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[ CAS No. 54396-44-0 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 54396-44-0
Chemical Structure| 54396-44-0
Chemical Structure| 54396-44-0
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Product Details of [ 54396-44-0 ]

CAS No. :54396-44-0 MDL No. :MFCD00153216
Formula : C8H8F3N Boiling Point : -
Linear Structure Formula :- InChI Key :TWLDBACVSHADLI-UHFFFAOYSA-N
M.W : 175.15 Pubchem ID :2735932
Synonyms :

Calculated chemistry of [ 54396-44-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.81
TPSA : 26.02 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) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 2.49
Log Po/w (WLOGP) : 3.76
Log Po/w (MLOGP) : 2.88
Log Po/w (SILICOS-IT) : 2.57
Consensus Log Po/w : 2.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.8
Solubility : 0.278 mg/ml ; 0.00159 mol/l
Class : Soluble
Log S (Ali) : -2.68
Solubility : 0.365 mg/ml ; 0.00208 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.31
Solubility : 0.0862 mg/ml ; 0.000492 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.13

Safety of [ 54396-44-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54396-44-0 ]

* 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 [ 54396-44-0 ]
  • Downstream synthetic route of [ 54396-44-0 ]

[ 54396-44-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 150783-50-9 ]
  • [ 54396-44-0 ]
YieldReaction ConditionsOperation in experiment
98.5% With hydrogenchloride In ethanol Preparation of 2-Methyl-3-Trifluoromethyl-Aniline
A solution of 2,2,2'-trimethyl-3'-trifluoromethyl-propionanilide (10 g.) in 75 ml. ethanol and 75 ml. concentrated HCl was refluxed for 24 hours.
The reaction mixture was then concentrated in vacuo and diluted with water.
It was then basified with 10percent NaOH solution and extracted with ether.
The ether extract was washed with water and brine and dried with MgSO4.
Removal of ether gave a pale brown liquid (6.65 g., 98.5percent) which was purified by distillation under reduced pressure (b.p. 108°-110° C., 30 mm.) to give 5.73 g. of 2-methyl-3-trifluoromethyl-aniline which solidified on standing.
The physical and spectroscopic properties of the product were found to be identical to those of an authentic sample of 2-methyl-3-trifluoromethyl-aniline prepared by the known method below. STR2
Reference: [1] Patent: US5248781, 1993, A,
[2] Heterocycles, 1994, vol. 38, # 10, p. 2243 - 2246
  • 2
  • [ 6656-49-1 ]
  • [ 54396-44-0 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogen In methanol C.
3-Amino-2-Methylbenzotrifluoride
A solution of 2-methyl-3-nitrobenzotrifluoride (41.0 g, 0.2 m) in methanol (100 ml) was stirred under an atmosphere of dry nitrogen at room temperature and palladium on charcoal catalyst (10percent w/w, 1.0 g) was added.
The stirred mixture was warmed to 40°-45° and then hydrogen was passed into the solution at atmospheric pressure until the reduction, as observed by thin-layer chromatography, was complete (4-5 hours).
The solution was cooled to room temperature and the catalyst removed by filtration.
Distillation of the solvent at atmospheric pressure followed by steam distillation of the crude product gave 3-amino-2-methylbenzotrifluoride (32.2 g, 92percent yield), as a pale-brown oil which slowly crystallized.
Reference: [1] Patent: US4831193, 1989, A,
[2] Patent: US4132737, 1979, A,
  • 3
  • [ 62639-16-1 ]
  • [ 54396-44-0 ]
Reference: [1] Patent: US4209464, 1980, A,
[2] Patent: US4172095, 1979, A,
  • 4
  • [ 72763-19-0 ]
  • [ 54396-44-0 ]
Reference: [1] Patent: US4209464, 1980, A,
  • 5
  • [ 62639-16-1 ]
  • [ 7440-66-6 ]
  • [ 54396-44-0 ]
Reference: [1] Patent: US4209464, 1980, A,
  • 6
  • [ 1939-19-1 ]
  • [ 54396-44-0 ]
Reference: [1] Heterocycles, 1994, vol. 38, # 10, p. 2243 - 2246
  • 7
  • [ 98-16-8 ]
  • [ 54396-44-0 ]
Reference: [1] Heterocycles, 1994, vol. 38, # 10, p. 2243 - 2246
  • 8
  • [ 56-23-5 ]
  • [ 95-53-4 ]
  • [ 25449-96-1 ]
  • [ 54396-44-0 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 9, p. 1747 - 1750
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