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[ CAS No. 16740-73-1 ] {[proInfo.proName]}

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Chemical Structure| 16740-73-1
Chemical Structure| 16740-73-1
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Product Details of [ 16740-73-1 ]

CAS No. :16740-73-1 MDL No. :MFCD03789141
Formula : C9H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GLKBPFOSTPLEKE-UHFFFAOYSA-N
M.W : 229.07 Pubchem ID :2757029
Synonyms :

Calculated chemistry of [ 16740-73-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.83
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) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 2.51
Log Po/w (WLOGP) : 2.66
Log Po/w (MLOGP) : 2.16
Log Po/w (SILICOS-IT) : 2.84
Consensus Log Po/w : 2.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.08
Solubility : 0.191 mg/ml ; 0.000833 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.449 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.72
Solubility : 0.0436 mg/ml ; 0.000191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 16740-73-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16740-73-1 ]

* 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.

  • Upstream synthesis route of [ 16740-73-1 ]
  • Downstream synthetic route of [ 16740-73-1 ]

[ 16740-73-1 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 579-74-8 ]
  • [ 16740-73-1 ]
YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide; iodine In acetonitrile for 12 h; Darkness General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 molpercent, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)
95% With hydrogenchloride; N-Bromosuccinimide In water; acetone at 20℃; for 3 h; Compound 41-2 (0492) To a solution of 41-1 (2.0 g, 13.32 mmol) in acetone (25 mL) was added NBS (2.37 g, 13.32 mmol) and 1M HCl aq. (0.13 mL, 0.13 mmol). The reaction mixture was stirred at room temperature for 3 h, and then concentrated to dryness under reduced pressure. The residue was dissolved with PE (40 mL) the resultant precipitate was filtered and dried in vacuum to afford 41-2 as a white solid (2.90 g, yield: 95percent).
Reference: [1] Tetrahedron, 2017, vol. 73, # 50, p. 7105 - 7114
[2] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4707 - 4710
[3] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 312-313
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 1423 - 1428
[5] Synthesis (Germany), 2013, vol. 45, # 11, p. 1497 - 1504
  • 2
  • [ 1450-75-5 ]
  • [ 74-88-4 ]
  • [ 16740-73-1 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate In acetone 1-(5-Bromo-2-methoxy-phenyl)-ethanone
A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (10 g, 47 mmol), methyl iodide (3.5 mL, 56 mmol), and potassium carbonate (10 g, 73 mmol) in acetone (80 mL) was heated at reflux for 4 h.
The reaction mixture was cooled to room temperature and the resulting white solid filtered and washed thoroughly with ethyl acetate.
The filtrate was washed with water, brine, dried over MgSO4 and filtered.
The filtrate was concentrated in vacuo to provide the title compound (10 g, 94percent) as a white solid.
91%
Stage #1: With potassium carbonate In [(2)H6]acetone at 20℃; for 1 h;
Stage #2: at 20℃; for 20 h;
Potassium carbonate (9.6 g) was added to a solution of 1-(5-bromo-2-hydroxyphenyl)ethanone (4.98 g) in acetone (50 mL) and the suspension was stirred at rt for 1 h.
Methyl iodide (1.89 mL) was added and the reaction mixture was stirred at rt for 20 h at which time it was filtered and the volatiles were removed under reduced pressure.
The residue was diluted in Et2O and was washed with water.
The organic layer was dried and the solvent was removed under reduced pressure to yield the desired product (91percent yield).
LC-MS (Method 1): m/z [M+H]+=229.1 (MW calc.=229.07); Rt=3.30 min.
91%
Stage #1: With potassium carbonate In acetone at 20℃; for 1 h;
Stage #2: at 20℃; for 20 h;
