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[ CAS No. 66495-88-3 ] {[proInfo.proName]}

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Chemical Structure| 66495-88-3
Chemical Structure| 66495-88-3
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Quality Control of [ 66495-88-3 ]

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Product Details of [ 66495-88-3 ]

CAS No. :66495-88-3 MDL No. :MFCD06656119
Formula : C8H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :GRIWJVSWLJHHEM-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :11804953
Synonyms :

Calculated chemistry of [ 66495-88-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.34
TPSA : 46.53 ?2

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) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 1.0
Log Po/w (WLOGP) : 1.21
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 1.49
Consensus Log Po/w : 1.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.68
Solubility : 3.14 mg/ml ; 0.0207 mol/l
Class : Very soluble
Log S (Ali) : -1.57
Solubility : 4.13 mg/ml ; 0.0272 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.88
Solubility : 2.0 mg/ml ; 0.0132 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 66495-88-3 ]

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 [ 66495-88-3 ]

* 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 [ 66495-88-3 ]

[ 66495-88-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 66495-88-3 ]
  • [ 504-02-9 ]
  • [ 138744-09-9 ]
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  • [ 107-05-1 ]
  • [ 106662-50-4 ]
  • 3
  • [ 24677-78-9 ]
  • [ 74-88-4 ]
  • [ 66495-88-3 ]
YieldReaction ConditionsOperation in experiment
88.8% Reference example 9-1 Preparation for 3-hydroxy-2-methoxybenzaldehyde To a solution of 2,3-hydroxybenzaldehyde (200mg, 1.45mmol) in N,N-dimethylformamide (3.0ml) was added sodium hydride (60.8mg, 1.52mmol) at room temperature, and the mixture was stirred for 1 hour at 50C. The reaction mixture was cooled to room temperature and thereto was added methyl iodide (226mg, 1.60mmol).. The mixture was stirred for 1 hour at 40C and allowed to cool to room temperature, followed by addition of water and extracted with ethyl acetate-toluene (3:1).. The organic layer was washed with water and an aqueous saturated sodium chloride solution in the order, and dried over anhydrous magnesium sulfate.. The solvent was removed under reduced pressure and the residue was recrystallized from hexane to give the subject compound (196mg, 88.8%).1H NMR (CDCl3, 400 MHz) δ 10.27 (s, 1 H), 7.37 (dd, 1 H, J = 1.7 and 7.7 Hz), 7.23 (dd, 1 H, J = 1.7 and 8.0 Hz), 7.15 (m, 1 H), 5.82 (s, 1 H), 3.98 (s, 3 H).. Reference example 9-2
73% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12h;Inert atmosphere; General procedure: To a suspension of substituted 2- or 3-hydroxybenzaldehydes (15, 21, 24, and 27) (1 mmol,1.0 equiv) and K2CO3 (1 mmol, 1 equiv) in anhydrousDMF (6 mL) was added methyl iodide (0.06 mL, 1.0 mmol,1.0 equiv) dropwise under nitrogen atmosphere at room temperature.The mixture was stirred for overnight at room temperature.After completion of the reaction, water (10 mL)was added. The mixture was then extracted with ether(2 × 25 mL), the combined organic layer was washed withbrine (2 × 30 mL), dried over anhydrous Na2SO4, filteredand the filtrate was concentrated in vacuo. The crude residuewas purified by column chromatography (EtOAc/hexane = 1/4) to yield substituted 2- or 3-methoxy benzaldehyde (23, 22,25, and 8) [in case of compound 24, 1.5 equiv of K2CO3 and1.5 equiv of methyl iodide employed].
73% To a stirred solution of 2,3-dihydroxybenzaldehyde (1.00 g, 7.24 mmol) in anhydrous DMF (20 mL) was added K2CO3 (1.00 g, 7.24 mmol) and the mixture was stirred at room temperature for 30 minutes. CH3I (0.54 mL, 8.68 mmol) was then slowly added to the mixture and stirred for 8 hours. After completion of the reaction, it was neutralized by addition of 1N HCl and extracted with ether (3 x 30 mL). The combined organic solvent layers were washed with water (3 x 40 mL), brine (3 x 40 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude was purified by column chromatography (EtOAc: Hexane = 1: 4) To give a white solid compound 10 (0.80 g, 73%).
