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[ CAS No. 73875-27-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 73875-27-1
Chemical Structure| 73875-27-1
Chemical Structure| 73875-27-1
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Product Details of [ 73875-27-1 ]

CAS No. :73875-27-1 MDL No. :MFCD08458461
Formula : C11H15BrO4 Boiling Point : -
Linear Structure Formula :- InChI Key :FQPOTLCIUAYGPN-UHFFFAOYSA-N
M.W : 291.14 Pubchem ID :12560769
Synonyms :

Calculated chemistry of [ 73875-27-1 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 65.08
TPSA : 36.92 Ų

Pharmacokinetics

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) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.24
Log Po/w (XLOGP3) : 2.86
Log Po/w (WLOGP) : 2.79
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 3.07
Consensus Log Po/w : 2.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.46
Solubility : 0.101 mg/ml ; 0.000346 mol/l
Class : Soluble
Log S (Ali) : -3.29
Solubility : 0.148 mg/ml ; 0.000508 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.021 mg/ml ; 0.0000723 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.15

Safety of [ 73875-27-1 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 73875-27-1 ]

* 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 [ 73875-27-1 ]

[ 73875-27-1 ] Synthesis Path-Downstream   1~49

  • 1
  • [ 6138-90-5 ]
  • [ 73875-27-1 ]
  • [ 83036-57-1 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 2,3,4,5-tetramethoxy-6-methyl-1-bromobenzene With n-butyllithium; copper(I) bromide dimethylsulfide complex In diethyl ether; hexane at 0℃; for 3h; Stage #2: trans-geranyl bromide In diethyl ether; hexane at 0 - 20℃; for 5h;
Yield given. Multistep reaction;
With n-butyllithium; copper(I) bromide 1) THF, hexane, -50 deg C, 5 min; 2) THF, hexane, -50 deg C; 3) THF, hexane, room temperature, 2 h; Multistep reaction;
  • 2
  • [ 59277-17-7 ]
  • [ 73875-27-1 ]
  • [ 73875-21-5 ]
YieldReaction ConditionsOperation in experiment
With magnesium; copper(I) bromide 1.) THF, 2.) THF, 0 deg C, 2h; Yield given. Multistep reaction;
  • 3
  • [ 35896-58-3 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
100% With dihydrogen peroxide; acetic acid; sodium bromide; In water; at 20 - 40℃; for 1.08333h; 2,3,4,5-Tetramethoxytoluene 3 (2.1 g, 10 mmol) and NaBr (1.1 g, 10 mmol) were dissolved in AcOH (5 mL), a solution of 30% H2O2 (1.2 mL, 10 mmol) was added dropwise over 5 min at room temperature. The mixture was stirred and heated at 40 C for 1 h and quenched with H2O( 5 mL) and extracted with diethyl ether (3 × 30 mL). The combined organic phases were washed with saturated NaHCO3(3 × 10 mL) until pH 7, then dried over anhydrous Na2SO4,and evaporated under reduced pressure to give yellow oil 4 (2.9 g) in quantatitive yield. 1H NMR (400 MHz, CDCl3) delta 3.92 (s, 3H, OCH3), 3.91(s, 3H, OCH3), 3.85 (s, 3H, OCH3), 3.79 (s, 3H, OCH3),2.30 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3)delta 148.3, 147.2, 146.3,145.5, 127.3, 114.3, 61.4 (OCH3), 61.1 (OCH3), 60.9(OCH3), 60.8 (OCH3), 15.9 (CH3). GC-MS (EI): m/z = 290.
