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[ CAS No. 16499-52-8 ] {[proInfo.proName]}

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Chemical Structure| 16499-52-8
Chemical Structure| 16499-52-8
Structure of 16499-52-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 16499-52-8 ]

CAS No. :16499-52-8 MDL No. :MFCD09264505
Formula : C8H3F3N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FHFVTHPGDCWXTD-UHFFFAOYSA-N
M.W : 216.12 Pubchem ID :26343877
Synonyms :

Calculated chemistry of [ 16499-52-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.98
TPSA : 69.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 1.86
Log Po/w (WLOGP) : 3.64
Log Po/w (MLOGP) : 1.33
Log Po/w (SILICOS-IT) : 0.72
Consensus Log Po/w : 1.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.52
Solubility : 0.659 mg/ml ; 0.00305 mol/l
Class : Soluble
Log S (Ali) : -2.94
Solubility : 0.246 mg/ml ; 0.00114 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.76
Solubility : 0.377 mg/ml ; 0.00175 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.09

Safety of [ 16499-52-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16499-52-8 ]

* 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.

  • Downstream synthetic route of [ 16499-52-8 ]

[ 16499-52-8 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 16499-52-8 ]
  • [ 16499-68-6 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
  • 2
  • [ 402-14-2 ]
  • [ 151-50-8 ]
  • [ 16499-52-8 ]
YieldReaction ConditionsOperation in experiment
(i) NaNO2, aq. HCl, (ii) /BRN= 4652394/, aq. CuSO4; Multistep reaction;
  • 3
  • [ 16499-52-8 ]
  • [ 16499-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. H2SO4 2: H2 / Pd-C
792 mg With water; hydrazine hydrate In ethanol at 45℃; for 3h; Reflux; 10.1 Step 1 Step 1 To a solution of 2-nitro-5-(trifluoromethyl)aniline (5.00 g, 24.3 mmol) and concentrated hydrochloric acid (6.1 mL) in water (50 mL) was added dropwise under ice-cooling, an aqueous solution (15 mL) of sodium nitrite (1.84 g, 26.7 mmol), and the mixture was stirred at room temperature for 1 hr. Insoluble material was filtered off and to the obtained filtrate under ice-cooling, an aqueous solution (20 mL) of copper cyanide (2.91 g, 29.2 mmol) and sodium cyanide (600 mg, 12.2 mmol) was added dropwise. Toluene (9 mL) was added, and the mixture was stirred at room temperature for 15 hrs. The reaction mixture was diluted with chloroform. The mixture was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The obtained concentrated residue was suspended in ethanol (100 mL), and hydrazine monohydrate (2.43 g, 48.6 mmol) was added. While heating the mixture to 45° C., Raney Ni (1.2 g) was added in several times, and the mixture was stirred at 60° C. for 1 hr. and heated under reflux for 2 hrs. After allowing to cool to room temperature, insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The obtained concentrated residue was dissolved in ethyl acetate, and the mixture was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (33-50% ethyl acetate/hexane) to give 2-amino-5-trifluoromethylbenzamide as a brown powder (792 mg, 16% for 2 steps).
  • 4
  • [ 773837-37-9 ]
  • [ 402-14-2 ]
  • [ 16499-52-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-nitro-5-(trifluoromethyl)aniline With hydrogenchloride; sodium nitrite In water at 35℃; for 1h; Cooling with ice; Stage #2: sodium cyanide With copper(l) cyanide In water; toluene at 35℃; for 15h; Cooling with ice; 10.1 Step 1 Step 1 To a solution of 2-nitro-5-(trifluoromethyl)aniline (5.00 g, 24.3 mmol) and concentrated hydrochloric acid (6.1 mL) in water (50 mL) was added dropwise under ice-cooling, an aqueous solution (15 mL) of sodium nitrite (1.84 g, 26.7 mmol), and the mixture was stirred at room temperature for 1 hr. Insoluble material was filtered off and to the obtained filtrate under ice-cooling, an aqueous solution (20 mL) of copper cyanide (2.91 g, 29.2 mmol) and sodium cyanide (600 mg, 12.2 mmol) was added dropwise. Toluene (9 mL) was added, and the mixture was stirred at room temperature for 15 hrs. The reaction mixture was diluted with chloroform. The mixture was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The obtained concentrated residue was suspended in ethanol (100 mL), and hydrazine monohydrate (2.43 g, 48.6 mmol) was added. While heating the mixture to 45° C., Raney Ni (1.2 g) was added in several times, and the mixture was stirred at 60° C. for 1 hr. and heated under reflux for 2 hrs. After allowing to cool to room temperature, insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The obtained concentrated residue was dissolved in ethyl acetate, and the mixture was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (33-50% ethyl acetate/hexane) to give 2-amino-5-trifluoromethylbenzamide as a brown powder (792 mg, 16% for 2 steps).
  • 5
  • [ 16499-52-8 ]
  • ethyl ((2-(aminocarbonyl)-4-trifluoromethylphenyl)amino)(oxo)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water; hydrazine hydrate / ethanol / 3 h / 45 °C / Reflux 2: triethylamine / tetrahydrofuran / 2 h / 35 °C / Calcination
  • 6
  • [ 16499-52-8 ]
  • ethyl 4-oxo-6-trifluoromethyl-3,4-dihydroquinazoline-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: water; hydrazine hydrate / ethanol / 3 h / 45 °C / Reflux 2: triethylamine / tetrahydrofuran / 2 h / 35 °C / Calcination 3: sodium ethanolate / ethanol / 1 h / 35 °C / Cooling with ice
  • 7
  • [ 1176723-57-1 ]
  • [ 16499-52-8 ]
YieldReaction ConditionsOperation in experiment
78% With copper diacetate; urea; trifluoroacetic acid In dimethyl sulfoxide at 110℃;
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