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[ CAS No. 151-10-0 ] {[proInfo.proName]}

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Chemical Structure| 151-10-0
Chemical Structure| 151-10-0
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Quality Control of [ 151-10-0 ]

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Product Details of [ 151-10-0 ]

CAS No. :151-10-0 MDL No. :MFCD00008384
Formula : C8H10O2 Boiling Point : -
Linear Structure Formula :(CH3O)2(C6H4) InChI Key :DPZNOMCNRMUKPS-UHFFFAOYSA-N
M.W : 138.16 Pubchem ID :9025
Synonyms :
Resorcinol dimethyl ether

Calculated chemistry of [ 151-10-0 ]      Expand+

Physicochemical Properties

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 : 0.0
Molar Refractivity : 39.43
TPSA : 18.46 ?2

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) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 1.7
Log Po/w (MLOGP) : 1.48
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 1.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.549 mg/ml ; 0.00397 mol/l
Class : Soluble
Log S (Ali) : -2.23
Solubility : 0.81 mg/ml ; 0.00586 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.62
Solubility : 0.329 mg/ml ; 0.00238 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 151-10-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 151-10-0 ]

* 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 [ 151-10-0 ]

[ 151-10-0 ] Synthesis Path-Downstream   1~13

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YieldReaction ConditionsOperation in experiment
aluminium trichloride; In hexane; dichloromethane; Step 1 1,3 dimethoxybenzene (57.0 grams, 0.41 mole) and p-anisoyl chloride (69.0 grams, 0.41 mole) were added to a reaction flask containing 1000 milliliters of methylene chloride. Aluminum chloride (61.0 grams, 0.45 mole) was added slowly and the resulting mixture was stirred for 4 hours under a nitrogen atmosphere. The reaction mixture was added to a 10 weight percent aqueous hydrochloric acid solution containing ice and stirred for about thirty minutes. The organic layer was separated and the aqueous layer was back extracted with 100 milliliters of methylene chloride. The organic portions were combined and washed with water and washed again with a dilute sodium hydroxide solution. The organic layer was dried over magnesium sulfate and the residual methylene chloride was removed under vacuum. The resulting oily product (96.0 grams) solidified upon standing. The solid was crushed, added to hexane, filtered, washed with hexane, and dried. The resulting product, 2,4,4'-trimethoxy-benzophenone was not purified further but used directly in the next step.
aluminium trichloride; In dichloromethane; Step 1 1,3-Dimethoxybenzene (13.8 grams, 0.1 mole) and p-anisoyl chloride (17 grams, 0.1 mole) were dissolved in 200 milliliters of methylene chloride and stirred at room temperature. Anhydrous aluminum chloride (15 grams) was added slowly to the reaction mixture over a period of 15 minutes with stirring. After stirring an additional 15 minutes, the contents of the flask were carefully poured into 200 milliliters of a mixture of ice and dilute hydrochloric acid. The organic fraction was separated and washed with water. The solvent was removed on a rotary evaporator leaving an oily product that solidified on standing. This solid was broken-up, washed with two 50 milliliter portions of pentane, and dried, yielding 2,4,4'-trimethoxybenzophenone.
1, 3-Dimethoxybenzene (13.8 g) and p-anisoyl chloride (17 g) were dissolved in a reaction flask containing 200 mL of methylene chloride and stirred at room temperature. Anhydrous aluminum chloride (15 g) was added slowly to the reaction mixture over a period of 15 minutes with stirring. After stirring an additional 15 minutes, the contents of the flask were carefully poured into 200 mL of a mixture of ice and dilute hydrochloric acid. The organic fraction was separated and washed with water. The solvent was removed on a rotary evaporator leaving an oily product that solidified on standing. This solid was broken-up, washed with two 50 rnL portions of pentane, and dried, yielding (2,4-dimethoxy- phenyl) - (4-methoxy-phenyl)-methanone.
