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[ CAS No. 474024-36-7 ] {[proInfo.proName]}

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Chemical Structure| 474024-36-7
Chemical Structure| 474024-36-7
Structure of 474024-36-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 474024-36-7 ]

CAS No. :474024-36-7 MDL No. :MFCD03094308
Formula : C9H5BrF3N Boiling Point : -
Linear Structure Formula :- InChI Key :RYUZTTSDBHOIAF-UHFFFAOYSA-N
M.W :264.04 Pubchem ID :2778436
Synonyms :

Calculated chemistry of [ 474024-36-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.67
TPSA : 23.79 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) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 3.15
Log Po/w (WLOGP) : 4.69
Log Po/w (MLOGP) : 3.51
Log Po/w (SILICOS-IT) : 3.85
Consensus Log Po/w : 3.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.65
Solubility : 0.0596 mg/ml ; 0.000226 mol/l
Class : Soluble
Log S (Ali) : -3.32
Solubility : 0.127 mg/ml ; 0.000479 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.63
Solubility : 0.0062 mg/ml ; 0.0000235 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.76

Safety of [ 474024-36-7 ]

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 [ 474024-36-7 ]

* 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.

  • Downstream synthetic route of [ 474024-36-7 ]

[ 474024-36-7 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 474024-36-7 ]
  • [ 40138-16-7 ]
  • [ 1005346-89-3 ]
YieldReaction ConditionsOperation in experiment
90% With caesium carbonate In ethanol; toluene at 150℃; for 0.166667h; microwave irradiation;
  • 2
  • [ 67-56-1 ]
  • [ 474024-36-7 ]
  • [ 1069115-04-3 ]
YieldReaction ConditionsOperation in experiment
92% With sulfuric acid at 0℃; Reflux;
  • 3
  • [ 474024-36-7 ]
  • [ 74-88-4 ]
  • [ 1393491-75-2 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2-(2-bromo-4-(trifluoromethyl)phenyl)acetonitrile With potassium <i>tert</i>-butylate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0℃; for 0.166667h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0 - 10℃; for 1.16667h; Inert atmosphere;
98% Stage #1: 2-(2-bromo-4-(trifluoromethyl)phenyl)acetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 0.166667h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 25℃; for 3h;
98% Stage #1: 2-(2-bromo-4-(trifluoromethyl)phenyl)acetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.166667h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;
Stage #1: 2-(2-bromo-4-(trifluoromethyl)phenyl)acetonitrile With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran for 12h; Inert atmosphere;

