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[ CAS No. 1516-96-7 ] {[proInfo.proName]}

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Chemical Structure| 1516-96-7
Chemical Structure| 1516-96-7
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Product Details of [ 1516-96-7 ]

CAS No. :1516-96-7 MDL No. :MFCD12024327
Formula : C15H23BrO Boiling Point : -
Linear Structure Formula :- InChI Key :KKHJQLVAMOKQHO-UHFFFAOYSA-N
M.W : 299.25 Pubchem ID :13691541
Synonyms :

Calculated chemistry of [ 1516-96-7 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.6
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 79.17
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.69
Log Po/w (XLOGP3) : 5.93
Log Po/w (WLOGP) : 5.05
Log Po/w (MLOGP) : 4.76
Log Po/w (SILICOS-IT) : 5.05
Consensus Log Po/w : 4.9

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.49
Solubility : 0.000959 mg/ml ; 0.0000032 mol/l
Class : Moderately soluble
Log S (Ali) : -5.9
Solubility : 0.000378 mg/ml ; 0.00000126 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.79
Solubility : 0.000489 mg/ml ; 0.00000163 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 1516-96-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1516-96-7 ]

* 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 [ 1516-96-7 ]
  • Downstream synthetic route of [ 1516-96-7 ]

[ 1516-96-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1139-52-2 ]
  • [ 77-78-1 ]
  • [ 1516-96-7 ]
YieldReaction ConditionsOperation in experiment
95.2% With potassium carbonate In acetone at 22℃; for 13 h; Heating / reflux Reference Example 6
4-bromo-2,6-di-tert-butylanisole
Under an argon atmosphere, to a solution of 4-bromo-2,6-di-tert-butylphenol (50 g, 0.175 MoL) and potassium carbonate (96.7 g, 4.0 equivalents) in acetone (750 ML) was added dimethyl sulfate (38.6 g, 1.75 equivalents) at 22°C, and the mixture was stirred under reflux for 13 hrs..
Insoluble materials were filtered off and the solvent was evaporated under reduced pressure..
ethyl acetate (150 ML) and water (100 ML) were added, the mixture was partitioned, and the organic layer was washed successively with water (100 ML), 5percent aqueous NaHCO3 solution (100 ML) and 5percent aqueous NaCl solution (100 ML)..
The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure to give the title compound (56.1 g, brown oil)..
yield 95.2percent1H-NMR (300MHz, CDCl3, TMS) δ: 1.41 (s, 18H), 3.68 (s, 3H), 7.33 (s, 2H).
95.2% With potassium carbonate In acetone at 22℃; for 13 h; Heating / reflux Reference Example 2
4-Bromo-2,6-di-tert-butylanisole
Under argon atmosphere, to a solution of 4-bromo-2,6-di-tert-butylphenol (50 g, 0.175 mol) and potassium carbonate (96.7 g, 4.0 equivalents) in acetone (750 mL) was added dimethyl sulfate (38.6 g, 1.75 equivalents) at 22°C.
The mixture was stirred under reflux for 13 hours.
Insoluble substances were filtered off and the solvent was distilled off under reduced pressure.
By adding ethyl acetate (150 mL) and water (100 mL) to the residue, the reaction mixture was allowed to separate into layers.
An organic layer was washed successively with water (100 mL), a 5percent NaHCO3 aqueous solution (100 mL) and a 5percent NaCl aqueous solution (100 mL), dried over anhydrous magnesium sulfate and then naturally filtered.
The filtrate was concentrated under reduced pressure to obtain the title compound (56.1 g, brown oil).
Yield 95.2percent.
1H-NMR (300 MHz, CDCl3, TMS) δ: 1.41 (s, 18H), 3.68 (s, 3H), 7.33 (s, 2H).
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 51, p. 16486 - 16487
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 33, p. 9738 - 9742[3] Angew. Chem., 2016, vol. 128, # 33, p. 9890 - 9894,5
[4] Patent: EP1452537, 2004, A1, . Location in patent: Page 27
[5] Patent: EP1568701, 2005, A1, . Location in patent: Page/Page column 13
[6] Synthesis, 2010, # 13, p. 2124 - 2128
  • 2
  • [ 1139-52-2 ]
  • [ 74-88-4 ]
  • [ 1516-96-7 ]
Reference: [1] Organic Letters, 2008, vol. 10, # 23, p. 5429 - 5432
[2] Chemistry - A European Journal, 2014, vol. 20, # 14, p. 4098 - 4104
[3] Chemistry - A European Journal, 2018, vol. 24, # 18, p. 4528 - 4531
[4] Journal of Organic Chemistry, 2008, vol. 73, # 3, p. 1143 - 1146
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1539 - 1543[6] Angew. Chem., 2017, vol. 129, # 6, p. 1561 - 1565,5
[7] Canadian Journal of Chemistry, 1966, vol. 44, p. 2855 - 2866
[8] Patent: US2011/166372, 2011, A1, . Location in patent: Page/Page column 24
  • 3
  • [ 1516-95-6 ]
  • [ 1516-96-7 ]
Reference: [1] European Journal of Organic Chemistry, 2008, # 10, p. 1767 - 1776
[2] Patent: US2009/30012, 2009, A1, . Location in patent: Page/Page column 15
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