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[ CAS No. 2103-57-3 ] {[proInfo.proName]}

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Chemical Structure| 2103-57-3
Chemical Structure| 2103-57-3
Structure of 2103-57-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 2103-57-3 ]

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Product Citations

Product Details of [ 2103-57-3 ]

CAS No. :2103-57-3 MDL No. :MFCD00003310
Formula : C10H12O4 Boiling Point : No data available
Linear Structure Formula :(CH3O)3C6H2CHO InChI Key :UCTUXUGXIFRVGX-UHFFFAOYSA-N
M.W : 196.20 Pubchem ID :75006
Synonyms :

Calculated chemistry of [ 2103-57-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.31
TPSA : 44.76 ?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) : -6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 1.3
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 0.55
Log Po/w (SILICOS-IT) : 2.03
Consensus Log Po/w : 1.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.93
Solubility : 2.31 mg/ml ; 0.0118 mol/l
Class : Very soluble
Log S (Ali) : -1.84
Solubility : 2.83 mg/ml ; 0.0144 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.363 mg/ml ; 0.00185 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 2103-57-3 ]

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

Application In Synthesis of [ 2103-57-3 ]

* 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 [ 2103-57-3 ]

[ 2103-57-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 141-78-6 ]
  • [ 2103-57-3 ]
  • [ 33130-04-0 ]
  • 2
  • [ 2103-57-3 ]
  • [ 19676-64-3 ]
YieldReaction ConditionsOperation in experiment
95% With sulfuric acid; dihydrogen peroxide; In methanol; water; at 20℃; for 24h; Synthesis of 2,3,4-trimethoxyphenolA solution of 2,3,4-trimethoxybenzaldehyde (5.0 g, 36.7 mmol) and 31% aqueous H202 (5.3 g,48 mmol) in methanol (50 mL) was stirred with sulfuric acid (0.5 mL) at room temperature for24 h, the reaction was quenched with water, and extracted with CH2C12. The organic layer waswashed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. Theresidue was purified by column chromatography on silica gel with EtOAc/hexane (15:85) toyield a pure product of 2,3,4-trimethoxyphenol (6.3 g, 95% yield). C9H,204 ‘H NMR (400 MHz,CDC13) 6.57 (1 H, d, J= 8.0 Hz), 6.50 (1 H, d, J= 8.0 Hz), 3.87 (3 H, br s), 3.83 (3 H, br s),3.74 (3 H, br s). ‘3C NMR (100 MHz, CDC13) 146.7, 143.3, 142.2, 140.5, 108.7, 107.6, 61.0,60.7, 56.4. HRMS (negative mode) calcd for C9H,,04: 183.0657, found: mlz 183.0661 [M- Hf.
94% With formic acid; dihydrogen peroxide; In dichloromethane; water; at 20℃;Reflux; 2,3,4-trimethoxybenzaldehyde (11.7 g, 59.7 mmol) was dissolved in 200 mL of DCM. H2O2 30% (15.4 mL, 2.5 equiv) and formic acid (9.2 mL, 4 equiv) were added and the solution was stirred and heated to reflux for 6 h. The reaction mixture was then allowed to cool to room temperature and stirred overnight at the same temperature. 1.5 N NaOH (200 mL) was added to the solution, and the mixture was further stirred for 15 min. The organic layer was concentrated under vacuum and the residue was gathered with the aqueous layer. 