  • 4
  • [ 474024-36-7 ]
  • [ 1360451-40-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / dimethyl sulfoxide; mineral oil / 12 h / 20 °C 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / N,N-dimethyl-formamide / 1 h 2.2: 18 h / 80 °C 3.1: potassium fluoride / methanol / 16 h / 20 °C / Inert atmosphere
  • 5
  • [ 474024-36-7 ]
  • [ 1360449-50-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / dimethyl sulfoxide; mineral oil / 12 h / 20 °C 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / N,N-dimethyl-formamide / 1 h 2.2: 18 h / 80 °C 3.1: potassium fluoride / methanol / 16 h / 20 °C / Inert atmosphere 4.1: copper(l) iodide; triethylamine / acetonitrile / 0.17 h 4.2: 0.5 h / 80 °C 5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 30 °C / 15001.5 Torr 6.1: butan-1-ol / 21 h / 120 °C
  • 6
  • [ 474024-36-7 ]
  • [ 1360451-39-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / dimethyl sulfoxide; mineral oil / 12 h / 20 °C 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / N,N-dimethyl-formamide / 1 h 2.2: 18 h / 80 °C
  • 7
  • [ 474024-36-7 ]
  • [ 1360451-41-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / dimethyl sulfoxide; mineral oil / 12 h / 20 °C 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / N,N-dimethyl-formamide / 1 h 2.2: 18 h / 80 °C 3.1: potassium fluoride / methanol / 16 h / 20 °C / Inert atmosphere 4.1: copper(l) iodide; triethylamine / acetonitrile / 0.17 h 4.2: 0.5 h / 80 °C
  • 8
  • [ 474024-36-7 ]
  • [ 1360451-42-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / dimethyl sulfoxide; mineral oil / 12 h / 20 °C 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / N,N-dimethyl-formamide / 1 h 2.2: 18 h / 80 °C 3.1: potassium fluoride / methanol / 16 h / 20 °C / Inert atmosphere 4.1: copper(l) iodide; triethylamine / acetonitrile / 0.17 h 4.2: 0.5 h / 80 °C 5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 30 °C / 15001.5 Torr
  • 9
  • [ 474024-36-7 ]
  • [ 1777-03-3 ]
  • [ 1360451-32-6 ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: 2-(2-bromo-4-(trifluoromethyl)phenyl)acetonitrile With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 2-triethylsilylacetylene at 80℃; for 1h; 1 1) 2-(2-((Triethylsilyl)ethynyl)-4-(trifluoromethyl)phenyl)acetonitrile 1) 2-(2-((Triethylsilyl)ethynyl)-4-(trifluoromethyl)phenyl)acetonitrile Bis(triphenylphosphine)palladium(II) chloride (0.106 g, 0.151 mmol), copper(I) iodide (0.058 g, 0.303 mmol) and triphenylphospine (0.079 g, 0.303 mmol) are dissolved in a mixture of i-Pr2NH (11.36 ml)/DMF (3.79 ml) (degassed with N2 for 15 min). 2-(2-Bromo-4-(trifluoromethyl)phenyl)acetonitrile (1.1 g, 3.8 mmol) is added to the resultant orange solution. The mixture is stirred at RT for one hour. Triethyl(ethynyl)silane (1.018 ml, 5.68 mmol) is added dropwise, and the batch is warmed to 80° C. After 1 hour, a saturated, aqueous NH4Cl solution (50 ml) is added to the strongly dark-coloured batch. After phase separation, the aqueous phase is extracted three times with 50 ml of ethyl acetate each time. The combined organic phases are dried over Na2SO4 and evaporated to dryness in vacuo. The residue is purified by chromatography on silica gel with a 98:2 mixture of petroleum ether and ethyl acetate, giving 2-(2-((triethylsilyl)ethynyl)-4-(trifluoromethyl)phenyl)acetonitrile (orange oil, 91%, 1.226 g, 3.79 mmol); 1H NMR (DMSO-d6) δ [ppm] J [Hz]:7.80-7.89 (m, 2H) 7.73-7.79 (m, 1H) 4.17 (s, 2H) 1.04 (t, 9H) 0.62-0.81 (m, 6H).
  • 10
  • [ 474024-36-7 ]
  • [ 109-64-8 ]
  • [ 1360451-37-1 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 12h; 1 1) (4-Trifluoromethylphenyl)cyclobutanecarbonitrile Sodium hydride (380 mg; 9.5 mmol; content 60%) is suspended in 4 ml of DMSO. 1,3-Dibromopropane (920 mg; 4.5 mmol) and (2-bromo-4-trifluoromethylphenyl)carbonitrile are dissolved in 10 ml of DMSO and added dropwise to the sodium hydride suspension. The batch is stirred at RT for 12 h. 10 ml of water are then added, and the mixture is extracted to exhaustion with ethyl acetate. Conventional further work-up and purification on silica gel (petroleum ether/ethyl acetate=95:5) gives (4-trifluoromethylphenyl)cyclobutanecarbonitrile (965 mg, 84%); 1H NMR (DMSO-d6) δ [ppm] J [Hz]: 8.09 (d, 1H), 7.85 (dd, 1H), 7.68 (d, 1H), 2.81-3.03 (m, 2H), 2.65-2.81 (m, 2H), 2.18-2.44 (m, 1H), 1.82-2.00 (m, 1H).
  • 11
