl chloride (300 mg, 96 %) as a yellowish oil . 4-(4-chlorophenyl)-1 -(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylic acid (example 74, 85 mg, 0.26 mmol) was dissolved in anhydrous DM F (1 m L) then cesium carbonate (169 mg, 0.52 mmol) and 2-methoxybenzyl chloride (81 mg, 0.52 mmol) were added. The reaction mixture was stirred at RT for 18 h. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over MgS04. The solvent was removed under reduced pressure. Purification of the crude by flash chromatography using a mixture of Cyclohexane/EtOAc (8/2) as eluent gave the desired (2- meth oxyphenyl )methyl 4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4- dihydropyridine-5-carboxylate as a yellowish oil (36 mg, 31 %). 1H NMR (300 MHz, CDCI3) delta 2.60 (s, 3H), 2.71 (dd, J = 15.9, 2.4 Hz, 1 H), 2.91 (dd, J = 15.9, 7.6 Hz, 1 H), 3.31 (s, 3H), 3.36 (ddd, J = 9.8, 8.3, 3.7 Hz, 1H), 3.46 (dt, J = 9.8, 4.2 Hz, 1H), 3.74 (s, 3H), 3.69-3.78 (m, 1H), 4.13-4.21 (m, 2H), 5.10 (d, J = 12.9 Hz, 1H), 5.19 (d, J= 12.9 Hz, 1H), 6.80-6.85 (m, 2H), 6.98 (dd, J = 7.8, 1.6 Hz, 1H), 7.09 (d, J = 8.4 Hz, 2H), 7.19 (d, J = 8.4 Hz, 2H), 7.26 (t, J = 7.8 Hz,1H). 13C NMR (75 MHz, CDCI3) delta 17.0, 36.8, 38.6, 41.8, 55.1, 58.8, 61.8, 71.0, 110.1, 110.3, 120.2, 124.2, 128.4, 128.6, 129.1, 129.2, 132.4, 139.8, 150.6, 157.2, 167.1, 169.0. MS [M+H]+ 444. HRMS : calcd for C24H27N05CI, [M+H]+ 444.1578, found 444.1585. |
94% | With oxalyl dichloride; 1-methyl-3-(2-(3-methyl-2-oxoimidazolidin-1-yl)ethyl)-1H-imidazol-3-ium hexafluorophosphate; at 20 - 60℃; | General procedure: The solution of ionic-liquid-supported DMI 7 (2.2 mmol) in[bmim]PF6 (2 mL) was added to oxalyl chloride (2.0 mmol), andthe mixture was stirred at 60 C for 2 h. The mixture was then added to the appropriate alcohol (1.5 mmol), and the resultingmixture was stirred at r.t. overnight. Finally, the mixture wasextracted with hexane 10 mL x 3, and the organic layer wasconcentrated. |
88% | With 1-methyl-pyrrolidin-2-one; benzenesulfonyl chloride; In 1,2-dichloro-ethane; at 80℃; for 1.5h; | General procedure: In a round-bottom flask, benzylic alcohol 1a (10 mmol, 2.0 equiv.), benzenesulfonyl chloride 2a (13 mmol, 1.3 equiv.) and NMP (2.5 equiv.). Then, DCE (3 mL) were added. The mixture was stirred at 80 C for 1.5 h. After completion of the reaction (monitoredby TLC), water (10 mL) was added and the mixture was extracted with ethyl acetate (3*10 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel to give the desired alkyl chlorides 3. |
With thionyl chloride; In dichloromethane; | i 2-Methoxybenzyl chloride In a nitrogen atmosphere, 2.00 g (14.5 mmol.) of 2-methoxybenzyl alcohol was dissolved in 10 ml of dichloromethane. The obtained solution was placed in an ice-bath, and to this was dropwise added a solution of 1.06 ml (14.6 mmol.) of thionyl chloride in 2 ml of dichloromethane. The mixture was then stirred at room temperature for 1.5 hours. The mixture was placed under reduced pressure at room temperature to distill off the solvent to give 2.32 g of the desired compound as a yellow oil. 1 H-NMR (CDCl3) delta:3.87 (s, 3H), 4.64 (s, 2H), 6.7-7.4 (m, 4H). | |
With chloro-trimethyl-silane; triethylamine; In dichloromethane; at 0 - 20℃; for 18h; | Step 2: Preparation of 1-(chloromethyl)-2-methoxybenzene To a solution of <strong>[612-16-8](2-methoxyphenyl)methanol</strong> (1.15 g, 8.32 mmol) and triethylamine (1.24 g, 12.3 mmol, 1.7 mL) in methylene chloride (16 mL) at 0 C. was added dropwise chlorotrimethylsilane (0.939 g, 8.65 mmol). The reaction mixture was stirred in the cooling bath for an additional 30 min after which the cooling bath was removed and stirred at room temperature for 18 h. The reaction mixture was washed with water (10 mL*2), dried over sodium sulfate, filtered and concentrated to give crude 1-(chloromethyl)-2-methoxybenzene (1.36 g, crude) as an orange oil. The material was used directly in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With C15H29MnNO3P2(1+)*Br(1-); potassium <i>tert</i>-butylate; hydrogen In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; Autoclave; | |
82% | With ethanol; potassium <i>tert</i>-butylate; C39H41FeMnN2O5P(1+)*Br(1-); 1-Methylnaphthalene In <i>tert</i>-butyl alcohol at 100℃; for 22h; Inert atmosphere; Schlenk technique; enantioselective reaction; | |
