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[ CAS No. 189278-27-1 ] {[proInfo.proName]}

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Excepted Quantity USD 0.00
Limited Quantity USD 15-60
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Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
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3d Animation Molecule Structure of 189278-27-1
Chemical Structure| 189278-27-1
Chemical Structure| 189278-27-1
Structure of 189278-27-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 189278-27-1 ]

CAS No. :189278-27-1 MDL No. :MFCD00153087
Formula : C6H3BrF3N Boiling Point : -
Linear Structure Formula :- InChI Key :DOWNSQADAFSSAR-UHFFFAOYSA-N
M.W : 225.99 Pubchem ID :2782902
Synonyms :

Calculated chemistry of [ 189278-27-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.94
TPSA : 12.89 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) : -5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 2.8
Log Po/w (WLOGP) : 4.02
Log Po/w (MLOGP) : 2.33
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 2.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.34
Solubility : 0.103 mg/ml ; 0.000454 mol/l
Class : Soluble
Log S (Ali) : -2.73
Solubility : 0.423 mg/ml ; 0.00187 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0383 mg/ml ; 0.000169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 189278-27-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H301-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 189278-27-1 ]

* 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 [ 189278-27-1 ]
  • Downstream synthetic route of [ 189278-27-1 ]

[ 189278-27-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 68-12-2 ]
  • [ 189278-27-1 ]
  • [ 131747-53-0 ]
Reference: [1] Patent: EP2218711, 2010, A1, . Location in patent: Page/Page column 116
  • 2
  • [ 124-38-9 ]
  • [ 189278-27-1 ]
  • [ 131747-42-7 ]
YieldReaction ConditionsOperation in experiment
35%
Stage #1: With n-butyllithium In hexanes; diethyl ether at -70 - -40℃;
Stage #2: at -70 - 20℃;
Stage #3: With hydrogenchloride In water
Preparation C4:
Synthesis of 6-(trifluoromethyl)picolinic Acid
Preparation C4, Step 1: 2-bromo-6-(trifluoromethyl)-pyridine (100 mg, 0.44 mmol, 1 eq.) was dissolved in diethyl ether at room temperature under nitrogen then cooled to -70° C. Added 1.6M n-Butyllithium in hexanes (0.28 mL, 0.44 mmol, 1 eq.) dropwise via an addition funnel.
Stirred at -40° C. for 15 minutes then cooled to -70° C. and bubbled in CO2 gas for 10 minutes.
Allowed to warm to room temperature.
Added water then rinsed 3 times with diethyl ether.
The aqueous pH was adjusted to=3 with conc. HCl.
Extracted the acidic aqueous layer 3 times with ethyl acetate.
The ethyl acetate layers were combined, dried over sodium sulfate and stripped to give 6-(trifluoromethyl)picolinic acid (30 mg) as a white solid. Yield=35percent. LCMS detects (M+H)+=192.06.
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
[2] Patent: US2005/54626, 2005, A1, . Location in patent: Page/Page column 36
  • 3
  • [ 81290-20-2 ]
  • [ 234111-08-1 ]
  • [ 189278-27-1 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 2, p. 327 - 330
  • 4
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 189278-27-1 ]
  • [ 155377-05-2 ]
YieldReaction ConditionsOperation in experiment
67% at 60℃; for 18 h; Inert atmosphere Step 1:
Methyl 6-trifluoromethyl-pyridine-2-carboxylate
Under the protection of nitrogen gas, to a solution of 2-bromo-6-trifluoromethylpyridine (1.48 g, 6.55 mmol) in methanol (50.0 mL) were successively added palladium acetate (74.0 mg, 0.33 mmol), 1,1'-bis(diphenylphosphino)ferrocene (363.0 mg, 0.655 mmol) and triethylamine (0.92 g, 9.8 mmol), and reacted at a temperature of 60 °C for 18 hours under carbon monoxide atmosphere (2 atm).
After the reaction was complete, the reaction solution was cooled to room temperature, and filtered.
The filtrate was concentrated in vacuo, and the resulting residue was purified by column chromatography on silica gel to afford methyl 6-trifluoromethyl-pyridine-2-carboxylate (0.9 g, yield 67.0percent).
Reference: [1] Patent: EP3330258, 2018, A1, . Location in patent: Paragraph 0077-0078
  • 5
  • [ 189278-27-1 ]
  • [ 887583-52-0 ]
Reference: [1] Patent: US2012/202806, 2012, A1,
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