91% With bromine; In dichloromethane; at 20℃; for 1h; Step 3a: Synthesis of 1-Bromo-2,3,4,5-tetramethoxy-6-methyl benzeneTo a stirred solution of l,2,3,4-tetramethoxy-5-methylbenzene (obtained in Step 2a) (1.60 g, 7.54 mmol) in DCM (50 mL), a solution of bromine (0.41 mL, 7.92 mmol) in DCM (15 mL) was slowly added, and the resulting mixture was stirred at room temperature for 1 h. Water was added, the organic layer was separated and washed with 1 M NaOH and brine. The combined organic layers were dried over sodium sulphate and concentrated to dryness to give the product as yellow oil (2.00 g, 91%).Yield: 91%. TLC: R/= 0.80 petroleum ether:EtOAc 90:10 v/v. Spectroscopic data were as those reported in the literature by Tremblay, M. S. et al, Org. Lett. 2005, 7, 2417
With bromine; In dichloromethane; at 10 - 20℃; for 2h;Product distribution / selectivity; EXAMPLE 3Preparation of Grignard Reagent of 2,3,4,5 tetramethoxy-6-methyl-bromobenzene Compound of Formula IIc 2,3dimethoxy-5-methyl 1,4 benzoquinone compound of formula 2, 2.5 g was dissolved in 7.5 ml of methylene dichloride and treated with sodium hydrosulphite (3.56 g) in alkaline solution at 10-20 C. After 2 hours the reaction mixture was treated with conc. HCl (3.4 ml) to acidic pH. The reaction mixture was extracted with methylene dichloride and washed with water. The organic solvent was concentrated and poured in hexane. The precipitated solid was filtered to obtain 2.25 g. of 2,3 dimethoxy 5 methyl 1,4 hydroquinone compound of formula 4. The solid was taken in alkaline solution and dimethyl sulphate (5.75 g) was added at 40-50 C. The reaction mixture was quenched after 4 hours in water and extracted in methylene dichloride. The solvent was evaporated and the crude obtained was distilled under vacuum at 80 C. at 0.5-1.0 mm Hg to obtain 2.33 g of 2,3,4,5-tetramethoxy toluene. The compound was taken in methylene dichloride (15 ml) and treated with bromine (1.75 g) at 10-20 C. The reaction was quenched in water after 2 hours and extracted in methylene dichloride. The methylene dichloride was evaporated. The concentrated mass was added to hexane to precipitate out the solid of 2,3,4,5-tetramethoxy-6-methyl bromobenzene (3.03 g) of formula 14b. The compound of formula 14b was reacted with magnesium (0.30 g) in tetrahydrofuran, at ambient temperature, in presence of a pinch of iodine to form the Grignard reagent 2,3,4,5-tetramethoxy-6-methyl bromobenzene of formula IIc.; EXAMPLE 4Preparation of Grignard Reagent of 2,3,4,5 tetramethoxy-6-methyl-bromobenzene Compound of Formula IIc 2,3-dimethoxy 5-methyl-1,4-benzoquinone of formula 2, (2.5 g) was dissolved in 7.5 ml of methylene dichloride and treated with sodium hydrosulphite (3.56 g) in alkaline solution at 10-20 C. After 2 hours the reaction mixture was treated with conc. HCl (3.4 ml) to acidic pH. The reaction mixture was extracted with methylene dichloride and washed with water. The organic solvent was concentrated and poured in hexane. The precipitated solid was filtered to obtain 2.25 g of 2,3-dimethoxy-5-methyl-1,4-hydroquinone of formula 4. The solid was taken in acetone, potassium carbonate (6.3 g) and dimethyl sulphate (5.75) g were added at 40-50 C. The reaction mixture was quenched after 4 hours in water and extracted in methylene dichloride. The solvent was evaporated and the crude obtained was distilled under vacuum at 80 C. at 0.5-1.0 mm Hg to obtain 2.33 g of 2,3,4,5-tetramethoxy toluene. The compound was taken in methylene dichloride (15 ml) and treated with bromine (1.75 g) at 10-20 C. The reaction was quenched in water after 2 hours and extracted in methylene dichloride. The methylene dichloride was evaporated. The concentrated mass was added to hexane to precipitate out the solid of 2,3,4,5-tetramethoxy-6-methyl-bromobenzene (3.03 g), compound of formula 14b. The compound 14b was reacted with magnesium (0.30 g) in tetrahydrofuran, at ambient temperature, in presence of a pinch of iodine to form the Grignard reagent of 2,3,4,5 tetramethoxy-6-methyl bromobenzene compound of the formula IIc.