81% | Stage #1: 2-methoxybenzoic acid methyl ester With phenylsilane; fac-[Mn-(xantphos)(CO)3Br] at 100℃; for 6h; Inert atmosphere; Stage #2: With water; sodium hydroxide In methanol at 20℃; Inert atmosphere; |
60% | With sodium tetrahydroborate In 1,4-dioxane; water for 24h; Ambient temperature; | |
39% | With sodium tetrahydroborate; sodium methylate In methanol at 25℃; for 3h; Inert atmosphere; | |
4% | With C24H30Cl2NPRuS2; potassium <i>tert</i>-butylate; hydrogen In dichloromethane; toluene at 80℃; for 5h; Autoclave; | |
With methanol; copper oxide-chromium oxide; barium(II) oxide at 160 - 162℃; Hydrogenolyse; | ||
With α-picoline; N-phenyl benzoyl amide; sodium tetrahydroborate | ||
100 % Chromat. | With sodium tetrahydroborate In methanol; 1,2-dimethoxyethane for 1h; Heating; | |
With diisobutylaluminium hydride In diethyl ether; toluene at -70 - 20℃; | ||
65 %Chromat. | With dichlorido-bis[(2-diphenylphosphino)ethyl]amine-cobalt(II); hydrogen; sodium methylate In 1,4-dioxane at 120℃; for 24h; Autoclave; | |
With C43H42NOP3Ru; hydrogen In 1,4-dioxane; methanol at 130℃; for 17h; Glovebox; Autoclave; | ||
With C22H14MnN2O4(1+)*BF4(1-); potassium hydride In tetrahydrofuran at 50℃; Inert atmosphere; Glovebox; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With ethanol; potassium <i>tert</i>-butylate; C39H41FeMnN2O5P(1+)*Br(1-); 1-Methylnaphthalene In <i>tert</i>-butyl alcohol at 100℃; for 22h; Inert atmosphere; Schlenk technique; enantioselective reaction; | |
With lithium aluminium tetrahydride; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In the inert gas N2 atmosphere, after dehydration and deoxidation treatment to the reaction bottle after adding 2 - methoxybenzoic acid (76.2 mg, 0.5 mmol), for adding liquid-[...] borane (290 mul, 2 mmol), reacting at room temperature 12 hours, the reaction out of the glove box, in order to have three methoxybenzene (84.23 mg, 0.5 mmol) as the internal standard, CDCl3 for dissolving, stirring 10 minutes, sampling, with nuclear magnetic resonance. Calculated 1 H and the yield is 99%. The product of nuclear magnetic data: The residue is added to the sample in 1 g silica gel, in order to 3 ml methanol as a solvent, 50 C lower reaction 3 h, the borate further hydrolysis alcohol, after the reaction, extracted with ethyl acetate three times, the combined organic layer, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, through the silica gel (100 - 200 mesh) column chromatography purification, ethyl acetate/hexane (1:5) mixture as the eluent, to obtain the pure primary alcohol, separation and the yield is 90%. | |
90% | In the inert gas N2 atmosphere, after dehydration and deoxidation treatment to the reaction bottle after adding 1 - naphthoic acid (85.4 mg, 0.5 mmol, gun for adding [...] borane (289 mul, 2 mmol), reacting at room temperature 12 hours, the reaction out of the glove box, in order to have three methoxybenzene (83.42 mg, 0.5 mmol) as the internal standard, CDCl3 for dissolving, stirring 10 minutes, sampling, with nuclear magnetic resonance. Calculated 1 H and the yield is 91%. The product of nuclear magnetic data: The residue is added to the sample in 1 g silica gel, in order to 3 ml methanol as a solvent, 50 C lower reaction 3 h, the borate further hydrolysis alcohol, after the reaction, extracted with ethyl acetate three times, the combined organic layer, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, through the silica gel (100 - 200 mesh) column chromatography purification, ethyl acetate/hexane (1:5) mixture as the eluent, to obtain the pure primary alcohol, separation and the yield is 91%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With lithium bromide monohydrate; [bis(acetoxy)iodo]benzene; In 2,2,2-trifluoroethanol; at 20℃; for 0.166667h; | General procedure: To a solution of alkoxybenzylalcohol 1 (0.2 mmol) in CF3CH2OH (1 mL) were added LiBr·H2O (0.2 mmol) and PhI(OAc)2 (0.2 mmol) atroom temperature. After completion of the reaction as indicated by TLC monitoring, saturated aq. Na2SO3 wasadded and the mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, driedover anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford pure monobrominated compounds 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With Cu(2+)*Zr(4+)*2PO4(3-) = CuZr(PO4)2; at 60℃; for 0.5h; | General procedure: ZPCu (2 mol%) was added to a mixture of phenol (1 mmol)and AA (2 mmol), and the resulting mixture was stirred at 60 C for the specified time (Scheme 2). Upon completion of the reaction(as determined by GC), the catalyst was separated from the reaction mixture by centrifuge, then the supernatant was collected and diluted with 10% NaHCO3 solution (10 ml) before being extracted with Et2O (2 . 