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[ CAS No. 93-04-9 ] {[proInfo.proName]}

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Chemical Structure| 93-04-9
Chemical Structure| 93-04-9
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Product Details of [ 93-04-9 ]

CAS No. :93-04-9 MDL No. :MFCD00004061
Formula : C11H10O Boiling Point : -
Linear Structure Formula :- InChI Key :LUZDYPLAQQGJEA-UHFFFAOYSA-N
M.W : 158.20 Pubchem ID :7119
Synonyms :

Calculated chemistry of [ 93-04-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.44
TPSA : 9.23 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) : -4.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.29
Log Po/w (XLOGP3) : 3.47
Log Po/w (WLOGP) : 2.85
Log Po/w (MLOGP) : 2.83
Log Po/w (SILICOS-IT) : 3.0
Consensus Log Po/w : 2.89

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.56
Solubility : 0.0438 mg/ml ; 0.000277 mol/l
Class : Soluble
Log S (Ali) : -3.35
Solubility : 0.0713 mg/ml ; 0.000451 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.19
Solubility : 0.0103 mg/ml ; 0.000065 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 93-04-9 ]

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 [ 93-04-9 ]

* 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.

  • Upstream synthesis route of [ 93-04-9 ]
  • Downstream synthetic route of [ 93-04-9 ]

[ 93-04-9 ] Synthesis Path-Upstream   1~18

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Reference: [1] Patent: US2018/208716, 2018, A1, . Location in patent: Paragraph 0023; 0089-0095
  • 2
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YieldReaction ConditionsOperation in experiment
98% With tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide In acetonitrile at 20℃; Irradiation General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar were added phenols or alkenes (0.1 mmol), CBr4 (33 mg, 0.1 mmol), dry CH3CN (1 mL) and Ru(bpy)3Cl2 (3.8 mg, 0.005 mmol). The mixture was irradiated with blue LEDs (1 W) at room temperature open to air until the starting material disappeared completely (monitored by TLC). After the reaction was completed, the solvent was concentrated in vacuo. The residue was purified by flash column chromatography to give the final product.
90% With N-Bromosuccinimide In neat (no solvent) at 20℃; for 0.75 h; Milling; Green chemistry General procedure: 1-Methoxy-3,5-dimethylbenzene(100mg, 0.73 mmol), N-Bromosuccinimide (NBS,260 mg,1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reaction was monitored by TLC/1H NMR.[1]After completion, the reaction mixture was transferred into 30 mL ethyl acetate and cooled at 0 °C. The product was isolated as filtrate upon paper filtration and waste succinimide as precipitate. The resulting filtrate were concentrated in vacuo to isolate 250 mg (yield: 85percent) of 2b as colourless powder. To test the efficiency in large scale, the reaction was also performed for the mono-bromination of 1-methoxy-3,5-dimethylbenzene in 1.3 g scale for 1 h and the product was isolated in 87percent yield.[1] The milling apparatus was stopped and small portion of the sample was collected from the reaction jar to study either TLC/ proton NMR. Following, the reaction was started again andthis operation time was excluded for reporting the reaction timing.
90% With N-Bromosuccinimide In neat (no solvent) at 20℃; for 0.75 h; Milling; Green chemistry General procedure: 1-Methoxy-3,5-dimethylbenzene (100mg, 0.73 mmol), N-Bromosuccinimide (NBS,260 mg,1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reactionwas monitored by TLC/1H NMR.[1]After completion, the reaction mixture was transferred into 30 mL ethyl acetateand cooled at 0 °C. The product was isolated as filtrate upon paper filtrationand waste succinimide as precipitate. The resulting filtrate were concentrated in vacuoto isolate 250 mg (yield: 85percent) of 2bas colourless powder. To test the efficiency in largescale, the reaction was also performed for the mono-bromination of1-methoxy-3,5-dimethylbenzene in 1.3 g scale for 1 h and the product wasisolated in 87percent yield.[1] Themilling apparatus was stopped and small portion of the sample was collectedfrom the reaction jar to study either TLC/ proton NMR. Following, the reaction was started again andthis operation time was excluded for reporting the reaction timing.
88 %Chromat. With carbon dioxide; oxygen; lithium bromide; copper(ll) bromide In water at 100℃; for 10 h; Autoclave; Green chemistry General procedure: A mixture of substrate (1 mmol), CuBr2 (22.4 mg, 10 molpercent), LiBr (130.3 mg, 1.5 equiv.), and 0.05 mL of water was placed in a 50 mL stainless steel autoclave equipped with an inner glass tube in room temperature. CO2 (4 MPa) and O2 (1 MPa) were subsequently introduced into the autoclave and the system was heated under the predetermined reaction temperature for 15 min to reach the equilibration. Then the final pressure was adjusted to the desired pressure by introducing the appropriate amount of CO2. The mixture was stirred continuously for the desired reaction time. After cooling, products were diluted with acetone and analyzed by gas chromatograph (Shimadzu GC-2014) equipped with a capillary column (RTX-17 30 m × 25 μm and RTX-wax 30 m × 25 μm) using a flame ionization detector by comparing the retention times of authentic samples. The residue was purified by column chromatography on silica gel (200–300 mesh, eluting with petroleum ether/ethyl acetate from petroleum ether to 50:1) to afford the desired product. The isolated products were further identified with NMR spectra (Bruker 400 MHz) and GC–MS or GCD, which are consistent with those reported in the literature.

