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[ CAS No. 76041-79-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 76041-79-7
Chemical Structure| 76041-79-7
Chemical Structure| 76041-79-7
Structure of 76041-79-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 76041-79-7 ]

CAS No. :76041-79-7 MDL No. :MFCD12546486
Formula : C6H3BrF3NO Boiling Point : -
Linear Structure Formula :- InChI Key :OPLCXLXORZDTMX-UHFFFAOYSA-N
M.W : 241.99 Pubchem ID :13491780
Synonyms :

Calculated chemistry of [ 76041-79-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.96
TPSA : 33.12 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) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.41
Log Po/w (WLOGP) : 3.72
Log Po/w (MLOGP) : 2.08
Log Po/w (SILICOS-IT) : 2.6
Consensus Log Po/w : 2.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.16
Solubility : 0.166 mg/ml ; 0.000688 mol/l
Class : Soluble
Log S (Ali) : -2.75
Solubility : 0.433 mg/ml ; 0.00179 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.19
Solubility : 0.154 mg/ml ; 0.000638 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 76041-79-7 ]

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 [ 76041-79-7 ]

* 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 [ 76041-79-7 ]
  • Downstream synthetic route of [ 76041-79-7 ]

[ 76041-79-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 22245-83-6 ]
  • [ 76041-79-7 ]
YieldReaction ConditionsOperation in experiment
80% at 80℃; Step 1 : 5-Bromo-3-(trifluoromethyl)pyridin-2(1 - )-one (P45a) To a solution of 3-(trifluoromethyl)pyridin-2(1 /-/)-one (25.0 g, 0.15 mol) in AcOH (300 mL) were added NaOAc (15.1 g, 0.18 mol) and dropwise Br2 (8.6 mL, 0.17 mol). Then the mixture was stirred at 80°C overnight, concentrated, diluted with sat aq. NaHC03 and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2S04, filtered, concentrated and purified by CC (PE/EA = 7/2) to give compound P45a (29.7 g, 80percent) as a white solid.
14 g With N-Bromosuccinimide; oxygen In tetrahydrofuran at 20℃; for 4 h; To a solution of 3-(trifluoromethyl)-2(1H)-pyridinone (D15) (10 g) in tetrahydrofuran (THF) (100 mL) stirred in air at room temperature was added NBS (14.19 g) portionwise. The reaction mixture was stirred for 4 h, then diluted with water (100 mL), extracted with ethyl acetate (3*50 mL). The combined organic phases were dried over sodium sulphate and concentrated to give 5-bromo-3-(trifluoromethyl)-2(1H)-pyridinone (D16) (14 g) as yellow solid. MS (ES): C6H3BrF3NO requires 241; found 242.0 (M+H+).
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 16, p. 6106 - 6122
[2] Patent: WO2012/139775, 2012, A1, . Location in patent: Page/Page column 69-70
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6578 - 6581
[4] Patent: US2013/12491, 2013, A1, . Location in patent: Paragraph 0171; 0172
  • 2
  • [ 13466-38-1 ]
  • [ 2926-30-9 ]
  • [ 76041-79-7 ]
YieldReaction ConditionsOperation in experiment
60% With H2O8S2*2H3N; C42H34F10IrN4(1+)*F6P(1-) In dimethyl sulfoxide at 40℃; for 0.5 h; Flow reactor; UV-irradiation General procedure: In an oven-dried vial equipped with a magnetic stirrer and a PTFE septum, [Ir{dF(CF3)ppy}2](dtbpy)]PF6 (5.6 mg, 1 molpercent) was added to a mixture of the substrate (0.5 mmol, 1 equiv), CF3SO2Na (1.5 mmol, 3 equiv), and (NH4)2S2O8 (0.5 mmol, 1 equiv) in DMSO (5 mL). The solution was pumped into the Vapourtec photoreactor (fluoropolymer tube, 1.3 mm i.d., 10 mL) and the liquid flowrate was set at 0.33 mL/min (30 min residence time). The reactor was irradiated with 54 blue LEDs (450 nm, total power 24 W). The reaction mixture collected from the outlet was diluted with H2O and extracted with Et2O (3×). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The crude was then pre-adsorbed onto silica, dried in vacuo, and purified by flash chromatography to yield the trifluoromethylated product.
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 22, p. 4978 - 4985
  • 3
  • [ 65753-47-1 ]
  • [ 76041-79-7 ]
Reference: [1] Patent: US2013/12491, 2013, A1,
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