73% To a stirred solution of 2,3-dihydroxybenzaldehyde (1.00 g, 7.24 mmol) in anhydrous DMF (20 mL) was added K2CO3 (1.00 g, 7.24 mmol) and the mixture was stirred at room temperature for 30 minutes. CH3I (0.54 mL, 8.68 mmol) was then slowly added to the mixture and stirred for 8 hours.After completion of the reaction, it was neutralized with 1N HCl and extracted with ether (3 x 30 mL).The combined organic solvent layers were washed with water (3 x 40 mL), brine (3 x 40 mL), dried over anhydrous Na2SO4 and concentrated in vacuo.The crude compound was purified by column chromatography (EtOAc: Hexane = 1: 4) to give a white solid compound 10 (0.80 g, 73%).
62% A solution of 2, 3-dihydroxybenzaldehyde (10 g, 72 [MMOL)] in anhydrous DMF (100 mL) was treated with K2CO3 (10 g, 72 [MMOL)] at [25C] and the mixture was stirred for 30 minutes. [LODOMETHANE] (4.9 mL, 80 [MMOL)] was added and the reaction was further stirred for 20 h. The reaction was quenched with water and extracted with diethyl ether. The organic layer was dried using sodium sulfate and solvents were evaporated under vacuum. The residue was purified by Biotage to obtain 3-hydroxy-2- [METHOXYBENZALDEHYDE] (6.8 g, 45 mmol, 62%) as a white [SOLID.'H] NMR [(CDC ! S) 5] 4.0 (s, 3H), 5.9 (s, [1H),] 7.2 (m, 2H), 7.4 (m, 1H), 10.3 (s, [1H)] ; GC/MS (ES) 153 [(M+1) +.]
57% A solution of 2,3-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (10 mL) was treated with K2CO3 (1.0 g, 7.24 mmol) and the mixture was stirred at rt for 30 min. Iodomethane (0.50 ml, 7.96 mmol) was added and the reaction was further stirred for 20 h. The reaction was quenched with H2O and extracted with Et2O. The organic layer was dried over Na2SO4 and concentrated. The residue was purified flash column chromatography to afford the title compound (0.63 g, 57%) as a colorless needle.1H NMR δ (CDCl3) 10.28 (1H, s), 7.39 (1H, dd, J=7.8 Hz, 1.8 Hz), 7.25 (1H, dd, J=7.8 Hz, 1.8 Hz), 7.17 (1H, t, J=7.8 Hz), 5.81 (1H, s), 3.99 (1H, s)ESI-MS [M+H]+: 153
45% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h; General procedure: The compound of Formula (VI) is synthesized as shown in the following scheme:
40% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 20h; Reference Example 52 3-hydroxy-2-methoxybenzaldehyde; [Show Image] To a solution (80 mL) of 2,3-dihydroxybenzaldehyde (5.00 g) in N,N-dimethylformamide were added potassium carbonate (4.93 g) and a solution (20 mL) of iodomethane (6.89 g) in N,N-dimethylformamide, and the mixture was stirred at room temperature for 20 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=100:0→60:40) to give the title compound as a white solid (yield: 2.16 g, 40%). 1H-NMR (CDCl3, 300 MHz):δ3.98 (3H, s), 5.83 (1H, s), 7.15 (1H, dd, J = 8 . 1, 7.7 Hz), 7 . 24 (1H, dd, J = 8.1, 1.8 Hz), 7.38 (1H, dd, J = 7.6, 1.8 Hz), 10.27 (1H, s).
[0308] 2,3-dihydroxybenzaldehyde (27.6 g) (200 mmol) is mixed with dry DMF (460 mL) and KHCO3 (80 g, 800 mmol), under N2 atmosphere. The mixture is stirred at room temperature for 30 min. MeI (51 mL, 820 mmol) is added in one portion. The mixture is further stirred at room temperature for 30 h. The excess MeI is evaporated in vacuo. H2O (1.1 L) is added, followed by 37% HCl (46 mL) to reach pH ~3.5 after the addition. The mixture is extracted with Et2O (4x0.55 L then 1x0.28 L). The combined organic layer is further washed with saturated NH4Cl (2x0.35 L), then brine (1x0.7 L), dried on MgSO4, filtered and evaporated in vacuo to yield the crude desired product. This crude is dissolved in Et2O (0.7 L), and extracted with 1M NaOH (2x0.42 L). The combined aqueous layer is treated with 37% HCl (71 mL) to reach pH ~ 1. The resulting suspension is cooled to 15C, filtered on a Buchner filter, the solid is washed with H2O (2x30 mL), dried under suction and then in vacuo at 42C to yield the desired product.