Intermediate 7a) Potassium carbonate (9.6 g) was added to a solution of 1 -(5-bromo-2-hydroxyphenyl)ethanone (4.98 g) in acetone (50 mL) and the suspension was stirred at rt for 1 h. Methyl iodide (1.89 mL) was added and the reaction mixture was stirred at rt for 20 h at which time it was filtered and the volatiles were removed under reduced pressure. The residue was diluted in Et20 and was washed with water. The organic layer was dried and the solvent was removed under reduced pressure to yield the desired product (91 percent yield). LC-MS (Method 1): m/z [M+H]+ = 229.1 (MW calc. = 229.07); R, = 3.30 min.
89% With potassium carbonate In N,N-dimethyl-formamide at 20℃; A mixture of 5-Bromo-2-hydroxyacetophenone 2a (10g, 46.5mmol, 1 eq), potassium carbonate (9.62g, 69.75mmol, 1.5 eq) and iodomethane (5.8mL, 93mmol, 2 eq) in DMF (120mL) were stirred overnight in a sealed round bottom flask at room temperature. DMF was removed under reduced pression and the residue was partitioned between water and EtOAc. The combined EtOAc extracts were washed with brine, 0.5M NaOH and then three times with water. The organic layer was dried over MgSO4 and the solvent evaporated. The product was obtained as an off-white solid (9.5g, 89percent). m.p. 31–32°C. SM (ESI): m/z 251–253 [M+Na]+. 1H NMR (δ ppm): 2.54 (s, 3H, COCH3), 3.90 (s, 3H, OCH3), 7.18 (d, Jortho=8.9Hz, 1H, CHar), 7.66 (d, Jmeta=2.6Hz, 1H, CHar), 7.72 (dd, Jortho=8.9Hz, Jmeta=2.6Hz, 1H, CHar).
75% With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12 h; Inert atmosphere To a stirred solution of 1 -(5-bromo-2-hydroxyphenyl)ethan- 1-one 1 (10 g, 46.51 mmol) in DMF (100 mL) were added K2C03 (9.63 g, 69.77 mmol) and Mel (5.8 mL, 93.02 mmol) at 0°C under Ar. The mixture was stirred at RT for 12 h then quenched with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine (80 mL), dried over Na2 SO4, filtered and concentrated under reduced pressure to afford compound 2 (8.8 g, 75percent) as pale yellow liquid. ‘H NIVIR (500MHz, DMSO-d6): 7.70 (dd, J 9.0, 2.6 Hz, 1H), 7.64 (d, J= 2.6 Hz, 1H), 7.16 (d, J= 9.0 Hz, 1H), 3.88 (s, 3H), 2.52 (s, 3H); LC-MS (ESI):m/z 228.8 (M + Hf).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 15, p. 2561 - 2563
[2] Tetrahedron, 2001, vol. 57, # 24, p. 5027 - 5038
[3] Chemistry - A European Journal, 2016, vol. 22, # 30, p. 10415 - 10419
[4] Patent: US2003/187007, 2003, A1,
[5] Patent: US2014/194443, 2014, A1, . Location in patent: Paragraph 0427-0429
[6] Patent: WO2014/108337, 2014, A1, . Location in patent: Page/Page column 56; 57
[7] European Journal of Medicinal Chemistry, 2018, vol. 144, p. 774 - 796
[8] Journal of the Chemical Society. Perkin Transactions 1, 2002, # 8, p. 1115 - 1123
[9] Patent: WO2017/15221, 2017, A1, . Location in patent: Paragraph 00255
[10] Organic and Biomolecular Chemistry, 2005, vol. 3, # 24, p. 4432 - 4443
[11] Advanced Synthesis and Catalysis, 2018, vol. 360, # 8, p. 1634 - 1638
  • 3
  • [ 104-92-7 ]
  • [ 75-36-5 ]
  • [ 16740-73-1 ]
Reference: [1] Patent: US6037488, 2000, A,
  • 4
  • [ 104-92-7 ]
  • [ 7664-93-9 ]
  • [ 874-60-2 ]
  • [ 16740-73-1 ]
Reference: [1] Patent: US6037488, 2000, A,
  • 5
  • [ 14804-32-1 ]
  • [ 16740-73-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 4, p. 784 - 787
  • 6
  • [ 1761-61-1 ]
  • [ 16740-73-1 ]
Reference: [1] Drug Metabolism and Disposition, 2012, vol. 40, # 10, p. 2002 - 2008,7
  • 7
  • [ 25016-01-7 ]
  • [ 16740-73-1 ]
Reference: [1] Drug Metabolism and Disposition, 2012, vol. 40, # 10, p. 2002 - 2008,7
  • 8
  • [ 16602-17-8 ]
  • [ 16740-73-1 ]
Reference: [1] Drug Metabolism and Disposition, 2012, vol. 40, # 10, p. 2002 - 2008,7
  • 9
  • [ 1927-95-3 ]
  • [ 16740-73-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 15, p. 2561 - 2563
  • 10
  • [ 104-92-7 ]
  • [ 108-24-7 ]
  • [ 16740-73-1 ]
  • [ 100-06-1 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1946, vol. 223, p. 159
  • 11
  • [ 7446-70-0 ]
  • [ 104-92-7 ]
  • [ 108-24-7 ]
  • [ 16740-73-1 ]
  • [ 100-06-1 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1946, vol. 223, p. 159
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