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[ CAS No. 93249-62-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 93249-62-8
Chemical Structure| 93249-62-8
Chemical Structure| 93249-62-8
Structure of 93249-62-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 93249-62-8 ]

CAS No. :93249-62-8 MDL No. :MFCD00075249
Formula : C8H5F3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :WQUZBERVMUEJTD-UHFFFAOYSA-N
M.W : 206.12 Pubchem ID :1268058
Synonyms :

Calculated chemistry of [ 93249-62-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.54
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.47
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : 3.36
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 2.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.55
Solubility : 0.584 mg/ml ; 0.00283 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.424 mg/ml ; 0.00206 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.4
Solubility : 0.813 mg/ml ; 0.00394 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 93249-62-8 ]

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 [ 93249-62-8 ]

* 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 [ 93249-62-8 ]
  • Downstream synthetic route of [ 93249-62-8 ]

[ 93249-62-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 145742-65-0 ]
  • [ 93249-62-8 ]
YieldReaction ConditionsOperation in experiment
81% With boron tribromide In dichloromethane at -20 - 0℃; for 2 h; Inert atmosphere [00244] Step A: BBr3 (85.2 g, 341 mmol) was added dropwise at -20°C under N2 to a solution of 2-methoxy-5-(trifluoromethoxy)benzaldehyde (50.0 g, 227 mmol) in DCM (500 mL). The reaction mixture was stirred at 0°C for 2 hours. The reaction mixture was worked up by adding ice chips, then the mixture was poured into saturated aqueous NaHC03 (300 mL), and extracted with DCM (3 X 400 mL). The combined organic layers were dried and concentrated to afford the crude product, which was purified by silica gel (hexanes: EtOAc = 20:1) to give 2- hydroxy-5-(trifluoromethoxy)benzaldehyde (38.0 g, 81.0percent yield). NMR (400MHz, CDC13) δ 10.97 (s, 1H), 9.87 (s, 1H), 7.43-7.38 (m, 2H), 7.02 (d, J = 8.0 Hz, 1 H).
Reference: [1] Patent: WO2013/148851, 2013, A1, . Location in patent: Paragraph 00244
[2] Patent: US2014/275172, 2014, A1, . Location in patent: Paragraph 0842
  • 2
  • [ 828-27-3 ]
  • [ 93249-62-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 12, p. 3162 - 3165
[2] Patent: US6034256, 2000, A,
  • 3
  • [ 710-18-9 ]
  • [ 93249-62-8 ]
Reference: [1] Patent: US2014/275172, 2014, A1,
  • 4
  • [ 896732-42-6 ]
  • [ 68-12-2 ]
  • [ 93249-62-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 12, p. 3162 - 3165
  • 5
  • [ 50-00-0 ]
  • [ 828-27-3 ]
  • [ 93249-62-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 73, p. 177 - 186
  • 6
  • [ 93249-62-8 ]
  • [ 74-88-4 ]
  • [ 145742-65-0 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With potassium carbonate In DMF (N,N-dimethyl-formamide) for 0.5 h;
(Step 1) A 25 ml round-bottomed flask was charged with 1.0 g (4.85 mmol) of 2-hydroxy-5-(trifluoromethoxy)benzaldehyde, 8ml of dimethylformamide (DMF) and 738 mg (5.34 mmol) of potassium carbonate, the mixture was stirred for about 30 minutes, and then a solution of methyl iodide 758 mg (5.34 mmol)/DMF 2 ml was added thereto under ice-cooling. The mixture was stirred under ice-cooling for 1 hour and then at room temperature for 19 hours. To the reaction mixture was added 20 ml of ethyl acetate and 20 ml of water, the mixture was shaken and the organic layer was separated. The aqueous layer was extracted once again with 20 ml of ethyl acetate, and the organic layers were combined, and washed twice with 20 ml of water and then twice with 20 ml of brine. The organic layer was dried over MgSO4 (anhydrous) and concentrated under reduced pressure to obtain 1.0 g of 2-methoxy-5-(trifluoromethoxy)benzaldehydel (yield: 93percent).1H-NMR (CDCl3) δ: 3.96 (s, 3H), 7.02 (d, 1H, J=8.8Hz), 7.41 (d, 1H, J=9.2Hz), 7.69(1H, s, ), 10.44(1H, s).
Reference: [1] Patent: EP1460062, 2004, A1, . Location in patent: Page 70
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