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  • [ 24677-78-9 ]
  • [ 74-88-4 ]
  • [ 66495-88-3 ]
  • [ 86-51-1 ]
YieldReaction ConditionsOperation in experiment
57%; 19% To a stirred solution of 2,3-dihydroxybenzaldehyde (2.0 g, 14.48 mmol) in DMF (25 mL) was added potassium carbonate (2.2 g, 15.90 mmol). The mixture was stirred 30 minutes at room temperature and iodomethane (1.0 mL, 15.90 mmol) was added dropwise. The resulting solution was stirred at room temperature for 18 h. The mixture was hydrolyzed with a saturated aqueous solution of NH4Cl, extracted using ethyl acetate, the organics were washed with brine, dried over MgSCL and concentrated in vacuo before purification by silica gel flash chromatography eluting with a gradient of cyclohexane:ethyl acetate - 100:0 to 75:25 to give as the first eluting compound 2,3-dimethoxy-benzaldehyde as a colorless gum (450 mg, 19% yield) and as the last eluting compound 2-methoxy-3-methyl- benzaldehyde as a white solid (1.27 g, 57% yield). 2,3-dimethoxy-benzaldehyde: 1 H NMR (300MHz, CHCb-d) 10.43 (s, 1H), 7.45-7.38 (m, 1H), 7.18-7.10 (m, 2H), 3.98 (s, 3H), 3.91 (s, 3H). 2-methoxy-3-methyl-benzaldehyde: 1 H NMR (300MHz, CHCb-d) 10.26 (s, 1H), 7.45-7.38 (dd, / = 1.8 and 7.6 Hz, 1H), 7.26-7.10 (m, 2H), 5.79 (s, 1H), 3.97 (s, 3H).
57%; 19% To a stirred solution of 2,3-dihydroxybenzaldehyde (2.0 g, 14.48 mmol) in DMF (25 mL) was added potassium carbonate (2.2 g, 15.90 mmol). The mixture was stirred 30 minutes at room temperature and iodomethane (1.0 mL, 15.90 mmol) was added dropwise. The resulting solution was stirred at room temperature for 18 h. The mixture was hydrolyzed with a saturated aqueous solution of NH4Cl, extracted using ethyl acetate, the organics were washed with brine, dried over MgSC and concentrated in vacuo before purification by silica gel flash chromatography eluting with a gradient of cyclohexane:ethyl acetate - 100:0 to 75:25 to give as the first eluting compound 2,3-dimethoxy-benzaldehyde as a colorless gum (450 mg, 19% yield) and as the last eluting compound 2-methoxy-3-methyl- benzaldehyde as a white solid (1.27 g, 57% yield). 2,3-dimethoxy-benzaldehyde: 1 H NMR (300MHz, CHCb-d) 10.43 (s, 1H), 7.45-7.38 (m, 1H), 7.18-7.10 (m, 2H), 3.98 (s, 3H), 3.91 (s, 3H). 2-methoxy-3 -methyl -benzaldehyde: 1 H NMR (300MHz, CHCh-d) 10.26 (s, 1H), 7.45-7.38 (dd, / = 1.8 and 7.6 Hz, 1H), 7.26-7.10 (m, 2H), 5.79 (s, 1H), 3.97 (s, 3H).
  • 5
  • [ 66495-88-3 ]
  • [ 75-26-3 ]
  • [ 218903-24-3 ]
  • 7
  • [ 66495-88-3 ]
  • [ 107-30-2 ]
  • 2-methoxy-3-(methoxymethyl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
34.1% With potassium carbonate; In tetrahydrofuran; at 60℃; for 11h; Preparation for 2-methoxy-3-(methoxymethoxy)benzaldehyde To a solution of the compound (5.98g, 39.3mmol) of Reference example 9-1 in tetrahydrofuran (200ml) were added potassium carbonate (8.15g, 59.0mmol) and chloromethyl methyl ether (6.33g, 78.6mmol) and the mixture was stirred for 11 hours at 60C. The precipitate was filtered off and the solvent was removed from the filtrate.. To the residue was added water and the mixture was extracted with ethyl acetate.. The organic layer was washed with water and an aqueous saturated sodium chloride solution in the order, and dried over anhydrous magnesium sulfate.. The solvent was removed under reduced pressure and the residue was purified with silica gel chromatography (hexane:ethyl acetate=4:1) to give the subject compound (2.63g, 34.1%).1H NMR (CDCl3, 400 MHz) δ 10.42 (s, 1 H), 7.49 (d, 1 H, J = 7.8 Hz), 7.40 (d, 1 H, J = 8.1 Hz), 7.12 (m, 1 H)), 5.26 (s, 2 H), 4.01 (s, 3 H), 3.53 (s, 3 H).