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  • 2,5,6-Trifluoro-2',6'-dimethoxy-biphenyl-3,4-dicarbonitrile [ No CAS ]
  • 2,5,6-Trifluoro-2',4'-dimethoxy-biphenyl-3,4-dicarbonitrile [ No CAS ]
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YieldReaction ConditionsOperation in experiment
52% EXAMPLES Production Example (A) Synthesis of Intermediate (A) [Show Image] (A-1) Synthesis of 1-bromo-2,6-dimethoxybenzene In the atmosphere of argon, 19.3g of 1,3-dimethoxybenzene and 500 mL of anhydrous diethyl ether were placed in a flask. 105 mL (1.6M) of a hexane solution of n-butyllithium was added, and the resulting reaction solution was stirred with heating for 4 hours. After cooling to room temperature while stirring, the reaction solution was cooled to -50C, followed by dropwise addition of 25g of bromine. Then, while heating the reaction solution to room temperature, stirring was conducted for 2 hours. Then, 300 mL of an aqueous 10% sodium thiosulfate solution was added, and the resulting mixture was stirred for 1 hour. The reaction solution was extracted with ether, and an aqueous phase was removed, and then, an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate and concentrated. Residues were purified by means of silica gel column chromatography. The resulting crystals were washed with hexane, whereby 17.9g (yield: 52%) of white crystals of 1-bromo-2,6-dimethoxybenzene were obtained.
52% Under an argon atmosphere 1,3-dimethoxy benzene (19.3g), was charged with anhydrous diethyl ether (500mL) to the flask, added 1.6M n-butyl lithium in hexane solution (105mL), the reaction solution was stirred for 4 hours under heating. After cooling to room temperature with continuous stirring, cooled to -50 C., was added dropwise bromine (25 g). The reaction solution was stirred for 2 hours while warming to room temperature. 10% aqueous solution of sodium thiosulfate (300mL) added, and the mixture was stirred for 1 hour. The reaction solution was extracted with ether, after removing the aqueous layer, the organic layer was washed with saturated brine. The organic layer was dried over magnesium sulfate, concentrated, and the residue was purified by silica gel chromatography. The obtained crystals were washed with hexane to obtain Intermediate 14 (17.9g). The yield was 52%.
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YieldReaction ConditionsOperation in experiment
74% With 4-chloromorpholine; ammonium peroxydisulfate; tris(bipyridine)ruthenium(II) dichloride hexahydrate; In acetonitrile; for 16.0h;Irradiation; General procedure: In a 5mL crimp cap vial 0.25mmol of the respective substrate, together with 0.3mmol (1.2equiv) of the N-chloramine or NCS, 0.3mmol (1.2equiv) (NH4)2S2O8, and 2mol% (0.005mmol) [Ru(bpy)3]Cl2×6H2O were dissolved in 2mL of MeCN/water 4:1. The reaction mixture was degassed by three cycles of freeze-pump-thaw and irradiated for 16h with blue LEDs (lambdamax=455nm). For GC analysis 500muL of the reaction mixture was added to 500muL of the standard solution (0.1M), anisole for dimethoxybenzene, toluene for anisole, mixed, filtered and submitted to GC analysis. For Tables 4 and 5: After the irradiation the internal standard (0.01mmol n-pentadecane) was added to the reaction and the reaction was immediately quenched with satd Na2CO3-solution and brine. The mixture was extracted with ethyl acetate and subjected to GC-FID analysis.
With N-chloro-succinimide; n-butyllithium; In 1,2-dimethoxyethane; (a) N-Chlorosuccimide Method To a solution of 1,3-dimethoxybenzene (13.8 g) in 1,2-dimethoxyethane (100 ml) is added 2.6M n-butyllithium (40 ml). After 40 minutes, N-chlorosuccinimide (13.5 g) is added and the reaction temperature is maintained below 55 C. by means of an ice-bath. After an additional 45 minutes, the reaction mixture is poured into water and extracted with ether. Evaporation of the organic extract affords an oil which is choromatographed on silica gel (125 g), eluding with 20% ether-hexane. Evaporation of the eluents affords an oil which crystallized on standing. Recrystallization from hexane gives 2-chloro-1,3-dimethoxybenzene, mp 62-64 C. ANALYSIS: Calculated for C8 H9 C102: 55.66%C, 5.25%H, 20.54%Cl. Found: 55.75%C, 5.20%H, 20.24%Cl.
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