10 ml). The combined organic extracts were washed and then dried over anhydrous CaCl2 before being evaporated to dryness under vacuum to give the desired product. In some cases, it was necessary for the product to be purified by column chromatography over silica gel eluting with a mixture of cyclohexane and ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With bismuth(III) chloride; palladium diacetate; potassium carbonate at 20℃; for 2h; chemoselective reaction; | |
85% | With sodium methylate; potassium iodide at 15℃; Electrochemical reaction; | |
53% | With oxygen; potassium carbonate at 70℃; for 48h; |
53% | With oxygen; potassium carbonate at 30℃; for 24h; Irradiation; | |
40 %Chromat. | With oxygen at 55℃; for 24h; Irradiation; Sealed tube; Green chemistry; | |
With oxygen at 60℃; for 48h; | ||
With oxygen at 60℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With palladium dichloride In methanol at 40℃; for 18h; Inert atmosphere; Green chemistry; chemoselective reaction; | |
50% | With chlorocarbonylbis(triphenylphosphine)iridium(I); hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Sealed tube; | |
50% | With chlorocarbonylbis(triphenylphosphine)iridium(I); hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Sealed tube; |
Multi-step reaction with 3 steps 1: 77 percent / sodium iodide; sodium hydride / tetrahydrofuran / 0 - 20 °C 2: sulfuryl chloride / CH2Cl2 / -78 °C 3: lithium; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 1 h / 0 °C | ||
Multi-step reaction with 2 steps 1: benzene; hydrogen bromide 2: Behandeln des Reaktionsgemisches mit Wasser | ||
98 %Chromat. | With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.166667h; Inert atmosphere; | |
98 %Chromat. | With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.166667h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 80 percent / PBr3 / toluene / 0.17 h / 100 °C 2: 1.) NaOEt / 1.) EtOH, 2.) EtOH, 3 h 3: 94 percent / aq. NaOH / 6 h / Heating 4: 63 percent / Aspergillus acylase I, aq. KOH / 72 h / 40 °C 5: 77 percent / Et3N / H2O; dioxane / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: 86 percent / thionyl chloride, pyridine / toluene / Ambient temperature 2: 1.) Na, 3.) 2N NaOH 3: 88 percent / acetic anhydride / 2 h / Heating 4: 54 percent / AlCl3 / nitrobenzene / 0.08 h 5: 96 percent / H2 / 10percent Pd/C / acetic acid / 70 - 80 °C / 760 Torr 6: 75 percent / diphenylphosphoryl azide, Et3N / 18 h / Heating 7: 74 percent / 4N HCl / ethyl acetate / 3 h 8: 66 percent / K2CO3 / acetonitrile / 96 h / Ambient temperature 9: 84 percent / 48percent HBr / 2 h / 120 - 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 86 percent / thionyl chloride, pyridine / toluene / Ambient temperature 2: 1.) Na, 3.) 2N NaOH 3: 88 percent / acetic anhydride / 2 h / Heating 4: 54 percent / AlCl3 / nitrobenzene / 0.08 h 5: 96 percent / H2 / 10percent Pd/C / acetic acid / 70 - 80 °C / 760 Torr 6: 75 percent / diphenylphosphoryl azide, Et3N / 18 h / Heating 7: 74 percent / 4N HCl / ethyl acetate / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 40 percent / dichlorobenzene / 40 h / Heating 2: 100 percent / 10percent aq. NaOH / methanol / 18 h / Heating | ||
Multi-step reaction with 2 steps 1: toluene / 14 h / 170 °C / Microwave irradiation; Inert atmosphere 2: sodium hydroxide / water; ethanol / 48 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 99% | With potassium tert-butylate; copper diacetate; In 1,4-dioxane; at 130℃; for 48h;Inert atmosphere; | General procedure: To a solution of Cu(OAc)2 (0.025 mmol, 0.0046 g) and potassium tert-butoxide (0.175 g, 2.5 mmol) in anhydrous dioxane (3 mL), the corresponding amine 1 (2.5 mmol) or the triphenylphosphoranylidenaniline 18 (2.5 mmol) and the correspondent alcohol 2 or 4 (3.75 mmol) were added successively under inert argon atmosphere. After 2 or 5 days of reaction at 130 C (see Table 2 and Scheme 2), the resulting mixture was hydrolyzed with a saturated solution of ammonium chloride (10 mL). The mixture was extracted with AcOEt (3×10 mL) and washed with brine (10 mL), after drying with anhydrous MgSO4, was filtered on Celite and the solvents were removed under low pressure(15-18 Torr). The resulting mixture was purified by column chromatography (if needed). |