  • 4
  • [ 73875-27-1 ]
  • [ 106-95-6 ]
  • [ 71573-66-5 ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: 2,3,4,5-tetramethoxy-6-methyl-1-bromobenzene With iodine; magnesium In tetrahydrofuran at 45℃; for 0.75h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 3h; 10.4 Step 4: Synthesis of 1-Allyl-2,3,4,5-tetramethoxy-6-methyl benzene Step 4: Synthesis of 1-Allyl-2,3,4,5-tetramethoxy-6-methyl benzeneA three-neck round-bottomed flask equipped with a reflux condenser and a dropping funnel under a nitrogen atmosphere was charged with dry THF (5 mL) and dry Mg turnings (250 mg, 10.3 mmol). Iodine (1 mg) was added, the stirred suspension was warmed to 45°C and a solution of l-bromo-2,3,4,5-tetramethoxy-6-methylbenzene (obtained in Step 3a) (2.00 g, 6.87 mmol) in dry THF (15 mL) was added dropwise over 15 min. The reaction mixture was then stirred at 45°C for 30 min and, after cooling back to room temperature, allyl bromide (1.20 mL, 13.7 mmol) was added. The mixture was stirred at room temperature for 3 h, and a saturated NH4C1 solution was added. The mixture was extracted with EtOAc and washed with water and brine. The combined organic layers were dried over sodium sulphate and concentrated to dryness. Purification by silica gel flash column chromatography eluting with 50:50 v/v petroleum ether:DCM gave the product as a colorless oil (1.17 g, 68%).TLC: R/= 0.80 petroleum ether:EtOAc 90: 10 v/v. Spectroscopic data were as those reported in the literature by Duveaua, D. Y. et al, m Bioorg. Med. Chem. 2010, 18, 6429.
Yield given. Multistep reaction;
With ammonium chloride; magnesium In tetrahydrofuran 19 19 (a) 1-Allyl-2,3,4,5-tetramethoxy-6-methylbenzene 19 (a) 1-Allyl-2,3,4,5-tetramethoxy-6-methylbenzene A catalytic amount of iodine was added to a suspension of 975 mg of magnesium in 20 ml of tetrahydrofuran, and the resulting mixture was warmed up to about 45° C. to give rise to a white turbidity. A solution of 10.61 g of 2,3,4,5-tetramethoxy-6-methylbromobenzene in 30 ml of tetrahydrofuran was then added to the mixture, after which it was heated at about 45° C. for several minutes. The mixture was then stirred at room temperature for 30 minutes, after which 3.47 ml of allyl bromide were added dropwise to the mixture; it was then stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was mixed with a saturated aqueous solution of ammonium chloride and then extracted with ethyl acetate. The solvent was removed from the extract by distillation under reduced pressure, and the residue thus obtained was purified by column chromatography through silica gel, using a 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 7.98 g of the title compound as an oil. Nuclear Magnetic Resonance Spectrum (CDCl3) δ ppm: (only the signals due to an allyl group are reported)
With ammonium chloride; magnesium In tetrahydrofuran 10.a 10(a) 10(a) 1-Allyl-2,3,4,5-tetramethoxy-6-methylbenzene A catalytic amount of iodine was added to a suspension of 975 mg of magnesium in 20 ml of tetrahydrofuran, and the resulting mixture was warmed up to about 45°C to give rise to a white turbidity. A solution of 10.61 g of 2,3,4,5-tetramethoxy-6-methylbromobenzene in 30 ml of tetrahydrofuran was then added to the mixture, after which it was heated at about 45°C for several minutes. The mixture was then stirred at room temperature for 30 minutes, after which 3.47 ml of allyl bromide were added dropwise to the mixture; it was then stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was mixed with a saturated aqueous solution of ammonium chloride and then extracted with ethyl acetate. The solvent was removed from the extract by distillation under reduced pressure, and the residue thus obtained was purified by column chromatography through silica gel, using a 10: 1 by volume mixture of hexane and ethyl acetate as the eluent, to give 7.98 g of the title compound as an oil.

