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[ CAS No. 21849-89-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 21849-89-8
Chemical Structure| 21849-89-8
Chemical Structure| 21849-89-8
Structure of 21849-89-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 21849-89-8 ]

CAS No. :21849-89-8 MDL No. :MFCD11933563
Formula : C12H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :ZGOWIHIGUHWAMQ-UHFFFAOYSA-N
M.W :249.10 Pubchem ID :18795255
Synonyms :

Calculated chemistry of [ 21849-89-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.6
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 3.78
Log Po/w (WLOGP) : 3.82
Log Po/w (MLOGP) : 3.75
Log Po/w (SILICOS-IT) : 3.72
Consensus Log Po/w : 3.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.33
Solubility : 0.0115 mg/ml ; 0.0000463 mol/l
Class : Moderately soluble
Log S (Ali) : -3.9
Solubility : 0.0315 mg/ml ; 0.000126 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.2
Solubility : 0.00158 mg/ml ; 0.00000635 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.57

Safety of [ 21849-89-8 ]

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

Application In Synthesis of [ 21849-89-8 ]

* 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 [ 21849-89-8 ]
  • Downstream synthetic route of [ 21849-89-8 ]

[ 21849-89-8 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 21849-89-8 ]
  • [ 26608-06-0 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 20, p. 5504 - 5507
  • 2
  • [ 92-66-0 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Nature, 2013, vol. 499, # 7457, p. 192 - 196
  • 3
  • [ 589-87-7 ]
  • [ 108-95-2 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 12, p. 3571 - 3574
  • 4
  • [ 17333-82-3 ]
  • [ 108-95-2 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 270
  • 5
  • [ 589-87-7 ]
  • [ 89466-08-0 ]
  • [ 21849-89-8 ]
YieldReaction ConditionsOperation in experiment
92% With potassium phosphate In 1,4-dioxane; water at 100℃; Intermediate 27 : 4'-Bromo-2-biphenylol1-Bromo-4-iodobenzene (Aldrich, 2 g, 7.07 mmol), (2-hydroxyphenyl)boronic acid (Aldrich, 1.073 g, 7.78 mmol) , Pd(Ph3P) (0.204 g, 0.177 mmol) were dissolved in 1 ,4-dioxane (30 ml_) and water (10 ml_), K3P04 (2.251 g, 10.60 mmol) was added. The reaction mixture was stirred at 100 °C overnight. Solvents were removed under reduced pressure and DCM was added, mixture was washed with water, dried over anhydrous sodium sulfate. Then solvent was removed under reduced pressure to give the title product 4'-bromo-2-biphenylol (1.85 g, 6.54 mmol, 92 percent yield) as brown oil. LCMS: (M+H)+ = 247-249 ; Rt = 3.52 min.
Reference: [1] Patent: WO2012/119978, 2012, A1, . Location in patent: Page/Page column 55
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 17, p. 8068 - 8081
[3] Patent: US2010/81643, 2010, A1, . Location in patent: Page/Page column 44
[4] Patent: WO2010/47982, 2010, A1, . Location in patent: Page/Page column 88
[5] Patent: WO2010/51176, 2010, A1, . Location in patent: Page/Page column 82
[6] Patent: WO2010/51206, 2010, A1, . Location in patent: Page/Page column 82-83
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 9040 - 9052
  • 6
  • [ 1226985-64-3 ]
  • [ 21849-89-8 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogenchloride In 1,4-dioxane; methanol at 90℃; for 24 h; Part C: In a pressure vessel, a solution of Compound 969C (126 mg, 0.33 mmol) in MeOH (5 mL) was treated with hydrogen chloride solution (1.6 mL, 4 M in dioxane). The vessel was stoppered and the reaction mixture was heated with stirring in a 90 0C oil bath for 24 h. The solvents were evaporated and the residue was re-dissolved in MeOH (5 mL). DIPEA (1.2 mL, 859 mg, 6.6 mmol) was added and the reaction mixture was stirred for 3 h. The solvent was removed by rotary evaporation and the residue was purified by sgc (0-30percent EtOAc-hexanes gradient) to afford 75 mg of the desired alcohol 969D as a clear, colorless oil (90percent yield).
Reference: [1] Patent: WO2010/54279, 2010, A1, . Location in patent: Page/Page column 153
  • 7
  • [ 106-37-6 ]
  • [ 89466-08-0 ]
  • [ 21849-89-8 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 20, p. 5504 - 5507
  • 8
  • [ 169691-87-6 ]
  • [ 21849-89-8 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 4, p. 1078 - 1081
  • 9
  • [ 589-87-7 ]
  • [ 95-56-7 ]
  • [ 21849-89-8 ]
Reference: [1] Chemistry Letters, 2007, vol. 36, # 11, p. 1304 - 1305
  • 10
  • [ 92-66-0 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Nature, 2013, vol. 499, # 7457, p. 192 - 196
  • 11
  • [ 589-87-7 ]
  • [ 108-95-2 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 12, p. 3571 - 3574
  • 12
  • [ 533-58-4 ]
  • [ 5467-74-3 ]
  • [ 21849-89-8 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 15, p. 3962 - 3965
  • 13
  • [ 106-37-6 ]
  • [ 21849-89-8 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 4, p. 1078 - 1081
  • 14
  • [ 5720-06-9 ]
  • [ 21849-89-8 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 4, p. 1078 - 1081
  • 15
  • [ 95-56-7 ]
  • [ 21849-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 270
  • 16
  • [ 17333-82-3 ]
  • [ 108-95-2 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 270
  • 17
  • [ 21849-89-8 ]
  • [ 73183-34-3 ]
  • [ 1219741-54-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 17, p. 8068 - 8081
[2] Patent: US2010/81643, 2010, A1, . Location in patent: Page/Page column 44
[3] Patent: WO2010/47982, 2010, A1, . Location in patent: Page/Page column 88
[4] Patent: WO2010/51176, 2010, A1, . Location in patent: Page/Page column 82-83
[5] Patent: WO2010/51206, 2010, A1, . Location in patent: Page/Page column 83
[6] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 9040 - 9052
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