  • 8
  • [ 66495-88-3 ]
  • [ 18162-48-6 ]
  • 3-[(tert-butyldimethylsilyl)oxy]-2-methoxybenzaldehyde [ No CAS ]
  • 9
  • [ 66495-88-3 ]
  • [ 100-39-0 ]
  • [ 273200-57-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;potassium iodide; In DMF (N,N-dimethyl-formamide); at 20℃; for 17h; To a solution of the compound (11.4 g) obtained in the aforementioned (1), potassium carbonate (22.8 g) and potassium iodide (2.49 g) in DMF (130 ml) was added benzyl bromide (9.8 ml), and the mixture was stirred at room temperature for 17 hrs. The obtained reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate (1500 ml) and water (1500 ml). The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and crystallized from diisopropyl ether and hexane to give 3-benzyloxy-2-methoxybenzaldehyde (13.7 g) as pale-yellow crystals. 1H-NMR (CDCl3) δ:4.03 (3H, s), 5.16 (2H, s), 7.09-7.47 (8H, m), 10.45 (1H, d, J = 0.66 Hz).
With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20℃; for 17h; Reference Example 2 3-Benzyloxy-2-methoxybenzaldehyde To a solution of the compound obtained in Reference Example 1 (11.4 g), potassium carbonate (22.8 g) and potassium iodide (2.49 g) in DMF (130 ml) was added benzyl bromide (9.8 ml), and the mixture was stirred at room temperature for 17 hours. The resulting reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate (1500 ml) and water (1500 ml). The organic layer was washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, and crystallized using diisopropyl ether and hexane to obtain the title compound (13.7 g) as a pale yellow crystal. 1H-NMR (CDCl3) δ: 4.03 (3H, s), 5.16 (2H, s), 7.09-7.47 (8H, m), 10.45 (1H, d, J = 0.66 Hz).
With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 2.5h;Inert atmosphere; [0309] Int60 (17 g, 111 mmol) is mixed with dry DMF (280 mL) and K2CO3 (23 g, 167 mmol), under N2 atmosphere. Benzyl bromide (16.5 mL, 139 mmol) is added in one portion. The mixture is stirred at 40C for 2.5 h, cooled to room temperature and treated with H2O (0.5 L) and toluene (0.5 L). The resulting layers are separated, and the aqueous layer is extracted again with toluene (0.25 L). The combined organic layer is washed with 3x0.25 L H2O, dried on Na2SO4, filtered and evaporated in vacuo. The residue is treated with light petroleum ether (100 mL) and stirred until powdery. The suspension is filtered on Buchner, the solid is washed with light petroleum ether (50 mL), dried under suction and then in vacuo at 40C to yield the desired product.
  • 10
  • [ 66495-88-3 ]
  • 3-bromo-4-hydroxy-5-methoxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
420 mg With N-Bromosuccinimide; In dichloromethane; at 25℃; for 16h; To a solution of 3-hydroxy-2-methoxy-benzaldehyde (0.32 g, compound AF-1) in dry DCM (25 mL) was added N-bromosuccinimide (0.45 g). After being stirred at 25 C for 16 hrs, the reaction mixture was diluted with DCM (25 mL), washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (eluting with EtOAc/PE = 1/4) to give 4-bromo-3-hydroxy-2- methoxy-benzaldehyde (420 mg, Intermediate AF) as a white solid. MS obsd. (ESI+): 231.0[(M+H)+], 233.0 [(M+2+H)+] .
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Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Halogenation of Phenols ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nomenclature of Ethers ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Ethers ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Ethers ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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; ;