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[3] Journal of Organic Chemistry, 1997, vol. 62, # 13, p. 4321 - 4326
[4] Synthetic Communications, 2002, vol. 32, # 15, p. 2313 - 2318
[5] Journal of Chemical Research - Part S, 2003, # 9, p. 597 - 598
[6] Organic Letters, 2017, vol. 19, # 16, p. 4243 - 4246
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[8] Tetrahedron Letters, 2008, vol. 49, # 24, p. 3844 - 3847
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[10] Green Chemistry, 2018, vol. 20, # 19, p. 4448 - 4452
[11] Synthetic Communications, 2004, vol. 34, # 12, p. 2143 - 2152
[12] Angewandte Chemie - International Edition, 2018, vol. 57, # 39, p. 12869 - 12873[13] Angew. Chem., 2018, vol. 130, p. 13051 - 13055,5
[14] Advanced Synthesis and Catalysis, 2006, vol. 348, # 7-8, p. 862 - 866
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[20] Synthetic Communications, 2005, vol. 35, # 14, p. 1947 - 1952
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[30] Advanced Synthesis and Catalysis, 2011, vol. 353, # 17, p. 3187 - 3195
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[33] Tetrahedron Letters, 2015, vol. 55, # 13, p. 2154 - 2156
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[49] Journal of Organic Chemistry, 1948, vol. 13, p. 484,485
[50] Monatshefte fuer Chemie, 1936, vol. 67, p. 332,339[51] Monatshefte fuer Chemie, 1937, vol. 70, p. 251,255
[52] Annales de Chimie (Cachan, France), 1946, vol. <12> 1, p. 395,403, 433
[53] Justus Liebigs Annalen der Chemie, 1944, vol. 556, p. 1,7
[54] Zhurnal Obshchei Khimii, 1952, vol. 22, p. 1594,1597; engl. Ausg. S. 1635, 1637
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[62] Patent: WO2007/27917, 2007, A2, . Location in patent: Page/Page column 23-24
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[64] Synthesis (Germany), 2013, vol. 45, # 11, p. 1497 - 1504
[65] Catalysis Today, 2012, vol. 194, # 1, p. 38 - 43
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Reference: [1] International Journal of Chemical Kinetics, 2014, vol. 46, # 1, p. 10 - 23
  • 4
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Reference: [1] Anales de la Asociacion Quimica Argentina (1921-2001), 1950, vol. 38, p. 188,191
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  • [ 7726-95-6 ]
  • [ 64-19-7 ]
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Reference: [1] Journal of the American Chemical Society, 1930, vol. 52, p. 4087,4090
[2] Bulletin de la Societe Chimique de France, 1942, vol. <5> 9, p. 57
[3] Journal of Organic Chemistry, 1948, vol. 13, p. 484,485
[4] Journal of the Chemical Society, 1941, p. 687
[5] Monatshefte fuer Chemie, 1936, vol. 67, p. 332,339[6] Monatshefte fuer Chemie, 1937, vol. 70, p. 251,255
[7] Annales de Chimie (Cachan, France), 1946, vol. <12> 1, p. 395,403, 433
  • 6
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Reference: [1] Anales de la Asociacion Quimica Argentina (1921-2001), 1950, vol. 38, p. 188,191
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  • [ 7789-69-7 ]
  • [ 3401-47-6 ]
Reference: [1] Chemische Berichte, 1906, vol. 39, p. 4105[2] Chemische Berichte, 1907, vol. 40, p. 749
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  • [ 128-08-5 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1944, vol. 556, p. 1,7
  • 9
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  • [ 79-05-0 ]
  • [ 2700-47-2 ]