  • 5
  • [ 73875-27-1 ]
  • [ 98-80-6 ]
  • [ 842162-30-5 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In benzene
  • 6
  • [ 73875-27-1 ]
  • [ 857674-55-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3,4,5-tetramethoxy-6-methyl-1-bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 20h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 0℃;
  • 7
  • [ 605-94-7 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SnCl2; aq. HCl / ethanol 2: 990 mg / aq. KOH / 1 h / 80 °C 3: 84 percent / Br2 / CH2Cl2 / 0.08 h / 3 - 5 °C
Multi-step reaction with 3 steps 1: H2 / Pd/C / methanol / 1551.44 - 2327.17 Torr 2: NaOH / methanol 3: NBS / CH2Cl2
  • 8
  • [ 3066-90-8 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 990 mg / aq. KOH / 1 h / 80 °C 2: 84 percent / Br2 / CH2Cl2 / 0.08 h / 3 - 5 °C
Multi-step reaction with 2 steps 1: NaOH / methanol 2: NBS / CH2Cl2
  • 9
  • [ 73875-27-1 ]
  • 4-methyl-6-(2-methyl-3,4,5,6-tetramethoxyphenyl)hex-4-enal [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C 3.1: 78 percent / K2CO3 / methanol / 16 h / 20 °C 4.1: 85 percent / periodic acid / diethyl ether; tetrahydrofuran / 1.5 h / 20 °C
  • 10
  • [ 73875-27-1 ]
  • 4-methyl-6-(3-methyl-5,6-dimethoxy-1,4-benzoquinon-2-yl)hex-4-enyl hydrogen succinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C 3.1: 78 percent / K2CO3 / methanol / 16 h / 20 °C 4.1: 85 percent / periodic acid / diethyl ether; tetrahydrofuran / 1.5 h / 20 °C 5.1: 74 percent / NaBH4 / methanol / 0.33 h / 0 - 20 °C 6.1: 37 percent / Et3N; N,N-dimethylaminopyridine / CH2Cl2 / 16 h / 20 °C 7.1: 90 percent / aq. cerric ammonium nitrate / acetonitrile / 0.5 h / 0 - 20 °C
  • 11
  • [ 73875-27-1 ]
  • 4-methyl-6-(2-methyl-3,4,5,6-tetramethoxyphenyl)hex-4-enyl hydrogen succinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C 3.1: 78 percent / K2CO3 / methanol / 16 h / 20 °C 4.1: 85 percent / periodic acid / diethyl ether; tetrahydrofuran / 1.5 h / 20 °C 5.1: 74 percent / NaBH4 / methanol / 0.33 h / 0 - 20 °C 6.1: 37 percent / Et3N; N,N-dimethylaminopyridine / CH2Cl2 / 16 h / 20 °C
  • 12
  • [ 73875-27-1 ]
  • methyl 2-acetylamino-6-[4-methyl-6-(3-methyl-5,6-dimethoxy-1,4-benzoquinon-2-yl)hex-4-enoylamino]hexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C 3.1: 78 percent / K2CO3 / methanol / 16 h / 20 °C 4.1: 85 percent / periodic acid / diethyl ether; tetrahydrofuran / 1.5 h / 20 °C 5.1: 78 percent / AgNO3; aq. NaOH / ethanol / 16 h / 20 °C 6.1: 55 percent / aq. cerric ammonium nitrate / acetonitrile / 0.5 h / 0 - 20 °C 7.1: 63 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole hydrate; diisopropylethylamine / CH2Cl2 / 16 h / 20 °C
  • 13
  • [ 73875-27-1 ]
  • methyl 2-(2-acetylamino-acetylamino)-6-[4-methyl-6-(3-methyl-5,6-dimethoxy-1,4-benzoquinon-2-yl)hex-4-enoylamino]hexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C 3.1: 78 percent / K2CO3 / methanol / 16 h / 20 °C 4.1: 85 percent / periodic acid / diethyl ether; tetrahydrofuran / 1.5 h / 20 °C 5.1: 78 percent / AgNO3; aq. NaOH / ethanol / 16 h / 20 °C 6.1: 55 percent / aq. cerric ammonium nitrate / acetonitrile / 0.5 h / 0 - 20 °C 7.1: 34 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole hydrate; diisopropylethylamine / CH2Cl2 / 16 h / 20 °C
  • 14
  • [ 73875-27-1 ]
  • [ 26539-07-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C 3.1: 78 percent / K2CO3 / methanol / 16 h / 20 °C 4.1: 85 percent / periodic acid / diethyl ether; tetrahydrofuran / 1.5 h / 20 °C 5.1: 78 percent / AgNO3; aq. NaOH / ethanol / 16 h / 20 °C 6.1: 55 percent / aq. cerric ammonium nitrate / acetonitrile / 0.5 h / 0 - 20 °C
