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[ CAS No. 1428761-26-5 ] {[proInfo.proName]}

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Chemical Structure| 1428761-26-5
Chemical Structure| 1428761-26-5
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Product Details of [ 1428761-26-5 ]

CAS No. :1428761-26-5 MDL No. :N/A
Formula : C10H10BrClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BVGLGRSNXOOBSX-UHFFFAOYSA-N
M.W : 277.54 Pubchem ID :53703085
Synonyms :

Calculated chemistry of [ 1428761-26-5 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.98
TPSA : 26.3 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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 3.39
Log Po/w (WLOGP) : 3.13
Log Po/w (MLOGP) : 3.53
Log Po/w (SILICOS-IT) : 3.85
Consensus Log Po/w : 3.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.82
Solubility : 0.0424 mg/ml ; 0.000153 mol/l
Class : Soluble
Log S (Ali) : -3.62
Solubility : 0.0664 mg/ml ; 0.000239 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.73
Solubility : 0.00514 mg/ml ; 0.0000185 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.09

Safety of [ 1428761-26-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1428761-26-5 ]

* 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 [ 1428761-26-5 ]

[ 1428761-26-5 ] Synthesis Path-Downstream   1~12

  • 1
  • 1-bromo-2-chloro-5-methyl-4-nitrobenzene [ No CAS ]
  • [ 1428761-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16 h / 90 °C 2: sodium periodate; ruthenium(III) chloride monohydrate; tetra-(n-butyl)ammonium iodide / water; ethyl acetate / 0 - 20 °C 3: thionyl chloride / 4 h / 100 °C 4: sodium tetrahydroborate; nickel (II) chloride hexahydrate / methanol / 40 h / 0 - 20 °C 5: tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide / acetonitrile / 20 °C
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16 h / 90 °C 2.1: ruthenium(III) chloride trihydrate; tetra-(n-butyl)ammonium iodide / ethyl acetate / 0 °C 2.2: 2 h / 20 °C 3.1: thionyl chloride / 4.25 h / 100 °C 4.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / water; methanol / 0.67 h / 0 - 20 °C 5.1: copper(ll) bromide; tert.-butylnitrite; toluene-4-sulfonic acid; tetrabutylammomium bromide / acetonitrile / 4 h / 20 °C
  • 2
  • [ 57310-39-1 ]
  • [ 1428761-26-5 ]
  • 3
  • [ 1428761-23-2 ]
  • [ 1428761-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium periodate; ruthenium(III) chloride monohydrate; tetra-(n-butyl)ammonium iodide / water; ethyl acetate / 0 - 20 °C 2: thionyl chloride / 4 h / 100 °C 3: sodium tetrahydroborate; nickel (II) chloride hexahydrate / methanol / 40 h / 0 - 20 °C 4: tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide / acetonitrile / 20 °C
Multi-step reaction with 4 steps 1.1: ruthenium(III) chloride trihydrate; tetra-(n-butyl)ammonium iodide / ethyl acetate / 0 °C 1.2: 2 h / 20 °C 2.1: thionyl chloride / 4.25 h / 100 °C 3.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / water; methanol / 0.67 h / 0 - 20 °C 4.1: copper(ll) bromide; tert.-butylnitrite; toluene-4-sulfonic acid; tetrabutylammomium bromide / acetonitrile / 4 h / 20 °C
  • 4
  • [ 1428761-24-3 ]
  • [ 1428761-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 4 h / 100 °C 2: sodium tetrahydroborate; nickel (II) chloride hexahydrate / methanol / 40 h / 0 - 20 °C 3: tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide / acetonitrile / 20 °C
Multi-step reaction with 3 steps 1: thionyl chloride / 4.25 h / 100 °C 2: nickel(II) chloride hexahydrate; sodium tetrahydroborate / water; methanol / 0.67 h / 0 - 20 °C 3: copper(ll) bromide; tert.-butylnitrite; toluene-4-sulfonic acid; tetrabutylammomium bromide / acetonitrile / 4 h / 20 °C
  • 5
  • [ 1428761-25-4 ]
  • [ 1428761-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; nickel (II) chloride hexahydrate / methanol / 40 h / 0 - 20 °C 2: tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide / acetonitrile / 20 °C
Multi-step reaction with 2 steps 1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / water; methanol / 0.67 h / 0 - 20 °C 2: copper(ll) bromide; tert.-butylnitrite; toluene-4-sulfonic acid; tetrabutylammomium bromide / acetonitrile / 4 h / 20 °C
  • 6
  • [ 1428761-26-5 ]
  • [ 1432909-83-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene; tetrahydrofuran; water / 18 h / Reflux; Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene; tetrahydrofuran; water / 18 h / Inert atmosphere; Reflux
  • 7
  • [ 1428761-26-5 ]
  • [ 1432909-88-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: zinc; tris-(dibenzylideneacetone)dipalladium(0); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 120 °C / Inert atmosphere 2: hydroxylamine hydrochloride; sodium hydrogencarbonate / methanol / 4 h / 70 °C 3: 16 h / Reflux
  • 8
  • [ 1428761-26-5 ]
