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[ CAS No. 220801-66-1 ] {[proInfo.proName]}

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Chemical Structure| 220801-66-1
Chemical Structure| 220801-66-1
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Product Details of [ 220801-66-1 ]

CAS No. :220801-66-1 MDL No. :MFCD07778484
Formula : C9H9BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WDMIWHBNMUBGHF-UHFFFAOYSA-N
M.W : 245.07 Pubchem ID :10657986
Synonyms :

Calculated chemistry of [ 220801-66-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.03
TPSA : 46.53 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) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 2.09
Log Po/w (SILICOS-IT) : 2.24
Consensus Log Po/w : 2.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.91
Solubility : 0.303 mg/ml ; 0.00124 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.352 mg/ml ; 0.00144 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.16
Solubility : 0.169 mg/ml ; 0.000689 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 220801-66-1 ]

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 [ 220801-66-1 ]

* 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 [ 220801-66-1 ]
  • Downstream synthetic route of [ 220801-66-1 ]

[ 220801-66-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 614-75-5 ]
  • [ 220801-66-1 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 18 h; 2-(2-hydroxyphenyl)acetic acid (484 g, 3.18 mol) was dissolved in methanol, and then tetrabutylammonium tribromide (1549 g, 3.18 mol) was added to the solution. The resulting mixture was allowed to stir at room temperature for 18 hours. After evaporation of solvent in vacuo, the residue obtained was dissolved in EtOAc. The organic layer was washed with 1 N HC1, water and brine, dried and concentrated, the residue obtained was purified using flash column chromatography on silica gel (eluted with PE / EtOAc = 10 / 1) to give pure methyl 2-(5-bromo-2-hydroxyphenyl)acetate (750 g, 94percent). 1H- MR (400 MHz, CDC13) δ 7.48 (br s, 1H), 7.20-7.25 (m, 2H), 6.75-6.78 (m, 1H), 3.74 (s, 3H), 3.62 (s, 2H). MS (M+H)+: 245.
90% at 20℃; for 18 h; 2-(2-hydroxyphenyl)acetic acid (100 g, 0.66 mol) was dissolved in MeOH, and then TBATB (320 g, 0.66 mmol) was added to the solution. The resulting mixture was stirred at RT for 18 hours. After evaporation of solvent, the residue was dissolved in diethyl ether. The organic layer was washed with 1 N HC1, 2 M sodium bisulfate, H20 and brine, dried and evaporated to yield methyl 2-(5-bromo-2-hydroxyphenyl)acetate (145 g, yield: 90percent) 1H-NMR (400 MHz, CDCl3) δ 7.48 (br s, 1H), 7.20-7.25 (m, 2H), 6.75-6.78 (m, 1H), 3.74 (s, 3H), 3.62 (s, 2H). MS (M+H)+: 245.
Reference: [1] Patent: WO2011/106986, 2011, A1, . Location in patent: Page/Page column 38; 39
[2] Patent: WO2011/106929, 2011, A1, . Location in patent: Page/Page column 79
[3] ChemMedChem, 2017, vol. 12, # 17, p. 1436 - 1448
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 1, p. 164 - 172
[5] Patent: WO2013/134562, 2013, A1, . Location in patent: Paragraph 00109
[6] Patent: WO2014/99503, 2014, A1, . Location in patent: Paragraph 00104
[7] Patent: WO2015/35059, 2015, A1, . Location in patent: Paragraph 00105
[8] Bioorganic and Medicinal Chemistry Letters, 2018,
  • 2
  • [ 22446-37-3 ]
  • [ 220801-66-1 ]
Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 7, p. 1227 - 1238
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