  • 15
  • [ 73875-27-1 ]
  • [ 85228-79-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C 3.1: 78 percent / K2CO3 / methanol / 16 h / 20 °C
  • 16
  • [ 73875-27-1 ]
  • [ 85216-20-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C 3.1: 78 percent / K2CO3 / methanol / 16 h / 20 °C 4.1: 85 percent / periodic acid / diethyl ether; tetrahydrofuran / 1.5 h / 20 °C 5.1: 74 percent / NaBH4 / methanol / 0.33 h / 0 - 20 °C
  • 17
  • [ 73875-27-1 ]
  • [ 99348-11-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C 3.1: 78 percent / K2CO3 / methanol / 16 h / 20 °C 4.1: 85 percent / periodic acid / diethyl ether; tetrahydrofuran / 1.5 h / 20 °C 5.1: 78 percent / AgNO3; aq. NaOH / ethanol / 16 h / 20 °C
  • 18
  • [ 73875-27-1 ]
  • [ 849034-07-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: nBuLi; CuBr*Me2S / diethyl ether; hexane / 3 h / 0 °C 1.2: 48 percent / diethyl ether; hexane / 5 h / 0 - 20 °C 2.1: 65 percent / aq. NBS / tetrahydrofuran / 3 h / 20 °C
  • 19
  • [ 150626-26-9 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / acetone / 6 h / Heating 2: 2.05 g / N-bromosuccinimide / CH2Cl2 / 2 h / 20 °C
  • 20
  • [ 106-44-5 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 88 percent / Fe; Br2 / CHCl3 / 4 h / 20 °C 2: 66 percent / CuCN; Me2CO3 / 1,2-dimethoxy-ethane; methanol / 120 h / 80 °C 3: K2CO3 / acetone / 6 h / Heating 4: 2.05 g / N-bromosuccinimide / CH2Cl2 / 2 h / 20 °C
  • 21
  • [ 36776-51-9 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 66 percent / CuCN; Me2CO3 / 1,2-dimethoxy-ethane; methanol / 120 h / 80 °C 2: K2CO3 / acetone / 6 h / Heating 3: 2.05 g / N-bromosuccinimide / CH2Cl2 / 2 h / 20 °C
  • 22
  • [ 73875-27-1 ]
  • [ 857674-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 1.2: B(OMe)3 / tetrahydrofuran; hexane / 20 h / -78 - 20 °C 1.3: aq. HCl / tetrahydrofuran; hexane / 0 °C 2.1: 66 percent / K3PO4; DPEPhos / Pd2dba3 / toluene / 24 h / 110 °C 3.1: 68 percent / cerric ammonium nitrate / acetonitrile; H2O / 1 h / 0 - 20 °C
  • 23
  • [ 73875-27-1 ]
  • [ 857674-71-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 1.2: B(OMe)3 / tetrahydrofuran; hexane / 20 h / -78 - 20 °C 1.3: aq. HCl / tetrahydrofuran; hexane / 0 °C 2.1: 66 percent / K3PO4; DPEPhos / Pd2dba3 / toluene / 24 h / 110 °C 3.1: 68 percent / cerric ammonium nitrate / acetonitrile; H2O / 1 h / 0 - 20 °C 4.1: H2 / Pd/C / CDCl3
  • 24
  • [ 73875-27-1 ]
  • [ 857674-59-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 1.2: B(OMe)3 / tetrahydrofuran; hexane / 20 h / -78 - 20 °C 1.3: aq. HCl / tetrahydrofuran; hexane / 0 °C 2.1: 66 percent / K3PO4; DPEPhos / Pd2dba3 / toluene / 24 h / 110 °C
  • 25
  • [ 73875-27-1 ]
  • 2,3-dimethoxy-5-methyl-6-phenylcyclohexa-2,5-diene-1,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Pd(PPh3)4; Na2CO3 / benzene 2: aq. ceric ammonium nitrate / acetonitrile
  • 26
  • [ 21450-56-6 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 92 percent / Br2 / CH2Cl2 / -10 °C 2: 1.) n-BuLi / 1.) Et2O, 30 min, 2.) Et2O, 1 h, low temperature, 10 h, room temperature, 3 h, reflux 3: 83 percent / Br2 / CH2Cl2 / 3 - 5 °C
Multi-step reaction with 3 steps 1: 80 percent / POCl3 / 1.) 144 h, room temperature, 2.) 3 h, 40 deg C 2: 67 percent / conc. HCl, H2, 10percent Pd-C / acetic acid / 120 h 3: 83 percent / Br2 / CH2Cl2 / 3 - 5 °C
  • 28
