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[ CAS No. 175278-09-8 ] {[proInfo.proName]}

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Chemical Structure| 175278-09-8
Chemical Structure| 175278-09-8
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Product Details of [ 175278-09-8 ]

CAS No. :175278-09-8 MDL No. :MFCD00179338
Formula : C7H5BrF3NO Boiling Point : -
Linear Structure Formula :- InChI Key :QVILSWLYJYMGRN-UHFFFAOYSA-N
M.W : 256.02 Pubchem ID :737382
Synonyms :

Calculated chemistry of [ 175278-09-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.23
TPSA : 35.25 ?2

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) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 3.11
Log Po/w (WLOGP) : 4.2
Log Po/w (MLOGP) : 2.37
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 2.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.6
Solubility : 0.0649 mg/ml ; 0.000253 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.0775 mg/ml ; 0.000303 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.52
Solubility : 0.077 mg/ml ; 0.000301 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.74

Safety of [ 175278-09-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P280-P301+P310 UN#:2810
Hazard Statements:H301-H317-H412 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 175278-09-8 ]

* 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 [ 175278-09-8 ]

[ 175278-09-8 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 175278-09-8 ]
  • [ 87-13-8 ]
  • C15H15BrF3NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 135℃; for 2h; EXAMPLE 122 N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-8-(trifluoromethoxy)-3-quinolinecarboxamide [] A mixture of <strong>[175278-09-8]4-bromo-2-trifluoromethoxyaniline</strong> (10.0 g) and diethyl ethoxymethylenemalonate (7.9 mL) is heated to 135 C for 2 h. The reaction mixture is diluted with diphenylether (90 mL) and heated to reflux with removal of ethanol by a Dean-Start trap for 30 min. The resulting precipitate is poured into heptane and filtered to afford 10.83 g (73%) of the 6-bromo-8-trifluoromethoxyquinoline ethyl ester. A mixture of the quinoline ethyl ester (5.0 g) and 4-chlorobenzylamine (12.0 mL) are heated to 190 C for 1 h. The mixture is diluted with toluene (25 mL), allowed to cool to rt, and filtered. The crude product is recrystallized (HOAc, water) to afford 5.03 g (80%) of the amide. The resulting amide (469 mg), bis(triphenylphosphine)palladium (II) chloride (175 mg), and triethylamine (5.0 mL) are dissolved in DMF (50 mL). Propargyl alcohol (2.5 mL) is added over 20 h at 90 C. The reaction mixture was allowed to cool to rt, poured into aq. ammonium chloride (200 mL) and extracted with ethyl acetate (4 x 50 mL). The organic layer is washed with sat. aqueous brine (10 mL). The aqueous layer is back-extracted with ethyl acetate (20 mL). The combined organic layers are dried (MgSO4) and concentrated. The crude product is purified by column chromatography (dichloromethane/ methanol, 100/1; 50/1; 100/3) to afford 580 mg (26%) of the title compound as a white solid. Physical characteristics are as follows: Mp 262 C dec.1H NMR (DMSO-d6) delta 12.89, 10.12, 8.64, 8.20, 7.86, 7.42-7.34, 5.42, 4.55, 4.35.13C NMR (CF3CO2D) delta 175.7, 167.4, 144.1, 139.1, 134.8, 133.3, 131.5, 129.2, 129.1, 127.3, 126.3, 123.6, 123.2, 120.6, 107.3, 84.8, 84.1, 55.5, 44.1.IR (drift) 1936 (w), 1657 (s), 1602, 1574, 1544, 1517 (s), 1279 (s), 1268, 1223 (s), 1212 (s), 1183, 1161 (s), 1048, 1020, 802 cm-1.MS (ESI-) m/z 449 (M-H)-.Anal. Found for C21H14ClF3N2O4: C, 55.86; H, 3.16; N, 6.09; Cl, 7.96
  • 2
  • [ 175278-09-8 ]
  • [ 126747-14-6 ]
  • [ 885477-08-7 ]
YieldReaction ConditionsOperation in experiment
38% With sodium carbonate;5%-palladium/activated carbon; In methanol; water; at 70℃; for 12h; Step 1: A mixture of <strong>[175278-09-8]4-bromo-2-(trifluoromethoxy)benzenamine</strong> (512 mg, 2.0 mmol), 4-cyanophenylboronic acid (324 mg, 2.2 mmol), 5% activated palladium on carbon (50% wet, 100 mg) and sodium carbonate (424 mg, 4.0 mmol) in a mixture of methanol:water (20 mL, 1:1) was heated at 70 C. for 12 hours. The reaction mixture was filtered through a celite pad and the filtrate evaporated to give a crude residue. Purification on silica gel using a mixture of ethyl acetate:hexane (4:1) as eluant gave the light yellow solid 4-amino-3-trifluoromethoxy-biphenyl-4-carbonitrile (210 mg, 38% yield).
