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[ CAS No. 658-89-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 658-89-9
Chemical Structure| 658-89-9
Chemical Structure| 658-89-9
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Product Details of [ 658-89-9 ]

CAS No. :658-89-9 MDL No. :MFCD03094278
Formula : C7H7F3N2O Boiling Point : -
Linear Structure Formula :- InChI Key :PIOKGAUSPFWRMD-UHFFFAOYSA-N
M.W : 192.14 Pubchem ID :2773959
Synonyms :

Calculated chemistry of [ 658-89-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.93
TPSA : 61.27 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) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.2
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 3.03
Log Po/w (MLOGP) : 1.03
Log Po/w (SILICOS-IT) : 0.98
Consensus Log Po/w : 1.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.39
Solubility : 0.776 mg/ml ; 0.00404 mol/l
Class : Soluble
Log S (Ali) : -2.74
Solubility : 0.352 mg/ml ; 0.00183 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.943 mg/ml ; 0.00491 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 658-89-9 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H317-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 658-89-9 ]

* 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 [ 658-89-9 ]
  • Downstream synthetic route of [ 658-89-9 ]

[ 658-89-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 2267-23-4 ]
  • [ 658-89-9 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With hydrogenchloride; tin(ll) chloride In ethanol at 70 - 80℃; for 0.5 h;
Stage #2: With sodium hydroxide In ethanol at 0 - 5℃;
A solution of 2-nitro-4-trifluoromethoxy-phenylamine 1 (25.0 g, 0.112 mol) in EtOH (200 ml) was added to solution of stannous chloride dihydrate (82.0 g, 0.363 mol) in cone HCl (330 ml) . The resulting suspension was stirred for 0.5 h at 70-80°C, cooled at 0-5°C, and basified to pH=ll-12 by 40percent NaOH solution, and the product extracted with ether (2x200 ml) . The organic solution was washed with water, dried over Na24 and evaporated to dryness under reduced pressure to give the title compound as a brown oil (21.1 g, 98percent).
92% With hydrogen In ethanol for 48 h; EXAMPLE 61; 1 -(7H-Pyrro lor2,3-dlpyrimidin-4-yl)-4-(5-(trifluoromethoxy)-lH-benzordlimidazo 1-2- vDpiperidin-4-amine6 IA. 4-(trifluoromethoxy)benzene- 1 ,2-diamine 2-Nitro-4-(trifluoromethoxy)aniline (2.000 g, 9.00 mmol) and palladium (0.096 g, 0.90 mmol) were dissolved in ethanol (25 mL) and stirred under a balloon of hydrogen for 48 hours. The reaction was filtered and evaporated to dryness to afford 4-(trifluoromethoxy)- benzene-l,2-diamine (1.392 g, 7.24 mmol, 92 percent) as a black oil; m/z (ESI+) (M+H)+ = ; HPLC tR = 1.53 min. IH NMR (400.132 MHz, CDC13) δ 3.41 (4H, vbrs), 6.60 - 6.58 (2H, m), 6.67 (IH, d).
86% With hydrogen In ethanol at 20℃; 2-nitro-4-trifluoromethoxy-phenylamine Compound 16a (0.5 g, 2.25 mmol) was dissolved into EtOH (30 mL) and Raney Ni (~ 0.5 g, prewashed with EtOH) was added. The mixture was shaken in a Parr shaker under H2 (50 psi) at room temperature overnight, filtered through Celite and the solvent was evaporated to dryness to provide 4-trifluoromethoxy-benzene-l,2-diamine Compound 16b (0.373 g, yield 86percent) as. a red- brown semi-solid.
Reference: [1] Patent: WO2006/50148, 2006, A2, . Location in patent: Page/Page column 38
[2] Patent: WO2008/75109, 2008, A1, . Location in patent: Page/Page column 160
[3] Patent: WO2006/130673, 2006, A1, . Location in patent: Page/Page column 115
[4] Patent: WO2006/22954, 2006, A2, . Location in patent: Page/Page column 24
[5] Patent: US2014/315963, 2014, A1, . Location in patent: Paragraph 0228
[6] Patent: WO2008/129007, 2008, A1, . Location in patent: Page/Page column 42
  • 2
  • [ 2267-22-3 ]
  • [ 658-89-9 ]
YieldReaction ConditionsOperation in experiment
93% With hydrogen In ethanol at 20℃; for 16 h; Inert atmosphere Example 23
2-(2,4-Difluorophenyl)-1,1-difluoro-3-(1H-tetrazol-1-yl)-1-(6-(trifluoromethoxy)quinoxalin-2-yl)propan-2-ol (54)
To a stirred solution of 2-nitro-5-(trifluoromethoxy)aniline (5.0 g, 22.5 mmol) in EtOH (50 mL) was added 10percent Pd/C (1.2 g) under inert atmosphere.
The resulting reaction mixture was stirred for 16 h at RT under H2 atmosphere.
After consumption of the starting material (by TLC), the reaction mixture was filtered through a pad of Celite.(R). and washed with EtOAc (3*50 mL).
The filtrate was concentrated under reduced pressure to afford compound AW (4.0 g, 20.83 mmol, 93percent) as an orange syrup. 1H NMR (500 MHz, DMSO-d6): δ 6.50-6.45 (m, 2H), 6.29 (d, J=8.0 Hz, 1H), 4.76-4.75 (br s, 4H). MS (ESI): m/z 194 [M+2]+.
Reference: [1] Patent: US2012/329802, 2012, A1, . Location in patent: Page/Page column 36-37
  • 3
  • [ 1351534-05-8 ]
  • [ 658-89-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8541 - 8554
  • 4
  • [ 461-82-5 ]
  • [ 658-89-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8541 - 8554
  • 5
  • [ 1737-06-0 ]
  • [ 658-89-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8541 - 8554
  • 6
  • [ 787-57-5 ]
  • [ 658-89-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8541 - 8554
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