  • [ 65884-12-0 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 67 percent / conc. HCl, H2, 10percent Pd-C / acetic acid / 120 h 2: 83 percent / Br2 / CH2Cl2 / 3 - 5 °C
  • 30
  • [ 25245-39-0 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) Et2O, 30 min, 2.) Et2O, 1 h, low temperature, 10 h, room temperature, 3 h, reflux 2: 83 percent / Br2 / CH2Cl2 / 3 - 5 °C
  • 31
  • [ 73875-27-1 ]
  • [ 67913-13-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: PTA, CAN / acetonitrile; H2O / 0.33 h
  • 32
  • [ 73875-27-1 ]
  • [ 38658-30-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: PTA, CAN / acetonitrile; H2O / 0.33 h
  • 33
  • 1-benzenesulfonyl)-2-methyl-4-chloro-2-butene [ No CAS ]
  • [ 73875-27-1 ]
  • [ 35896-58-3 ]
YieldReaction ConditionsOperation in experiment
80% With copper(I) bromide; In tetrahydrofuran; EXAMPLE 18 A Grignard reagent was prepared by reacting 14.5 g (50 mmol) of 2,3,4,5-tetramethoxy-6-methyl-1-bromobenzene with 1.6 g (66 mmol) of metallic magnesium, in 120 ml of tetrahydrofuran. The above Grignard reagent was added dropwise at 0 C. over a period of 2 hours to a suspension of 6.1 g (25 mmol) of 1-benzenesulfonyl)-2-methyl-4-chloro-2-butene (trans isomer) and 7.1 g (50 mmol) of cuprous bromide in 100 ml of tetrahydrofuran. After such dropwise addition, stirring was continued at the same temperature for 2 hours to complete the reaction. The reaction mixture was poured into ice water, acidified with acetic acid, and extracted with chloroform. The chloroform layer was washed with water and dried. The solvent was distilled off from the chloroform solution under reduced pressure, and the residue (17.8 g) was purified by silica gel chromatography (developing solvent: chloroform). There were obtained 8.5 g of 2,3,4,5-tetramethoxy-6-methylbenzene as fastest moving component fraction and 8.7 g (80% yield) of the subject compound as later recovered elude.
  • 34
  • [ 14199-15-6 ]
  • [ 73875-27-1 ]
  • methyl 4-(2,3,4,5-tetramethoxy-6-methylbenzyloxy)phenylacetate [ No CAS ]
  • 4-(2,3,4,5-tetramethoxy-6-methylbenzyloxy)phenylacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
R.1.e REFERENCE EXAMPLE 1 (e) Using 1,2,3,4-tetramethoxy-5-methyl-6-bromobenzene and methyl p-hydroxyphenylacetate and following the procedure described above, there were obtained methyl 4-(2,3,4,5-tetramethoxy-6-methylbenzyloxy)phenylacetate (Compound 17) and 4-(2,3,4,5-tetramethoxy-6-methylbenzyloxy)phenylacetic acid (Compound 18).
  • 35
  • [ 73875-27-1 ]
  • [ 7439-95-4 ]
  • [ 918800-77-8 ]
YieldReaction ConditionsOperation in experiment
With iodine In tetrahydrofuran at 20℃; 3; 4 EXAMPLE 3Preparation of Grignard Reagent of 2,3,4,5 tetramethoxy-6-methyl-bromobenzene Compound of Formula IIc 2,3dimethoxy-5-methyl 1,4 benzoquinone compound of formula 2, 2.5 g was dissolved in 7.5 ml of methylene dichloride and treated with sodium hydrosulphite (3.56 g) in alkaline solution at 10-20° C. After 2 hours the reaction mixture was treated with conc. HCl (3.4 ml) to acidic pH. The reaction mixture was extracted with methylene dichloride and washed with water. The organic solvent was concentrated and poured in hexane. The precipitated solid was filtered to obtain 2.25 g. of 2,3 dimethoxy 5 methyl 1,4 hydroquinone compound of formula 4. The solid was taken in alkaline solution and dimethyl sulphate (5.75 g) was added at 40-50° C. The reaction mixture was quenched after 4 hours in water and extracted in methylene dichloride. The solvent was evaporated and the crude obtained was distilled under vacuum at 80° C. at 0.5-1.0 mm Hg to obtain 2.33 g