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[ CAS No. 57946-63-1 ] {[proInfo.proName]}

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Chemical Structure| 57946-63-1
Chemical Structure| 57946-63-1
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Product Details of [ 57946-63-1 ]

CAS No. :57946-63-1 MDL No. :MFCD00042150
Formula : C7H5BrF3N Boiling Point : -
Linear Structure Formula :- InChI Key :QKRJIXSZTKOFTD-UHFFFAOYSA-N
M.W : 240.02 Pubchem ID :93899
Synonyms :

Calculated chemistry of [ 57946-63-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.55
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) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 2.82
Log Po/w (WLOGP) : 4.21
Log Po/w (MLOGP) : 3.3
Log Po/w (SILICOS-IT) : 2.81
Consensus Log Po/w : 3.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.41
Solubility : 0.0937 mg/ml ; 0.00039 mol/l
Class : Soluble
Log S (Ali) : -3.02
Solubility : 0.227 mg/ml ; 0.000946 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.78
Solubility : 0.0396 mg/ml ; 0.000165 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 57946-63-1 ]

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 [ 57946-63-1 ]

* 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 [ 57946-63-1 ]
  • Downstream synthetic route of [ 57946-63-1 ]

[ 57946-63-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 544-92-3 ]
  • [ 57946-63-1 ]
  • [ 6526-08-5 ]
YieldReaction ConditionsOperation in experiment
47% at 195℃; for 4 h; Heat a mixture of copper [(1)] cyanide (2.24g, 25.00 mmol), and 2-bromo-4- trifluoromethyl-phenylamine [(5.] [0G,] 20.83 mmol from Avocado) in [ L-METHYL-2-] pyrrolidinone (20 ml) to [195 °C] for four hours. Dilute the reaction mixture with 100 ml of ethyl acetate and wash the dark solution twice with 28percent aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride (brine) and twice with water. Collect the organic layer, dry over sodium sulfate and remove the solvent under reduced pressure. Purify the residue via flash chromatography eluting with a step gradient starting with hexanes and going to 70percent hexanes with 30percent ethyl acetate to obtain 1. [821G] (9.78 mmol, 47percent yield) the title compound as a green amorphous solid: Mass Spectrum (m/e): 187 (M+1).
Reference: [1] Patent: WO2004/14895, 2004, A1, . Location in patent: Page 68
  • 2
  • [ 57946-63-1 ]
  • [ 132839-58-8 ]
YieldReaction ConditionsOperation in experiment
60% at 55℃; for 7 h; This compound was prepared by application of the procedure for oxidation of4-(trifluoromethyl)aniline.[7] A 300 mL three-necked round-bottom flask equipped with a refluxcondenser and a dropping funnel was charged with sodium perborate tetrahydrate (40.69 g, 0.264mol) and glacial acetic acid (50 mL). The dropping funnel was charged with2-bromo-4-(trifluoromethyl)aniline (6.31 g, 26.8 mmol) and glacial acetic acid (50 mL). Thesuspension in the flask was heated to 55°C and the content of the funnel was added dropwise to it.After 3 h, an additional sodium perborate tetrahydrate (20.00 g, 0.130 mol) was added to the reactionmixture and stirred at 55°C for 4 h. The resulting yellow suspension was cooled to room temperatureand filtered through a Celite pad. To the filtrate was added diethyl ether (200 mL) and water (100mL). The organic phase was separated from the mixture and aqueous phase was extracted withdiethyl ether (150 mL x 2). Combined organic phase was neutralized by aqueous sodium hydroxidesolution (3 M) and separated. The separated organic phase was dried over sodium sulfate andconcentrated to afford brown liquid. This crude product was purified by flash columnchromatography (12percent EtOAc/hexane) to give the title compound as a yellow liquid (4.22 g, 60 percent).
Reference: [1] Chemistry Letters, 2018, vol. 47, # 3, p. 296 - 299
  • 3
  • [ 455-14-1 ]
  • [ 57946-63-1 ]
YieldReaction ConditionsOperation in experiment