84% | With sodium hydroxide; at 150℃; for 24h;Schlenk technique; | General procedure: The mixture of benzyl alcohol (1a, 0.3244 g, 3.0 mmol,1.5 equiv.), 2-aminopyridine (6a, 0.1882 g, 2.0 mmol), and NaOH (0.0400 g, 1.0 mmol, 50 mol%)was sealed under air in a 20 mL Schlenk tube and then stirred at 150 oC for 24 h. After completion,the reaction was monitored by TLC and/or GC-MS (>99% GC conversion) and the crude productwas purified by column chromatography using ethyl acetate and petroleum ether as eluent. Thetarget product 7a was obtained in 89% isolated yield. White solid. 1H NMR (500 MHz, CDCl3): delta 8.10 (dd,J = 5.0 Hz, J = 1.0 Hz, 1H), 7. 39-7.36 (m, 1H), 7.31 (d, J = 7.5 Hz, 1H), 7.26-7.23 (m, 1H),6.92-6.87 (m, 2H), 6.56-6.54 (m, 1H), 6.39 (d, J = 7.5 Hz, 1H), 5.01 (b, 1H), 4.48 (d, J = 6.0 Hz,2H), 3.85 (s, 3H). 13C NMR (125.4 MHz, CDCl3): delta 158.9, 157.4, 148.2, 137.3, 128.8, 128.3, 127.1,120.5, 112.8, 110.2, 106.7, 55.3, 41.7. MS (EI): m/z (%) 214 (60), 183 (92), 136 (45), 121 (35), 105(31), 91 (100), 78 (48), 65 (25), 51 (14). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium hydroxide; copper(l) chloride; at 120℃; for 24h; | The reactants used were o-methoxybenzyl alcohol (i.e., R1 in the formula (I) was ortho OCH3) 1.0 mmol(138.2 mg), experimental procedure and procedure with Example 1, aqueous ammonia (1.7 mol / L) 5.0 mL,The amount of catalyst used in cuprous chloride was 8 mol% (7.9 mg)TEMPO is used in an amount of 8 mol% (12.5 mg)The reaction temperature was 120 and the reaction time was 24h. The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 10: 1) to give the target product as 123.9 mgYield 93%. |
90% | With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-Phenylalanin; sodium hydroxide; In methanol; at 60℃; for 24h;Cooling with ice; | General procedure: Reactants used were p-methylbenzyl alcohol (122.03g, 1000mmol, i.e., of formula (I) wherein R is methyl, n = 1, m = 0 , X = C),cuprous iodide (9.50 g of , 50mmol), N- phenylglycine (7.51g, 50mmol), TEMPO ( 7.80g, 50mmol),sodium hydroxide (4.00g, 100mmol), aqueous ammonia (300mL, 25 ~ 28%) ,ethanol, 800mL, in an ice bath under the condition, with oxygen round bottom flask is evacuated of air ventilation 3 times, and then the system was stirred at 25 , 24h, after completion of the reaction, the reaction solution was cooled to room temperature, rotary evaporated to remove the solvent, the residue was washed with water filtered and dried The product was 107.64g, yield 92%. he reaction was used for the o-methoxybenzyl alcohol (138.02g, 1000mmol, i.e., of formula (I) wherein R is 2-methoxy n = 1, m = 0 , X = C),the same experimental methods and procedures Example 2, except that: copper iodide (9.50g, 50mmol), N- phenylalanine (8.26g, 50mmol), TEMPO ( 7.80g, 50mmol),sodium hydroxide (4.00g, 100mmol ), ammonia (300mL, 25 ~ 28%) ,methanol 800mL, stirred at 60 for 24h, to give the final product 119.71g, yield 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; nickel diacetate In 1,4-dioxane; toluene at 80℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; | |
89% | With potassium <i>tert</i>-butylate In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; | |
84% | With Ru(η(2)-2-(2'-pyridyl)phenyl)Cl(CO)(PPh3)2; potassium <i>tert</i>-butylate In toluene at 80℃; for 6h; Inert atmosphere; Schlenk technique; Green chemistry; |
78% | With C23H21MnN2O3P(1+)*Br(1-); potassium <i>tert</i>-butylate In 1,4-dioxane at 130℃; for 15h; Schlenk technique; Inert atmosphere; Green chemistry; | |
73% | With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); 2-(3,5-dimethylpyrazol-1-yl)-6-(pyrazol-3-yl)-pyridine; potassium <i>tert</i>-butylate at 140℃; for 18h; | |
72% | With potassium <i>tert</i>-butylate In 1,3,5-trimethyl-benzene at 164℃; for 6h; | |
70% | With C29H55IrN3P2(1+)*Cl(1-); potassium <i>tert</i>-butylate In toluene at 120℃; for 15h; Schlenk technique; Inert atmosphere; Glovebox; | |