130 mL of methanol were added, and the mixture was stirred for 30 min at r.t. The methanol was evaporated, and the mixture was extracted with DCM. The crude was purified by column chromatography on silicagel (eluent: petroleum ether/ethyl acetate 7:3) to give 1b (10.3 g, 94%). 1H NMR (500MHz, CDCl3) d: 3.81 (3H, s, OCH3), 3.89 (3H, s, OCH3),3,95 (3H, s, OCH3), 5.40(1H, s, OH), 6.55 (1H, d, J = 10 Hz,CH-5), 6.61 (1H, d, J = 10 Hz, CH-6).13C NMR (500MHz, CDCl3) d:56.6 (OCH3-4), 60.9 (OCH3-3), 61.2 (OCH3-2), 107.6 (CH-5), 108.5 (CH-6), 140.1 (C-2) 142.9(C-1), 145.2 (C-3), 150.4 (C-4); EIMS m/z 184 [M]+ (100), 169 (80), 154 (20), 126 (40); anal. C,58.71; H, 6.62 %, calcd for C9H12 O4 C, 58.69;H, 6.57 %,
79% With sulfuric acid; dihydrogen peroxide; In methanol; at 0 - 20℃; for 0.5h; A solution of 2,3,4-trimethoxybenzaldehyde (20g, 100.9mmol) and sulfuric acid (2mL) in MeOH (200mL) was stirred at 0C. To the previous solution, 30% H2O2 (13.6mL, 131.2mmol) was added dropwise at 0C and then was stirred at room temperature for 30min. The solution was evaporated and extracted with EtOAc. The crude product was purified through chromatography to provide a transparent oil (14.8g, 79%; EtOAc/hexane, Rf=0.25). 1H NMR (300MHz, CDCl3): δ 3.79 (s, 3H), 3.88 (s, 3H), 3.94 (s, 3H), 5.54 (s, 1H), 6.54 (d, 1H, J=9.0Hz), 6.62 (d, 1H, J=9.0Hz).
79% With sulfuric acid; dihydrogen peroxide; In methanol; at 20℃; for 0.5h;Inert atmosphere; 4.1.7 2,3,4-Trimethoxyphenol (15) H2O2 (30%, 13.6 mL, 131.2 mmol) was added dropwise at 0 C to a solution of 2,3,4-trimethoxybenzaldehyde (20 g, 100.9 mmol), and sulfuric acid (2 mL) in MeOH (200 mL) and the resulting mixture was stirred at room temperature for 30 min. The reaction was evaporated and extracted with EtOAc. The organic layer was collected and purified by column chromatography to afford 15 (14.8 g, 79%) as a transparent oil. 1H NMR (300 MHz, CDCl3): δ 3.79 (s, 3H), 3.88 (s, 3H), 3.94 (s, 3H), 5.54 (s, 1H), 6.54 (d, J = 9.0 Hz, 1H), 6.62 (d, J = 9.0 Hz, 1H).
With sulfuric acid; dihydrogen peroxide; In methanol; at 25℃;Inert atmosphere; INTERMEDIATE 12,3,4-Trimethoxyphenol; A solution of 2,3,4-trimethoxybenzaldehyde (1,00 g, 5.10 mmol) and 30 wt/v % hydrogen peroxide (0.672 mL, 6.52 mmol) in cone. H2SO4 (0.102 mL) and MeOH (10.19 niL) was stirred overnight at 25 0C under N2. After this time the mixture was diluted with water (20 mL) and extracted with CH2Cl2 (3 x 30 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 4OM, Si9 -30 niL/min, 100% hexanes for 360 mL, gradient to 50% EtOAc in hexanes over 2088 mL) to afford 2,3,4-trimethoxyphenol, as a colorless oil. R/ = 0.93 (50% EtOAc/hexanes). LCMS calc. = 185.1; found = 185.2 (M+H)+. 1H NMR (600 MHz, CDCl3): δ 6.62 (d, J- 9.0 Hz5 1 H); 6.55 (d, J= 8.9 Hz, 1 H); 5.49 (s, 1 H); 3.94 (s, 3 H); 3.89 (s, 3 H); 3.80 (s, 3 H).
With sulfuric acid; dihydrogen peroxide; In methanol; at 20℃; for 12h; To a solution of 2,3,4-trimethoxybenzaldehyde (1.0 g, 5.1mmol) in MeOH (7.3 mL), 31% H2O2 (0.75 mg, 6.6 mmol)and H2SO4 (0.07 mL) were added at room temperature.After stirring for 12 h at the same temperature, the volatilesolvent was removed in vacuo to leave a residue. Theresidue was treated with H2O (30 mL) and extracted twicewith CHCl3. The extract was washed with H2O, saturatedNaHCO3 aqueous solution, and brine. The organic layerwas dried over Na2SO4 and concentrated in vacuo to givecrude 2,3,4-trimethoxyphenol (1.1 g), which was used forthe next step without further purification.1H NMR (CDCl3; 400 MHz) δ 6.63 (1H, d, J = 9.0 Hz),6.56 (1H, d, J = 9.0 Hz), 5.39 (1H, s), 3.96 (3H, s), 3.90(3H, s), 3.81 (3H, s).