50% With N-Bromosuccinimide In dichloromethane Add 200 mL of distilled CH2Cl 2 and 4- (trifluoromethyl) aniline (20 g, 124.13 mmol) to a two neck flask. Slowly dropwise N-bromosuccinimide (24.3 g, 136.5 mmol) dissolved in CH2Cl2. When the reaction is complete, extract with CH2Cl2. Purification by column separation (EA: Hx = 1: 4) (yield: 50percent)
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
[2] Patent: KR2018/50795, 2018, A, . Location in patent: Paragraph 0086; 0087; 0104-0106
[3] Patent: US3946025, 1976, A,
[4] Chinese Journal of Chemistry, 2018, vol. 36, # 9, p. 815 - 818
[5] Patent: US3995042, 1976, A,
  • 4
  • [ 455-14-1 ]
  • [ 72678-19-4 ]
  • [ 57946-63-1 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
  • 5
  • [ 887144-94-7 ]
  • [ 615-36-1 ]
  • [ 58458-13-2 ]
  • [ 57946-63-1 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 13, p. 3732 - 3735
  • 6
  • [ 7681-11-0 ]
  • [ 57946-63-1 ]
  • [ 481075-58-5 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With hydrogenchloride; sodium nitrite In water; acetonitrile at -10℃; for 0.5 h;
Stage #2: for 2 h;
The 2-bromo-4 - (trifluoromethyl) aniline (3.00g, 12 . 50mmol) and concentrated hydrochloric acid (15 ml) is added to acetonitrile (30 ml) and water (10 ml) in the mixed solvent, cooling to -10 ° C the rear, to the slowly dropping sodium nitrite (0.95g, 13 . 75mmol) water (5 ml) solution. The resulting reaction mixture into -10 ° C reaction 30 minutes later, to add potassium iodide (2.49g, 15 . 00mmol) water (5 ml) solution, to continue stirring for 2 hours, then thermal insulation to the room temperature reaction sleepovers. After the reaction is ended, is added to the reaction solution of saturated sodium bicarbonate solution (30 ml), and using dichloromethane (50 ml × 3) extraction, the combined organic phase with saturated sodium thiosulfate solution (30 ml) and saturated salt water (30 ml) washing. The separated organic phase is dried with anhydrous sodium sulfate, filter, and concentrating under reduced pressure, the resulting residue is purified by silica gel column chromatography (petroleum ether) to obtain the title compound as a yellow oily liquid (3.95g, 90.0percent).
Reference: [1] Patent: CN105348204, 2016, A, . Location in patent: Paragraph 0386; 0387; 0388
  • 7
  • [ 57946-63-1 ]
  • [ 481075-58-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1726 - 1728
[2] Patent: WO2006/55525, 2006, A2, . Location in patent: Page/Page column 86-87
[3] Patent: WO2004/87156, 2004, A1, . Location in patent: Page/Page column 40
  • 8
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 57946-63-1 ]
  • [ 117324-58-0 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine In dimethyl sulfoxide at 80℃; for 14 - 16 h; Example 139 Synthesis of 5- [Acetyl- (3, 5-bis-trifluoromethyl-benzyl)-amino]-7-trifluoromethyl-2, 3,4, 5- tetrahydro-benzo [b] azepine-1-carboxylic acid tert-butyl ester. Step 1. Preparation of Methyl-3-trifluoromethyl-2-aminobenzoate Add palladium (II) acetate (1.89 g, 8.4 mmol), 1,1- bis (diphenylphosphino) ferrocene (6.83 g, 12.3 mmol), and triethyl amine (32 mL, 44.0 mmol) to a solution of 2-bromo-4-trifluoromethylanaline (10.0 g, 42.0 mmol) in dimethylsulfoxide (283 mL) and methanol (187 mL). At 100 psi of carbon monoxide, heat the mixture to 80 °C. After heating for 14-16 h cool the reaction to room temperature and filter. Dilute the organics with ethyl acetate (500 mL), wash with water (3x200 mL) and brine (200 mL). Dry the organics over sodium sulfate and filter. Remove solvent under vacuum and chromatograph the crude product using ethyl acetate/hexane (10 percent) to elute. This provides the title compound (8.0 g, 88percent) as an off white solid: H NMR (CDC13,400 MHz) 8 3.93 (s, 3H), 6.11 (bs, 2H), 6.73 (d, J = 8.4 Hz, 1H), 7.49 (dd, J = 2.0, 8.4 Hz, 1H), 8.17 (d, J = 2.0 Hz, 1H).
Reference: [1] Patent: WO2005/37796, 2005, A1, . Location in patent: Page/Page column 138
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