60% | With C20H37ClN2OPRu; potassium <i>tert</i>-butylate In neat liquid at 140℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane 2: sodium hydride / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With caesium carbonate In dimethyl sulfoxide at 60℃; for 18h; Schlenk technique; Inert atmosphere; | 4.1 General procedure for the synthesis of the products (4-phenylphenol with pentafluorobenzene as the example) General procedure: 4-Phenylphenol 2 (34.0mg, 0.2mmol) and cesium carbonate (97.7mg, 0.3mmol) were weighed to a sealed Schlenk (25mL) under Ar atmosphere. Pentafluorobenzene 1a (50.4mg, 0.3mmol) and DMSO (2.0mL) were added to the sealed Schlenk via syringe at room temperature respectively. The mixture was stirred at room temperature until the completion of the reaction (by TLC). Water (5mL) was added and the mixture was extracted with ethyl acetate (3×10mL). The organic extracts were combined, dried with anhydrous magnesium sulfate and then concentrated in vacuo. The residue was purified on silica gel to afford the product 3o (54.1mg, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 21% 2: 75% | With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h; Schlenk technique; | General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 °C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57%) as a pale yellow solid. Yields of 57% of 2a and 38% of benzaldehyde (3a)15 were observed by NMR analysisof the crude product using CH2Br2 as an internal standard and by comparison with spectra reported in the literature. |
With 2,2-diphenyl-1-picrylhydrazyl; tungusten oxide/alumina; oxygen In acetone at 80℃; for 3h; | 2.3. Procedure for the catalytic oxidation of benzyl alcohol in acetone General procedure: A 50 mL three-necked glass flask was charged with a mixture ofDPPH (98.6 mmg, 0.25 mmol),WO3/Al2O3 (0.844 g,W: 3 mmol), alcohol(50 mmol), and 30 mL acetone. One neck was connected with awater condenser to reflux. Besides, there must be a deflated balloonon the top of the condenser to collect the evaporated acetone. And anotherneck was connected with a dropping funnel to add acetone.Then an oxygen steel cylinder was used to slowly provide the oxygenfor the reaction through the third neck with an air duct. The ventilationspeed must be adjusted according to the size of the balloon. Moreover,to maintain the airtightness of the whole reaction, the liquid level inthe dropping funnel should be kept in a certain height. Then themixturewas stirred at 80 °C for 4 h. The reaction mixture was subjected to GCanalysis to supervise the reaction process till the oxidation ended. | |
With Ti0.85V0.15O2; dihydrogen peroxide In methanol at 20℃; for 2h; |
In N,N-dimethyl-formamide at 120℃; for 4h; Inert atmosphere; | ||
With hydrogenchloride; dichloro(4,11-dimethyl-1,4,8,11-tetraazabicyclo[6.6.2]hexadecane)manganese(II); dihydrogen peroxide In water; acetonitrile at 29.84℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73%Chromat. | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; at 25℃; for 12h; | General procedure: DBDMH (20 mmol) was added in portion wise to a mixture of 1b (5 mmol) andmethanol (30 ml). The reaction was kept at room temperature. After the mixture wasstirred for 12h, the methanol was vacuum evaporated. The residue was dissolved byMTBE (30 ml), washed with water (330 ml).The organic extracts was dried byanhydrous MgSO4, filtered, and concentrated under reduce pressure. The residue waspurified by column chromatography (silica gel: petroleum ether/ethyl acetate, 30:1) toafford the product as light yellow solid ( 92% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In toluene at 110℃; for 96h; Inert atmosphere; | General Procedure for the Preparation of 3 General procedure: To a solution of [Cp*IrCl2]2 (0.0025 mmol), amino acid 2(0.65 mmol), and NaHCO3 (0.05 mmol) in toluene (3 mL) under an atmosphere of argon was added alcohol 1 (0.5mmol). The resulting mixture was stirred at 110 °C for a certain period of time. The reaction mixture was cooled tor.t., and H2O (5 mL) was then added. The resulting solution was extracted with EtOAc. Purification on silicon gel afforded the desired products 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium carbonate; In neat (no solvent); at 120℃;Green chemistry; | General procedure: Typically, o-phenylenediamine (1.3 mmol) or 2-aminothiophenol (1 mmol), benzyl alcohols (1 mmol), Na2CO3 (20 mol%), and Pd-NPs/Cu2(BDC)2(DABCO) (20 mg, 0.01 mol%) were added to a round-bottom flask. The reaction mixture was heated to 120 Cand stirred at for the appropriate time in air (TLC monitoring). Ethyl acetate was added to the reaction mixture and catalyst was filtered. For the purification of impure products, chromatography on silica gel was performed (EtOAc:Hep. (1:6)). The entire products characterized by melting point, CHN, 1H-NMR and13C-NMR spectroscopy. |
