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[ CAS No. 174603-55-5 ] {[proInfo.proName]}

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Chemical Structure| 174603-55-5
Chemical Structure| 174603-55-5
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Product Details of [ 174603-55-5 ]

CAS No. :174603-55-5 MDL No. :MFCD06656907
Formula : C9H8BrFO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VHFQIJJCQTZKFK-UHFFFAOYSA-N
M.W : 247.06 Pubchem ID :10922852
Synonyms :

Calculated chemistry of [ 174603-55-5 ]      Expand+

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 : 50.45
TPSA : 37.3 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) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 2.47
Log Po/w (WLOGP) : 3.03
Log Po/w (MLOGP) : 3.11
Log Po/w (SILICOS-IT) : 2.99
Consensus Log Po/w : 2.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.21 mg/ml ; 0.000848 mol/l
Class : Soluble
Log S (Ali) : -2.9
Solubility : 0.313 mg/ml ; 0.00127 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.72
Solubility : 0.0473 mg/ml ; 0.000191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 174603-55-5 ]

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 [ 174603-55-5 ]

* 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 [ 174603-55-5 ]
  • Downstream synthetic route of [ 174603-55-5 ]

[ 174603-55-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 174603-55-5 ]
  • [ 174603-56-6 ]
YieldReaction ConditionsOperation in experiment
970 mg at 60 - 80℃; for 18 h; Inert atmosphere Under argon 3-(2-bromo-4-fluorophenyl)propanoic acid (1 .2 g) is added in small portions to trifluoromethanesulfonic acid (15 mL) at room temperature. The mixture is stirred for 2 hours at 60°C and for 16 hours at 80°C. After cooling to room temperature the mixture is poured slowly in ice-water. The aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated aqueous Na2CO3 solution and brine. After drying (MgSO4) the solvent is evaporated. The residue is stirred with dichloromethane (40 ml_), filtered and washed with dichloromethane. The combined dichloromethane phases are concentrated to give the title compound. Yield: 970 mg; LC (method 3): tR = 0.60 min; Mass spectrum (ESI+): m/z = 229 [M+H]+.
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
[2] Patent: WO2013/144098, 2013, A1, . Location in patent: Page/Page column 114; 115
[3] Patent: WO2015/36759, 2015, A1,
  • 2
  • [ 174603-54-4 ]
  • [ 174603-55-5 ]
YieldReaction ConditionsOperation in experiment
33% for 4.5 h; Reflux To a mixture of 2-(2-bromo-4-fluoro-benzyl)-malonic acid diethyl ester (2.1 g, 6.07 mmol)and water (14 mL) was added potassium hydroxide (0.68 g, 12.14 mmol) and the reactionmixture was heated under reflux for 4.5h. The reaction mixture was cooled to RT and theethanol removed in vacuo. The aqueous residue was cooled to 0 00, acidified with conc.H2S04, and heated at 120 00 for 16h. The reaction mixture was cooled to 0 00 theprecipitated solid was collected by filtration, washed with water and dried to obtain 3-(2-bromo-4-fluoro-phenyl)-propionic acid as an off-white solid (0.5 g, 33percent).R: 0.2 (30percent EtOAc/pet-ether).1H NMR (400MHz, DMSO-d6): O 12.26 (5, 1H), 7.55-7.52 (m, 1H), 7.42-7.38 (m, 1H),7.23-7.18 (m, 1H), 2.90 (t, J= 7.8 Hz, 2H), 2.52 (t, J= 7.8 Hz, 2H).
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
[2] Patent: WO2015/36759, 2015, A1, . Location in patent: Page/Page column 171
  • 3
  • [ 61150-57-0 ]
  • [ 174603-55-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
[2] Patent: WO2015/36759, 2015, A1,
  • 4
  • [ 1422-53-3 ]
  • [ 174603-55-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
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