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[ CAS No. 5000-65-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 5000-65-7
Chemical Structure| 5000-65-7
Chemical Structure| 5000-65-7
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Product Details of [ 5000-65-7 ]

CAS No. :5000-65-7 MDL No. :MFCD00000199
Formula : C9H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IOOHBIFQNQQUFI-UHFFFAOYSA-N
M.W : 229.07 Pubchem ID :101294
Synonyms :

Calculated chemistry of [ 5000-65-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.0
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) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 2.63
Log Po/w (WLOGP) : 2.27
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 2.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.09
Solubility : 0.187 mg/ml ; 0.000814 mol/l
Class : Soluble
Log S (Ali) : -2.83
Solubility : 0.337 mg/ml ; 0.00147 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0419 mg/ml ; 0.000183 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 5000-65-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5000-65-7 ]

* 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 [ 5000-65-7 ]
  • Downstream synthetic route of [ 5000-65-7 ]

[ 5000-65-7 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
100% With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 1 h; To a stirred clear yellow solution of l-(3-methoxyphenyl)ethanone (20 n L, 139 mmol) in tetrahydrofuran (250 mL) was added portionwise phenyltrimethylammonium tribromide (54.7 g, 145 mmol) at room temperature and stirred for lh. Then, the ammonium salts were filtered off and the filter cake was washed with ether. The filtrate was concentrated under reduced pressure and the resultant oily product was used without further purification Yielded 2-bromo-l-(3- methoxyphenyl)ethanone (32.6 g, 142 mmol, quantitative yield).
84% With hydrogen bromide; potassium iodide; sodium nitrite In water; acetonitrile at 0 - 20℃; for 10 h; General procedure: In a RBF cooled in ice bath at 0 C, HBr(12 mmol, in 2 ml of water) was taken. To this a solution of NaNO2(5 mmol, in 5ml of water) was added drop wise. The reaction was stirred for 15min maintaining the temperature at 0 °C and KI (5 mol percent) was added. After 10 min ketone(10 mmol) was added at once. After 15 min reaction temperature was brought to room temperature slowly. Reaction was monitored by TLC (ethyl acetate: pet ether, 1:9). After completion of reaction 50 ml of CHCl3 was added and organic layer separated. Aqueous layer was extracted with 25 ml of CHCl3 and combined organic layer was washed with 10percent NaHSO3 solution (2 x 20 ml) and 10percent NaHCO3 solution (2 x 20 ml).The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Pure product was obtained after column chromatography (silica gel, 60-120, eluentethyl acetate: pet ether).
84% With bromine In chloroform at 20℃; Intermediate 65. 2-bromo-1-(3-methoxyphenyl)ethanone; To a solution of 1-(3-methoxyphenyl)ethanone (5.5 ml_, 40 mmol) in chloroform (100 ml.) was added dropwise a solution of bromine (2.05 mL, 40 mmol) in chloroform (20 mL). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was diluted in methylene chloride (50 mL) and washed with water (2 x 25mL). The organic layer was dried (Na2SO4) and the solvent removed under reduced pressure. Purification by column cromatography using methylene chloride as eluent gave the title compound (8.44 g, 84percent) as oil.1H NMR (300 MHz, CDCI3): 3.9 (s, 3H); 4.5 (s, 2H); 7.14-7.18 (dd, J=I Λ, 3.2 Hz, 1H); 7.43 (t, J=8.0 Hz, 1 H); 7.51-7.58 (m, 2H).
80.9%
Stage #1: With N-Bromosuccinimide In ethyl acetate at 20℃; for 3 h;
Stage #2: With sodium hydroxide In ethyl acetate
In the reactor,260 g (1.5 mol) of NBS (N-bromosuccinimide) were added,230 g of ethyl acetate and 150 g of 3-methoxyacetophenone prepared in S4 and thoroughly mixed,Room temperature reaction 3h,Hydrogen bromide generated by the absorption of sodium hydroxide solution,Completed the reaction,Ethyl acetate was distilled off,Then the reaction solution was added to water,A solid precipitation,filter,Dried in crude,Recrystallization from ethyl acetate gave 185.3 g of 2-bromo-3'-methoxyacetophenone as a pale yellow powder,The yield was 80.9percent

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Reference: [1] Patent: CN106242957, 2016, A,
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Reference: [1] Patent: CN106242957, 2016, A,
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Reference: [1] Patent: CN106242957, 2016, A,
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 11, p. 2575 - 2582
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 11, p. 2575 - 2582
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