74% | In neat (no solvent); at 135℃; for 24h;Green chemistry; | General procedure: Reactions were performed in a magnetically stirred round bottomed flask fitted with acondenser and placed in a temperature controlled oil bath. 1,2-Diamine (2 mmol)was added to alcohol (3 mmol) and the reaction mixture was allowed to stir at 135C in an open (air) atmosphere. After disappearance of the diamine (reaction was monitored by TLC)or after the appropriate time, the reaction mixture was cooled to roomtemperature. The crude residue was further purified by column chromatography using silica gel (100-200 mesh) to afford pure products. All the products wereidentified on the basis of NMR and mass spectral data |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.05 g | Reference Production Example 1 In a nitrogen atmosphere, a tetrahydrofuran solution (10 ml) of 829 mg (6 mmol) of 2-methoxybenzyl alcohol was added dropwise to a tetrahydrofuran suspension (20 ml) of 280 mg (7 mmol) of 60% sodium hydride at 0 C., and the mixture was stirred at room temperature for 30 minutes. A tetrahydrofuran solution (10 ml) of 1.21 g (5 mmol) of <strong>[4175-78-4]2,5-dibromothiazole</strong> was added to the reaction mixture at room temperature, and the resulting product was stirred for 4 hours. The reaction mixture was cooled to 0 C., then, water was added thereto, and the resulting product was extracted three times with ethyl acetate. After the organic layers were combined and concentrated, the residue was purified by silica gel column chromatography, whereby 1.05 g of 5-bromo-2-(2-methoxybenzyloxy)thiazole (compound (4-1)) was obtained. 1H-NMR (CDCl3) delta: 3.86 (3H, s), 5.49 (2H, s), 6.90 (1H, d, J=8.3 Hz), 6.93 (1H, dt, J=1.5, 7.5 Hz), 7.07 (1H, s), 7.33 (1H, dt, J=1.5, 7.5 Hz), 7.43 (1H, dd, J=1.5, 7.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium hydroxide; In benzene; at 100℃; for 18h;Inert atmosphere; | A 50 ml three-necked flask equipped with a stirring reflux device was charged with 1 mmol of 2-diethylphosphine aniline,1.3 mmol of o-methoxybenzyl alcohol, 1 mmol2-dicyclohexylphosphine oxide, 1 mmol RuCl2 (PPh3) 3, 1.1 mmol potassium hydroxide, 20 ml benzene and heating at a temperature of 100 C for 18 h under a nitrogen atmosphere,After cooling and filtering, the resulting solid was recrystallized from a mixed solvent of CH 2 Cl 2 and petroleum ether to give product 15 in a yield of 80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28 % de | With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydroxide; copper(ll) bromide In formamide; acetonitrile at 65℃; for 24h; Schlenk technique; Overall yield = 82 %; Overall yield = 169 mg; diastereoselective reaction; | α,β-Unsaturated Esters 3, α,β-Unsaturated Ketones 4, and α,β-Unsaturated Nitriles 5; General Procedure General procedure: Alcohol (1 mmol), phosphonium salt (1.1 mmol), NaOH (1.1 mmol),CuBr2 (5 mol%), 2,2′-bipy (5 mol%), and TEMPO (5 mol%) were mixed in MeCN and HCONH2 (1:1, 2 mL) in a 100-mL Schlenk tube with an air balloon, and the mixture was stirred at 65 °C for 24 h (monitoring by TLC and/or GC-MS). After completion, product was purified by column chromatography (EtOAc and petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86 % de | With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydroxide; copper(ll) bromide In formamide; acetonitrile at 65℃; for 24h; Schlenk technique; Overall yield = 93 %; Overall yield = 221 mg; diastereoselective reaction; | α,β-Unsaturated Esters 3, α,β-Unsaturated Ketones 4, and α,β-Unsaturated Nitriles 5; General Procedure General procedure: Alcohol (1 mmol), phosphonium salt (1.1 mmol), NaOH (1.1 mmol),CuBr2 (5 mol%), 2,2′-bipy (5 mol%), and TEMPO (5 mol%) were mixed in MeCN and HCONH2 (1:1, 2 mL) in a 100-mL Schlenk tube with an air balloon, and the mixture was stirred at 65 °C for 24 h (monitoring by TLC and/or GC-MS). After completion, product was purified by column chromatography (EtOAc and petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydroxide; copper(ll) bromide; In formamide; acetonitrile; at 65℃; for 24h;Schlenk technique; | General procedure: Alcohol (1 mmol), phosphonium salt (1.1 mmol), NaOH (1.1 mmol),CuBr2 (5 mol%), 2,2?