  • [ 1432909-86-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc; tris-(dibenzylideneacetone)dipalladium(0); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 120 °C / Inert atmosphere 2: hydroxylamine hydrochloride; sodium hydrogencarbonate / methanol / 4 h / 70 °C
  • 9
  • [ 1428761-26-5 ]
  • [ 73183-34-3 ]
  • [ 1432909-81-3 ]
YieldReaction ConditionsOperation in experiment
1.2 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In tetrahydrofuran; water; toluene for 18h; Reflux; Inert atmosphere; 7 Step 7: Synthesis of methyl 2-(2-chloro-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (14A) Step 7: Synthesis of methyl 2-(2-chloro-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (14A) A mixture of methyl 2-(4-bromo-2-chloro-5-methylphenyl)acetate (2.7 g, 9.78 mmol, 1 eq), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (3.23 g, 12.72 mmol, 1.3 eq), KOAc (1.92 g, 19.56 mmol, 2 eq) and Pd(dppf)C12 (500 mg) was refluxed in 30 mL of toluene/THF/H2O (0.5 ml/0.5 ml/0.25 ml) under N2 for 18 h. This mixture was filtered and the filtrate was diluted with water (50 mL) and extracted with EtOAc (50 mL*3). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give 1.2 g of 14A. 1H NMR (400 MHz, DMSO-d6) d ppm 7.74 (s, 1H), 7.06 (s, 1H), 3.73 (s, 2H), 3.69 (s, 3H), 2.47 (s, 3H), 1.33-1.32 (dd, 12H).
  • 10
  • [ 1428761-26-5 ]
  • [ 1692-25-7 ]
  • [ 1428761-27-6 ]
YieldReaction ConditionsOperation in experiment
76% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In tetrahydrofuran; water; toluene at 90℃; for 4h; Inert atmosphere; 285.7 Step 7: Synthesis of methyl 2-(2-chloro-5-methyl-4-(pyridin-3-yl) phenyl) acetate (172) A mixture of methyl 2-(4-bromo-2-chloro-5-methylphenyl) acetate (280 mg, 1 mmol, 1.0 eq), pyridin-3-ylboronic acid (140 mg, 1.2 eq), K2C03 (276 mg, 2.0eq), and Pd(dppf)Cl2 in toluene/THF/H20 (5 mL, 2:2: 1 ) was stirred at 90 °C for 4h under N2. Water (30 mL) was added to the reaction mixture. The mixture was extracted with ethyl acetate (3x10ml), dried over Na2S04, filtered and concentrated. The crude material was purifed by silical gel column chromatography (PE: ethyl acetate=10: 1) to afford 172 (210 mg, 76%) as a white solid. LCMS: m/z 276 (M+l)+.
  • 11
  • [ 192650-79-6 ]
  • [ 1428761-26-5 ]
YieldReaction ConditionsOperation in experiment
With tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide In acetonitrile at 20℃; 285.6 Step 6: Synthesis of methyl 2-(4-bromo-2-chloro-5-methylphenyl) acetate (171) To a solution of methyl 2-(4-amino-2-chloro-5-methylphenyl)acetate (2.0 g, 4.68 mmol, 1.0 eq), t-BuONO (580 mg, 1.2 eq), p-TsOH (972 mg, 1.2 eq), TBAB (3.0 g, 2.0 eq) in CH3CN (50 mL), was added CuBr (14.4 mg, lmol%). The reaction was stirred at room temperature for 3-4h, then concentrated. The mixture was dissolved in DCM (30 mL), washed with saturated aq NaHC03 (8x20 mL), H20 (2x10 mL), dried over Na2S04, filtered and concentrated to afford 171 (2.2 g), which was used the next step directly without further purification. Ή NMR (400 MHz, CDCb) ppm: 7.54 (s, 1 H), 7.13 (s, 1 H), 3.72 (s, 3H), 3.67 (s, 2H), 2.38 (s, 3H).
1 g With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 4h; 6 Step 6: Synthesis of methyl 2-(4-bromo-2-chloro-5-methylphenyl)acetate (13A) Step 6: Synthesis of methyl 2-(4-bromo-2-chloro-5-methylphenyl)acetate (13A) CuBr2 (10 mg) was added to a solution of methyl 2-(4-amino-2-chloro-5-methylphenyl)acetate (1.0 g, 4.68 mmol, 1.0 eq), t-BuONO (580 mg, 1.2 eq), p-TsOH (972 mg, 1.2 eq), TBAB (3.0 g, 2.0 eq) in CH3CN (50 ml) and stirred at room temperature for 4 h. The reaction mixture was concentrated, and then dissolved in dichloromethane (30 ml), washed with saturated aq NaHCO3 (20 ml*8), H2O (10 ml*2), dried over anhydrous Na2SO4, filtered and concentrated to afford 1 g of 13A which was used directly in the next step without further purification.
  • 12
  • [ 557-21-1 ]
  • [ 1428761-26-5 ]
  • [ 1432909-85-7 ]
YieldReaction ConditionsOperation in experiment
12% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium(0); zinc In N,N-dimethyl-formamide at 120℃; for 1.5h; Inert atmosphere; 1 Step 1: Step 1: Synthesis of methyl 2-(2-chloro-4-cyano-5-methylphenyl)acetate (17A) A mixture of methyl 2-(4-bromo-2-chloro-5-methylphenyl)acetate 16A (4 g, 14.49 mmol, 1 eq), Zn(CN)2 (1.7 g, 14.49 mmol, 1 eq) and Zn (94.2 mg, 1.45 mmol, 0.1 eq) in anhydrous DMF (40 mL) was added Pd(dppf)Cl2 (500 mg) and Pd2(dba)3 (500 mg) under N2. The mixture was stirred at 120° C. for 1.5 h, then cooled to room temperature, diluted with water (50 mL) and extracted with EtOAc (3*50 mL). The organic layers were combined and washed with water (3*50 mL), brine (2*50 mL), dried over anhydrous Na2SO4, filtered and concentrated to give a crude product, which was purified by column chromatography with silica gel (PE/ethyl acetate=10:1 to 3:1) to afford 17A (0.4 g, 12%).
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