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[ CAS No. 749258-95-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 749258-95-5
Chemical Structure| 749258-95-5
Chemical Structure| 749258-95-5
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Quality Control of [ 749258-95-5 ]

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Product Details of [ 749258-95-5 ]

CAS No. :749258-95-5 MDL No. :MFCD20488934
Formula : C5H3F3N2O Boiling Point : -
Linear Structure Formula :- InChI Key :HAKAYTVRYJYKGH-UHFFFAOYSA-N
M.W : 164.09 Pubchem ID :22508459
Synonyms :

Calculated chemistry of [ 749258-95-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.86
TPSA : 45.75 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) : -7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.85
Log Po/w (XLOGP3) : 0.18
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 0.97
Log Po/w (SILICOS-IT) : 2.12
Consensus Log Po/w : 1.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.31
Solubility : 8.07 mg/ml ; 0.0492 mol/l
Class : Very soluble
Log S (Ali) : -0.7
Solubility : 32.8 mg/ml ; 0.2 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.44
Solubility : 0.6 mg/ml ; 0.00366 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 749258-95-5 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 749258-95-5 ]

* 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 [ 749258-95-5 ]

[ 749258-95-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 749258-94-4 ]
  • [ 749258-95-5 ]
YieldReaction ConditionsOperation in experiment
78% With bromine In acetic acid at 50℃; 73.e e) 4-TRIFLUOROMETHVLPYRIDAZIN-3 (2H)-one A solution of bromine (4.26 ml, 36.1 mmol) in glacial acetic acid (20 ml) was added dropwise to a stirred solution of the product of step d) (6.0 g, 36.1 mmol) in glacial acetic acid (80 ml) whilst maintaining the temperature of the mixture at ~50 C. The mixture was cooled to room temperature and concentrated to dryness. The residue was diluted with toluene and concentrated to dryness again. The crude product was purified by flash chromatography on silica gel in 40: 1 DCM: MeOH to give a brown solid (4.6 g, 78%). IH NMR (400 MHz, DMSO) 8 13.77 (1 H, s), 8. 07 (1 H, d, J = 4.3 Hz), 7.88 (1 H, dd, J = 0. 8,4. 0 HZ) ppm.
  • 2
  • [ 749258-95-5 ]
  • [ 749258-96-6 ]
YieldReaction ConditionsOperation in experiment
61% With N,N-dimethyl-formamide; trichlorophosphate at 120℃; for 2h; Intermediate 49b: 3-chloro-4-(trifluoromethyl)pyridazine [00514] Intermediate 49b: 3-chloro-4-(trifluoromethyl)pyridazine[00515] To a solution of 5-(trifluoromethyl)-1H-pyridazin-6-one (0.76g, 4.64mmol) in phosphorus oxychloride (4.33mL, 46.44mmol) was added a drop of N,N-dimethylformamide. The mixture washeated to 120 °C for 2 hours. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was diluted with EtOAc (lOOmL) and washed with water (lOOmL) and brine (lOOmL). The organic layer was dried over Na2504 and concentrated in vacuoto give 3-chloro-4-(trifluoromethyl)pyridazine (0.51g, 2.82mmol, 61% yield) as a brown oil which was used in the next step without further purification.MS Method 2: RT: 1.29 mi mlz 182.9 [M+H]
34% With trichlorophosphate for 1.5h; Heating / reflux; 3 A mixture of 4-(trifluoromethyl)pyridazin-3(2H)-one (9.3 g, 56.7 mmol) in POCI3 (75 mL) was heated at reflux for 1.5 h. The solvent was removed and the resulting material was carefully neutralized with saturated aqueous NaHCOβ and then with solidK2CO3 (using ethyl acetate to reduce foaming). The mixture was extracted with ethyl acetate. The combined organics were washed with brine and dried over MgSOφ The product was purified via silica gel chromatography eluting with a 5:95 to 30:70 E:H gradient to afford the title compound as an orange liquid (3.51 g, 34%).
  • 3
  • [ 444689-44-5 ]
  • [ 749258-95-5 ]
YieldReaction ConditionsOperation in experiment
77% With hydrazine In ethanol at 20℃; for 3h; Heating / reflux; 2 Ethyl 2-hydroxy-4-oxo-2-(trifluoromethyl)butanoate (16.62 g, 78 mmol) in EtOH (40 mL) was treated with hydrazine hydrate (5.66 mL, 116 mmol) and stirred at room temperature for 1.5 h, then heated at reflux for 1.5 h. The ethanol was removed in vacuo and the resulting material was partitioned between water and ethyl acetate and the layers were separated. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were dried over MgSC>4 and concentrated in vacuo to yield the title compound as a yellow/orange solid (9.75 g, 77%).
0.76 g With hydrazine hydrate In ethanol for 4h; Reflux; Intermediate 49a: 5-(trifluoromethyl)-1 H-pyridazin-6-one [00512] Intermediate 49a: 5-(trifluoromethyl)-1 H-pyridazin-6-one[00513] To a solution of ethyl 3,3,3-trifluoropyruvate (2.OmL, 15.Ogmmol) and acetaldehyde(0.85mL, 15.Ogmmol) in DCM (25mL) was added L-proline (677mg, 5.88mmol). The reaction mixture was stirred at room temperature for 2 hours. Water (5OmL) was then added and extracted with DCM (3 x 5OmL). The combined organic layers were washed with brine (1 OOmL), dried over Na2SO4 and concentrated in vacuo to give ethyl 2-hydroxy-4-oxo-2-(trifluoromethyl)butanoate. This was then dissolved in EtCH (25mL) and hydrazine hydrate (0.92mL, 18.91 mmol) added. Themixture was stirred at reflux for 4 hours. The mixture was then cooled to room temperature and concentrated in vacuo and the resulting residue was diluted with EtOAc (1 OOmL) and washed with water (1 OOmL). The aqueous layer was extracted with EtOAc (3 x 1 OOmL) and the combined organic layers were washed with brine (lOOmL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography using an eluent of 50 % EtOAc in heptane to give5-(trifluoromethyl)-1H-pyridazin-6-one (0.76g, 4.64mmol, 37% yield) as an orange oil. MS Method 2: RT: 0.86 mi mlz 164.7 [M+H]
  • 4
  • [ 749258-95-5 ]
  • diethyl 2-[4-(trifluoromethyl)pyridazin-3-yl]propanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate; N,N-dimethyl-formamide / 2 h / 120 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: Reflux
  • 5
  • [ 749258-95-5 ]
  • lithium 2-[4-(trifluoromethyl)pyridazin-3-yl]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate; N,N-dimethyl-formamide / 2 h / 120 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: Reflux 3.1: lithium hydroxide / methanol; water / 20 - 60 °C
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