-bipy (5 mol%), and TEMPO (5 mol%) were mixed in MeCN and HCONH2 (1:1, 2 mL) in a 100-mL Schlenk tube with an air balloon, and the mixture was stirred at 65 C for 24 h (monitoring by TLC and/or GC-MS). After completion, product was purified by column chromatography (EtOAc and petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With bromopentacarbonylmanganese(I); [(E)-2-(2-(1-(2-pyridyl)ethylidene)-indenyl)pyridine]; In toluene; at 135℃; for 48h; | In the glove box, Mn(CO)5Br (0.005mmol), [(E)-2-(2-(1-(2-pyridyl)ethylidene)-indenyl)pyridinium](0.006 mmol),Add 1.0 mL of toluene, stir for two hours, add 2-methylquinoline 4 (2 mmol),2i (1 mmol), after reacting at 135 C for 48 hours, the reaction was stopped, and the solvent was evaporated to dryness.Column chromatography ethyl acetate / petroleum ether (1:10),Trans-disubstituted olefin derivative 3ai. The product was a white solid with a yield of 93%. |
82% | With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; oxygen; In tetrahydrofuran; at 50℃; | Add 2-methylquinoline (1mmol), 2-methoxybenzyl alcohol (2.5mmol), TEMPO (0.1mmol), Fe (NO3) 3.9H2O (0.1mmol) andt-BuOK (2mmol) was sequentially added to a flask containing 2mL of THF,The air in the flask was replaced with oxygen, and the reaction was stirred at 50 C.The reaction process was monitored by thin layer chromatography. After the reaction was completed, it was quenched with water (10 mL).The reaction product was extracted with ethyl acetate (3 × 20 mL), washed with saturated brine (20 mL), dried over anhydrous Na2SO4, filtered, and the resulting filtrate was concentrated, and passed through silica gel column chromatography (200-300 mesh, the developing solvent was petroleum ether). (20: 1 mixed solution with ethyl acetate in volume ratio) yielded 215.0 mg of product with a yield of 82%. |
82% | With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; potassium tert-butylate; oxygen; In tetrahydrofuran; at 50℃; for 8h; | General procedure: The oxidative olefination reaction was carried out in a 10 mL long-necked, round-bottomed flask equipped with a magnetic stirrer with an oxygen balloon at 50 C. Typically, 2-methylquinoline (1 mmol, 143.2 mg), phenylmethanol (2.5 mmol, 270.4 mg), TEMPO (0.05 mmol, 7.8 mg), Fe(NO3)3·9H2O (0.05 mmol, 20.2 mg), tBuOK (2 mmol, 224.4 mg) and 18-crown-6 (1 mmol, 264.3 mg) were charged sequentially into the flask with 3 mL THF. The flask was then evacuated under reduced pressure, followed by the attachment of an oxygen balloon. The resulting mixture was stirred at 50 C. The progress of the reaction was monitored by TLC. Upon completion, the reaction was quenched with water. Ethyl acetate was added to extract the product. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (PE/EA= 30:1-10:1) to afford the desired product 3a in 85% yield as white solid, 196.6 mg. |
71% | With manganese(IV) oxide; potassium hydroxide; In tert-Amyl alcohol; at 120℃; for 21h;Inert atmosphere; | General procedure: Using a nitrogen-filled glove box, an oven-dried Schlenk tube (100mL volume) was charged with a magnetic stirring bar, MnO2 (0.05mmol), KOH (0.5mmol), alcohols (1) (0.55mmol), heteroarenes (2) (0.5mmol) and t-AmOH (1mL). Then the Schlenk tube was closed tightly with a Teflon cap, removed from the glove box. A reflux condenser was evacuated and refilled with dry air and then attached to the Schlenk tube maintaining dry air stream. A bubble counter was attached to the top of the condenser and the whole system was purged with dry air for 15s. The Schlenk tube was immersed into a pre-heated oil bath (design temperature). After design time the reaction was cooled, a small aliquot of the organic phase was analyzed by GC or GC-MS to monitor product formation. Purification of the remainder by column chromatography on silica gel (petroleum ether/ethyl acetate=20/1-5/1) gave the corresponding products in the reported yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With 1H-imidazole; tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 80℃; for 8h; Green chemistry; chemoselective reaction; | General procedure: To a mixture of benzyl alcohol (108 mg, 1.0 mmol) and TBHP(180 mg, 2.0 mmol) in water (3 ml), the catalyst TBAI (73.8 mg,0.2 mmol), imidazole (136 mg, 2.0 