of 2,3,4,5-tetramethoxy toluene. The compound was taken in methylene dichloride (15 ml) and treated with bromine (1.75 g) at 10-20° C. The reaction was quenched in water after 2 hours and extracted in methylene dichloride. The methylene dichloride was evaporated. The concentrated mass was added to hexane to precipitate out the solid of 2,3,4,5-tetramethoxy-6-methyl bromobenzene (3.03 g) of formula 14b. The compound of formula 14b was reacted with magnesium (0.30 g) in tetrahydrofuran, at ambient temperature, in presence of a pinch of iodine to form the Grignard reagent 2,3,4,5-tetramethoxy-6-methyl bromobenzene of formula IIc.; EXAMPLE 4Preparation of Grignard Reagent of 2,3,4,5 tetramethoxy-6-methyl-bromobenzene Compound of Formula IIc 2,3-dimethoxy 5-methyl-1,4-benzoquinone of formula 2, (2.5 g) was dissolved in 7.5 ml of methylene dichloride and treated with sodium hydrosulphite (3.56 g) in alkaline solution at 10-20° C. After 2 hours the reaction mixture was treated with conc. HCl (3.4 ml) to acidic pH. The reaction mixture was extracted with methylene dichloride and washed with water. The organic solvent was concentrated and poured in hexane. The precipitated solid was filtered to obtain 2.25 g of 2,3-dimethoxy-5-methyl-1,4-hydroquinone of formula 4. The solid was taken in acetone, potassium carbonate (6.3 g) and dimethyl sulphate (5.75) g were added at 40-50° C. The reaction mixture was quenched after 4 hours in water and extracted in methylene dichloride. The solvent was evaporated and the crude obtained was distilled under vacuum at 80° C. at 0.5-1.0 mm Hg to obtain 2.33 g of 2,3,4,5-tetramethoxy toluene. The compound was taken in methylene dichloride (15 ml) and treated with bromine (1.75 g) at 10-20° C. The reaction was quenched in water after 2 hours and extracted in methylene dichloride. The methylene dichloride was evaporated. The concentrated mass was added to hexane to precipitate out the solid of 2,3,4,5-tetramethoxy-6-methyl-bromobenzene (3.03 g), compound of formula 14b. The compound 14b was reacted with magnesium (0.30 g) in tetrahydrofuran, at ambient temperature, in presence of a pinch of iodine to form the Grignard reagent of 2,3,4,5 tetramethoxy-6-methyl bromobenzene compound of the formula IIc.
  • 36
  • [ 124-41-4 ]
  • [ 73875-27-1 ]
  • 1,2,3,4,5-pentamethoxy-6-methylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With methanol; Methyl formate; copper(l) chloride at 115℃; for 2h; Autoclave; Green chemistry; Typical procedure for synthesis of 1 (Table 1) General procedure: A Teflon-lined autoclave (25 mL) was charged with MeONa (1.08 g, 20.0 mmol), MeOH (10 mL), CuCl (40 mg, 0.40 mmol), HCOOMe (0.25 mL, 0.97 g/mL, 4.0 mmol), and monohaloarene (10.0 mmol) then heated to 115 °C, with stirring, for 2 h. After completion of the reaction, the reactor was cooled to room temperature. The mixture was stirred for 0.5 h in the open, then concentrated to recover pure MeOH. Diethyl ether (15 mL) and dilute hydrochloric acid (1.6 M, 15 mL) were added to the residue. The mixture separated into two layers, and the aqueous phase was extracted with diethyl ether (15 mL x 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography on silica gel (mobile phase: petroleum ether-ethyl acetate 15:1) to furnish 1 (conversion and selectivity were determined by GC-MS analysis). The purity of the recovered MeOH was measured as more than 99 % by GC, and the water content of the recovered MeOH was measured as less than 0.12 % by use of the Karl Fischer method.