YieldReaction ConditionsOperation in experiment
85% at 5 - 19℃; for 32.3333 h; In the is provided with an agitator, reflux condenser, thermometer, dropping funnel in the reaction container, adding triethylamine to 310 ml, stannous chloride 0.65mol, control the stirring speed 190rpm, reducing the temperature of the solution to 5 °C, β-naphthyl methyl ether is slowly added (2) 0.65mol, adds by drops third amide (3) 0.47mol, dropping time control, in 80 min, maintaining the temperature of the solution reaction 9h, raising the temperature of the solution to 19 °C, standing 22h, the reactants are poured into the 1.8L the mass fraction of 25percent sodium bisulfite solution, control the temperature of the solution in the 5 °C, steam distillation, until completely distilled until the triethylamine, control the stirring speed 130rpm, let solution of natural cooling, solidifying oily substance, filtering, potassium nitrate solution, anhydrous calcium sulfate dehydration, in the mass fraction is 92percent recrystallized in cyclohexane solution, to get the yellow solid 6-methoxy-2-c acyl-naphthaline 85.49g, yield 85percent.
Reference: [1] Patent: CN105439833, 2016, A, . Location in patent: Paragraph 0015; 0016
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[6] Proceedings - Indian Academy of Sciences, Section A, 1946, vol. <A> 24, p. 382,385
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[8] Patent: US4670603, 1987, A,
[9] Patent: EP176142, 1991, B1,
[10] Pr.roy.Soc.<B>, 1942, vol. 130, p. 435,444
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[2] Synthetic Communications, 1990, vol. 20, # 3, p. 383 - 392
[3] Synthetic Communications, 1990, vol. 20, # 3, p. 383 - 392
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 781,785
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 781,785
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  • [ 1888-41-1 ]
  • [ 67247-13-6 ]
Reference: [1] Journal of Physical Organic Chemistry, 2013, vol. 26, # 1, p. 23 - 29
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  • [ 1999-64-0 ]
Reference: [1] Proceedings - Indian Academy of Sciences, Section A, 1946, vol. <A> 24, p. 382,385
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  • [ 71-36-3 ]
  • [ 10484-56-7 ]
YieldReaction ConditionsOperation in experiment
98% With bismuth(lll) trifluoromethanesulfonate In water; 1,2-dichloro-ethane at 110℃; for 24 h; Schlenk technique; Inert atmosphere General procedure: A flame dried Schlenk flask was charged with Bi(OTf)3 (13.1 mg,0.020 mmol), alkyl aryl ethers (0.40 mmol), alcohols or thiols (1.2 mmol) andCH2ClCH2Cl (0.20 mL), and then the resulting mixture was stirred at 110 °C (or 130 °C forthe synthesis of 1m) for 24 h. The solvent was removed under the reduced pressure, andthe residue was subjected to flash column chromatography on silica gel with hexane /AcOEt as eluents to afford the corresponding aryl ethers or aryl thioethers
Reference: [1] Chemistry Letters, 2018, vol. 47, # 7, p. 927 - 930
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  • [ 104116-17-8 ]
Reference: [1] Organic Process Research and Development, 2003, vol. 7, # 3, p. 379 - 384
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  • [ 64-17-5 ]
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  • [ 38077-95-1 ]
  • [ 6836-21-1 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 17, p. 7760 - 7770
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