  • 3
  • [ 175278-09-8 ]
  • 4-bromo-1-chloro-2-(trifluoromethyloxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% NaNO2 (2.43 g, 0.035 mol) in water (10 mL) was added in portions over 30 min to <strong>[175278-09-8]4-bromo-2-trifluoromethoxyaniline</strong> (9 g, 35 mmol) in a mixture of HCl (aq, cone, 25 mL) and water (25 mL) at (0-2 0C). The mixture was stirred at 0-2 0C for 15 min and CuCl (6 g, 61 mmol) in HCl (aq, cone, 10 mL) was added dropwise. After 10 min at rt, the mixture was heated at reflux for 15 min. Steam-distillation followed by extraction (CH2Cl2), drying (Na2SO4) of the distillate followed by concentration and distillation (bp 82-84 0C at 20 Torr) gave 3.86 g (40%) of the sub-title compound.
40% NaNO2 (2.43 g, 0.035 mol) in water (10 mL) was added in portions over 30 min to <strong>[175278-09-8]4-bromo-2-trifluoromethoxyaniline</strong> (9g, 35 mmol) in a mixture of HCl (aq, cone,25 mL) and water (25 mL) at (0-2 0C). The mixture was stirred at 0-2 0C for 15 min and CuCl (6 g, 61 mmol) in HCl (aq, cone, 10 mL) was added dropwise. After EPO <DP n="136"/>10 min at it, the mixture was heated at reflux for 15 min. Steam-distillation followed by extraction (CHoCl2), drying (Na2SO4) of the distillate followed by concentration and distillation (bp 82-840C at 20 Torrj gave 3.86 g (40%) of the sub-title compound.
With copper dichloride; isopentyl nitrite; In acetonitrile; at 70℃; for 3h; A mixture of isoamyl nitrite (4 mL, 30 mmol), copper (II) chloride (3.22 g, 24 mmol) and <strong>[175278-09-8]4-bromo-2-(trifluoromethoxy)aniline</strong> (Compound 30A) (5.1 g, 20 mmol) in acetonitrile (80 mL) was heated at 70 C for 3 hours. The mixture was poured into an aqueous HC1 solution (0.5 M, 50 mL) and extracted with ethyl acetate (50 mL x 2). The combined extracts were washed with water (50 mL x 4) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (petroleum ether) to afford Compound 30B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used. ?H-NIVIR (DMSO-d6, 400 IVII{z): 5 (ppm) 7.33-7.3 5 (m, 1H), 7.37-7.40 (m, 1H), 7.48 (t, J= 1.6 Hz, 1H).
  • 4
  • [ 175278-09-8 ]
  • [ 7447-39-4 ]
  • 4-bromo-1-chloro-2-(trifluoromethyloxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tert.-butylnitrite; In acetonitrile; EXAMPLE 23A 4-bromo-1-chloro-2-(trifluoromethoxy)benzene A mixture of tert-butyl nitrite (1.78 mL, 15.0 mmol), copper (II) chloride (1.61 g, 12.0 mmol) and <strong>[175278-09-8]4-bromo-2-(trifluoromethoxy)aniline</strong> (2.56 g, 10.0 mmol) in acetonitrile (40 mL) was heated to 70 C., stirred for 3 hours, cooled to room temperature, poured into 0.5M HCl, and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 275 (M+H)+.
With tert.-butylnitrite; In acetonitrile; Example 23A 4-bromo-1-chloro-2-(trifluoromethoxy)benzene A mixture of tert-butyl nitrite (1.78 mL, 15.0 mmol), copper (II) chloride (1.61 g, 12.0 mmol) and <strong>[175278-09-8]4-bromo-2-(trifluoromethoxy)aniline</strong> (2.56 g, 10.0 mmol) in acetonitrile (40 mL) was heated to 70 C., stirred for 3 hours, cooled to room temperature, poured into 0.5M HCl, and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 275 (M+H)+.
  • 5
  • [ 175278-09-8 ]
  • [ 87-13-8 ]
  • [ 228728-40-3 ]
YieldReaction ConditionsOperation in experiment
10.83 g (73%) EXAMPLE 122 N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-8-(trifluoromethoxy)-3-quinolinecarboxamide STR160 A mixture of <strong>[175278-09-8]4-bromo-2-trifluoromethoxyaniline</strong> (10.0 g) and diethyl ethoxymethylenemalonate (7.9 mL) is heated to 135 C. for 2 h. The reaction mixture is diluted with diphenylether (90 mL) and heated to reflux with removal of ethanol by a Dean-Start trap for 30 min. The resulting precipitate is poured into heptane and filtered to afford 10.83 g (73%) of the 6-bromo-8-trifluoromethoxyquinoline ethyl ester.
  • 6
  • [ 860617-71-6 ]
  • [ 175278-09-8 ]