  • [ 474024-36-7 ]
  • 6-(trifluoromethyl)benzo[b]thiophen-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; Sodium thiosulfate pentahydrate; caesium carbonate In ethylene glycol; N,N-dimethyl-formamide at 140℃; for 12h; Sealed tube; Inert atmosphere;
  • 12
  • [ 474024-36-7 ]
  • [ 5977-87-7 ]
  • 2-(p-tolyl)-6-[(trifluoromethyl)benzo[b]thiophene]-3-carbonitirle [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium phosphate; copper(l) iodide; trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 5h;
  • 13
  • [ 474024-36-7 ]
  • [ 5874-09-9 ]
  • 2-(4-methoxyphenyl)-6-(trifluoromethyl)benzo[b]thiophene-3-carbonitirle [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium phosphate; copper(l) iodide; trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 5h;
  • 14
  • [ 474024-36-7 ]
  • [ 5990-17-0 ]
  • 2-(4-chlorophenyl)-6-(trifluoromethyl)benzo[b]thiophene-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With potassium phosphate; copper(l) iodide; trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 6.5h;
  • 15
  • [ 474024-36-7 ]
  • [ 5969-47-1 ]
  • 2-(4-fluorophenyl)-6-(trifluoromethyl)benzo[b]thiophene-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium phosphate; copper(l) iodide; trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 5.5h;
  • 16
  • [ 2168-83-4 ]
  • [ 474024-36-7 ]
  • 2-(thiophenyl-2-yl)-6-(trifluoromethyl)benzo[b]thiophene-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium phosphate; copper(l) iodide; trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 5.5h;
  • 17
  • [ 474024-36-7 ]
  • [ 74-88-4 ]
  • 2-[2-bromo-4-(trifluoromethyl)phenyl]propanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: 2-(2-bromo-4-(trifluoromethyl)phenyl)acetonitrile With sodium hexamethyldisilazane In tetrahydrofuran; hexane for 0.0833333h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere;
  • 18
  • [ 474024-36-7 ]
  • [ 75-03-6 ]
  • 2-[2-bromo-4-(trifluoromethyl)phenyl]butanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: 2-(2-bromo-4-(trifluoromethyl)phenyl)acetonitrile With sodium hexamethyldisilazane In tetrahydrofuran; hexane for 0.0833333h; Inert atmosphere; Stage #2: ethyl iodide In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere;
  • 19
  • [ 474024-36-7 ]
  • C10H8BrF3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 0.08 h / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 5 h / -78 - 20 °C / Inert atmosphere
  • 20
  • [ 474024-36-7 ]
  • methyl (Z)-4-[2-bromo-4-(trifluoromethyl)phenyl]-2-[(tert-butoxycarbonyl)amino]pent-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 0.08 h / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 5 h / -78 - 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 - 20 °C
  • 21
  • [ 474024-36-7 ]
  • methyl (Z)-4-[2-bromo-4-(trifluoromethyl)phenyl]-2-[(tert-butoxycarbonyl)amino]hex-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 0.08 h / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 5 h / -78 - 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 - 20 °C
  • 22
  • [ 474024-36-7 ]
  • 1-(tert-butyl) 2-methyl 4-methyl-7-(trifluoromethyl)quinoline-1,2(2H)-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 0.08 h / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 5 h / -78 - 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 - 20 °C 4.1: caesium carbonate; dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) / toluene / 1 h / 150 °C / Inert atmosphere; Microwave irradiation
  • 23
  • [ 474024-36-7 ]
  • 1-(tert-butyl) 2-methyl 4-ethyl-7-(trifluoromethyl)quinoline-1,2(2H)-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 0.08 h / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 5 h / -78 - 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 - 20 °C 4.1: caesium carbonate; dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) / toluene / 1 h / 150 °C / Inert atmosphere; Microwave irradiation
  • 24
  • [ 474024-36-7 ]
  • 1-cyclohexyl-2,4,6-triphenylpyridin-1-ium tetrafluoroborate salt [ No CAS ]
  • 2-(2-cyclohexyl-4-(trifluoromethyl)phenyl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With nickel(II) bromide dimethoxyethane; manganese; 4,4'-Dimethoxy-2,2'-bipyridin In 1-methyl-pyrrolidin-2-one at 45℃; for 20h; Inert atmosphere; chemoselective reaction;
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