79 g To a solution containing 150.0 g ( 0.77 mol) of 2,3,4-trimethoxybenzaldehyde in 1000 mL of DCM was added 300.0 g (1.74 mol) of m- CPBA in five portions (30 g each) at 0C - 10C (ice-water bath). After the addition the reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was filtered to remove the solid and the filtrate was washed with aqueous NaHC03 (400 mL c 3), water (300 mL) and brine (300 mL). The organic layer was separated and dried over anhydrous Na2S04 and the mixture was filtered. The filtrate was concentrated to provide a dark yellow colored oil which was dissolved in EtOH (600 mL) and treated with a 10% aqueous KOH solution (500 mL) in one portion. The mixture was stirred at 50C for 4 h. The mixture was then cooled and acidified to pH=1 with 1 M HCI and extracted with DCM (500 mL x 3). The combined organic extracts were washed with water (500 mL) and brine (500 mL), dried over anhydrous Na2S04 and then filtered. The filtrate was concentrated and purified by silica gel chromatography (column height: 50 cm, diameter: 20 cm, 100-200 mesh silica gel, petroleum ether / EtOAc = 30/1 , 20/1 , 15/1 , 10/1) to give Int V-1 (79.0 g) as yellow oil. 1H NMR: (CDCIs, 400 MHz): d 6.63 (d, J = 8 Hz, 1 H), 6.55 (d, J = 8 Hz, 1 H), 5.38 (brs, 1 H), 3.96 (s, 3H), 3.90 (s, 3H), 3.81 (s, 3H).
79.0 g Int V-1 To a solution containing 150.0 g (0.77 mol) of 2,3,4-trimethoxybenzaldehyde in 1000 mL of DCM was added 300.0 g (1.74 mol) of m- CPBA in five portions (30 g each) at 0C - 10C (ice-water bath). After the addition the reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was filtered to remove the solid and the filtrate was washed with aqueous NaHC03 (400 mL c 3), water (300 mL) and brine (300 mL). The organic layer was separated and dried over anhydrous Na2S04 and the mixture was filtered. The filtrate was concentrated to provide a dark yellow colored oil which was dissolved in EtOH (600 mL) and treated with a 10% aqueous KOH solution (500 mL) in one portion. The mixture was stirred at 50C for 4 h. The mixture was then cooled and acidified to pH=1 with 1 M HCI and extracted with DCM (500 mL x 3). The combined organic extracts were washed with water (500 mL) and brine (500 mL), dried over anhydrous Na2S04 and then filtered. The filtrate was concentrated and purified by silica gel chromatography (column height: 50 cm, diameter: 20 cm, 100-200 mesh silica gel, petroleum ether / EtOAc = 30/1, 20/1, 15/1, 10/1) to give Int V-1 (79.0 g) as yellow oil. 1H NMR: (CDCIs, 400 MHz): d 6.63 (d, J = 8 Hz, 1H), 6.55 (d, J = 8 Hz, 1H), 5.38 (brs, 1H), 3.96 (s, 3H), 3.90 (s, 3H), 3.81 (s, 3H).

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Technical Information

? Acidity of Phenols ? 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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; ;