mmol), and MeOH (2 ml)were added, and the mixture was stirred at 80 °C for 8 h. Theprogress of the reaction was monitored by TLC. After completionof reaction, the reaction mixture was cooled to room temperature.Then MeOH was distilled out, and the organic productwas extracted with ethyl acetate (3 × 10 ml), repeatedly washedwith distilled water (4 × 5 ml) to remove the unreacted TBHP,dried with anhydrous sodium sulfate, and the solvent was evaporatedunder reduced pressure to afford methyl benzoate (112mg, yield 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With lithium bromide monohydrate; [bis(acetoxy)iodo]benzene; In 2,2,2-trifluoroethanol; at 20℃; for 0.166667h; | General procedure: To a solution of alkoxybenzylalcohol 1 (0.2 mmol) in CF3CH2OH (1 mL) were added LiBr·H2O (0.6 mmol) and PhI(OAc)2 (0.6 mmol) atroom temperature. After completion of the reaction as indicated by TLC monitoring, saturated aq. Na2SO3 wasadded and the mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, driedover anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford pure dibrominated compounds 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.3%; 80.7% | With ammonium hydroxide; manganese(IV) oxide; oxygen; at 130℃; under 11251.1 Torr; for 30h;Autoclave; | General procedure: The ammoxidation of alcohols and hydration of nitrileswere performed in a high-pressure steel autoclave reactorequipped with a PTFE bottle, magnetic stirrer (900 rpm), andan explosion-proof pressure sensor. For the ammoxidation ofalcohols, the as-prepared catalyst, aqueous ammonia(28%-30% NH3), and alcohols were added into a certainamount of t-amyl alcohol solvent in the reactor, then the autoclavewas sealed and purged with oxygen for two times to excludethe inside air. For the hydration of nitrile, the as-preparedcatalyst, nitrile, and water were added into a certain amount oft-amyl alcohol solvent in the reactor, then the autoclave wassealed and purged with N2 for two times to exclude the insideair. After that, the reactor was quickly heated to the desiredtemperature (the reaction temperature was measured by athermocouple in the autoclave) in an oil bath. After a desiredreaction time, the reactor was placed in an ice bath to quenchthe reaction. After separation of the solid catalyst by centrifugation,the liquid was analyzed with a Shimadzu GC-2014 gaschromatograph equipped with a flame ionization detector(FID) and an Agilent HP-6890 gas chromatograph-mass spectrometer,with ethylbenzene, bromobenzene, hexadecane, orbiphenyl used as internal standards. The gas-phase products,such as CO and CO2, were analyzed with a Fu Li-9790 gaschromatograph equipped with a thermal conductivity detector(TCD). Notably, no CO and CO2 signals were observed in TCDand total carbon balances were always >90.0% in this work.Safety Note: The high-pressure oxygen has been extensivelyused in the aerobic oxidations [21,22], and the reaction systemsin this work were out of the explosion limits of the reactants.For example, the explosion limit of benzyl alcohol is1.3%-13.0% in oxygen, and the concentration of benzyl alcoholin the gaseous phase in this work is in a 0-0.4% region, whichis out of the explosion limits. Furthermore, the fire and staticelectricity are not allowed to access the internal reactor forsafety reasons. In the kinetics study, the average reaction rateswere calculated from the moles of substrate converted pergram of catalyst in one hour (mmol gcat-1 h-1), with the conversionof substrate controlled to be lower than 20.0%. |
Tags: 612-16-8 synthesis path| 612-16-8 SDS| 612-16-8 COA| 612-16-8 purity| 612-16-8 application| 612-16-8 NMR| 612-16-8 COA| 612-16-8 structure
[ 119138-29-3 ]
4-(Hydroxymethyl)-3-methoxyphenol
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[ 135362-69-5 ]
3-((4-Methoxybenzyl)oxy)propan-1-ol
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[ 119138-29-3 ]
4-(Hydroxymethyl)-3-methoxyphenol
Similarity: 0.97
[ 135362-69-5 ]
3-((4-Methoxybenzyl)oxy)propan-1-ol
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[ 119138-29-3 ]
4-(Hydroxymethyl)-3-methoxyphenol
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[ 135362-69-5 ]
3-((4-Methoxybenzyl)oxy)propan-1-ol
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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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