  • 37
  • [ 73875-27-1 ]
  • [ 764723-80-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 0.75 h / 45 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 20 °C / Inert atmosphere; Reflux 2.2: 1 h / 0 °C 2.3: 1 h / 0 °C
  • 38
  • [ 73875-27-1 ]
  • 3-(2,3,4,5-tetramethoxy-6-methylphenyl)propyl-4-(nitrooxy)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 0.75 h / 45 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 20 °C / Inert atmosphere; Reflux 2.2: 1 h / 0 °C 2.3: 1 h / 0 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 4 h / 20 °C
  • 39
  • [ 73875-27-1 ]
  • 3-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)propyl-4-(nitrooxy)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 0.75 h / 45 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 20 °C / Inert atmosphere; Reflux 2.2: 1 h / 0 °C 2.3: 1 h / 0 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 4 h / 20 °C 4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 0 °C
  • 40
  • [ 73875-27-1 ]
  • 3-(2,3,4,5-tetramethoxy-6-methylphenyl)propyl-5-(nitrooxy)pentanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 0.75 h / 45 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 20 °C / Inert atmosphere; Reflux 2.2: 1 h / 0 °C 2.3: 1 h / 0 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 4 h / 20 °C
  • 41
  • [ 73875-27-1 ]
  • 3-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)propyl-5-(nitrooxy)pentanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 0.75 h / 45 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 20 °C / Inert atmosphere; Reflux 2.2: 1 h / 0 °C 2.3: 1 h / 0 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 4 h / 20 °C 4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
  • 42
  • [ 73875-27-1 ]
  • 3-(2,3,4,5-tetramethoxy-6-methylphenyl)propyl-6-(nitrooxy)hexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 0.75 h / 45 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 20 °C / Inert atmosphere; Reflux 2.2: 1 h / 0 °C 2.3: 1 h / 0 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 4 h / 20 °C
  • 43
  • [ 73875-27-1 ]
  • 3-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)propyl-6-(nitrooxy)hexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 0.75 h / 45 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 20 °C / Inert atmosphere; Reflux 2.2: 1 h / 0 °C 2.3: 1 h / 0 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 4 h / 20 °C 4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
  • 44
  • [ 6443-69-2 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dihydrogen peroxide; sodium bromide; acetic acid / water / 1 h / 20 °C 2: copper(I) bromide / methanol / 2 h / 80 °C / Inert atmosphere 3: dihydrogen peroxide; sodium bromide; acetic acid / water / 1.08 h / 20 - 40 °C
  • 45
  • [ 72326-72-8 ]
  • [ 73875-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(I) bromide / methanol / 2 h / 80 °C / Inert atmosphere 2: dihydrogen peroxide; sodium bromide; acetic acid / water / 1.08 h / 20 - 40 °C
  • 46
  • [ 73875-27-1 ]
  • [ 30685-17-7 ]
YieldReaction ConditionsOperation in experiment
90% With ammonium cerium (IV) nitrate In tetrahydrofuran; water at 0 - 20℃; for 0.583333h; 5-Bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone (5) Compound 4 (2.9 g, 10 mmol) was dissolved in THF (10 mL),to the mixture a solution of ammonium ceric nitrate (2.2 g,6 mmol) in H2O (5 mL) was added dropwise over a period of 5 min at 0 °C. The mixture was stirred for another 30 min at room temperature and extracted with dichloromethane (3 × 30 mL). The organic layers were washed with brine (3 × 10 mL) until neutrality, then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by a silica-gel column chromatography with petroleum ether and EtOAc (5:1) to give red needle 5 (2.34 g) in 90% yield. m.p. 68-69 °C. 1H NMR (400 MHz, CDCl3)δ 4.04 (s, 3H, OCH3), 4.01(s, 3H, OCH3), 2.21 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3)δ 181.0 (C=O), 176.7(C=O), 145.2, 144.1, 143.8, 133.6, 61.58 (OCH3), 61.33(OCH3), 16.75 (CH3). GC-MS (EI): m/z = 260.
  • 47
  • [ 73875-27-1 ]
  • methyl (E)-2-methyl-4-(2,3,4,5-tetramethoxy-6-methylphenyl)but-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / N,N-dimethyl-formamide / 4 h / 110 °C / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 40 °C / Inert atmosphere
  • 48
  • [ 73875-27-1 ]
  • [ 94828-31-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / N,N-dimethyl-formamide / 4 h / 110 °C / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 40 °C / Inert atmosphere 3: lithium aluminium tetrahydride / diethyl ether; tetrahydrofuran / 4 h / 0 - 20 °C
  • 49
  • [ 24850-33-7 ]
  • [ 73875-27-1 ]
  • [ 71573-66-5 ]
YieldReaction ConditionsOperation in experiment
75% With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine In N,N-dimethyl-formamide at 110℃; for 4h; Inert atmosphere; 3.5.GeneralProcedureforStilleCoupling General procedure: Bromoaryl(1.0mmol),(PPh3)2PdCl2(0.025mmol)allylSnBu3(1.1mmol),andPPh3(0.1mmol) weredissolvedinDMF(10mL),andthenthemixturewasheatedat110°Cfor4hunderanN2atmosphere.ThereactionmixturewasdilutedwithH2O,extractedfivetimeswithEt2O,andthe combinedextractsweredriedoverNa2SO4andevaporatedundervacuum.Theresiduewaspurified bycolumnchromatographywithsilicagelasthestationaryphase(10%-20%ethylacetate/n-hexane) toyieldthetitularallylatedarene.
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