  • 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium fluoride;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In tetrahydrofuran; hexane; for 16h; <strong>[175278-09-8]4-Bromo-2-(trifluoromethoxy)aniline</strong> (1.3 g, 5.0 mmol), 5-cyano-1-methyl-1H-pyrrol-2-yl boronic acid (0.9 g, 6.0 mmol), potassium fluoride (0.96 g, 16.5 mmol), and tris(dibenzylideneacetone)dipalladium (0.12 g, 0.12 mmol) were placed in an oven dried flask under nitrogen and THF (12.5 mL) was added. Tri-t-butylphosphine (10 wt % in hexane) (0.356 mL, 0.24 mol) was added and the reaction was stirred for 16 hours. The reaction mixture was filtered through silica, rinsed with ethyl acetate, and concentrated. The crude product was pre-adsorbed onto the Celite reagent and purified via Isco chromatography (the Redisep column, silica, gradient 5-30% ethyl acetate in hexane) to afford 1.0 g (71%) of 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile. HPLC purity 98.2% at 210-370 nm, 9.6 min.; the Xterra RP18 instrument, 3.5%, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (Ammon. Form. Buff. PH=3.5/ACN+MeOH) for 10 min., hold 4 min. MS (ES) m/z 281.
71% tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In tetrahydrofuran; hexane; for 16h; Example 58 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile <strong>[175278-09-8]4-Bromo-2-(trifluoromethoxy)aniline</strong> (1.3 g, 5.0 mmol), 5-cyano-1-methyl -1H-pyrrol-2-ylboronic acid (0.9 g, 6.0 mmol), potassium fluoride (0.96 g, 16.5 mmol), and tris(dibenzylideneacetone)dipalladium (0.12 g, 0.12 mmol) were placed in an oven dried flask under nitrogen and THF (12.5 mL) was added. Tri-t-butylphosphine (10 wt % in hexane) (0.356 mL, 0.24 mol) was added and the reaction was stirred for 16 hours. The reaction mixture was filtered through silica, rinsed with ethyl acetate, and concentrated. The crude product was pre-adsorbed onto the Celite reagent and purified via Isco chromatography (the Redisep column, silica, gradient 5-30% ethyl acetate in hexane) to afford 1.0 g (71%) of 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile. HPLC purity 98.2% at 210-370 nm, 9.6 min.; the Xterra RP18 instrument, 3.5mu, 150*4.6 mm column, 1.2 mL/min., 85/15-5/95 (Ammon. Form. Buff. PH=3.5/ACN+MeOH) for 10 min., hold 4 min. MS (ES) m/z 281.
  • 8
  • [ 175278-09-8 ]
  • [ 2252-44-0 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; sodium nitrite; In water; isopropyl alcohol;Product distribution / selectivity; 1b. Preparation of 1 -bromo-3-trifluoromethoxybenzene. 2579.53 g of 2-propanol and 1100 g of the product from stage Ia are placed in a 10 litre lined glass reactor with 4 necks and outlet on bottom, and a previously prepared solution of 382.52 g of NaNO2 in 766.18 g of water is added. 459.6 g of concentrated sulphuric acid are then metered slowly. The acids are diluted and the upper organic phase is separated from the lower aqueous phase. The organic phase is washed and a first organic phase and an upper aqueous phase are separated. The latter is further diluted with water until a second organic phase is released. This organic phase is added to the first and everything is washed again, separating an aqueous phase and an organic phase which, after being anhydrified with CaCl2, undergoes distillation to provide the product indicated in the title (final yield 84%). B.p. 156-158C/760 mmHg.
  • 9
  • [ 1535-75-7 ]
  • [ 175278-09-8 ]
YieldReaction ConditionsOperation in experiment
1a. Preparation of 4-bromo-2-trifluoromethoxyaniline (formula (IIIa). 3462 g of acetic acid and 1700 g of 2-trifluoromethoxyaniline are placed at room temperature in a 10 1 lined glass reactor with 4 necks, outlet on bottom, thermostat with brine cryostat, provided with mechanical agitation, bubble condenser and thermometer; the mixture is subsequently cooled to 0-5C and 1894.26 g of NBS are added, maintaining the temperature at 0-50C. At the end of the reaction the mixture is brought back to room temperature and the acetic acid is eliminated by distillation. The residue is washed with water, the phases are separated, the organic phase is neutralised with NaHCCbeta and the phases are separated again, the inorganic phase is washed with water and the product indicated in the title is isolated. B.p. 115C/30 mmHg.
With N-Bromosuccinimide; acetic acid; at 0 - 20℃; To a solution of 2-(trifluoromethoxy)aniline (318A) (2.655 mg, 15 mmol) in acetic acid (6 mL) was added NBS (2.94 g, 16.5 mmol) at 0 C and stirred at room temperature overnight. It was concentrated under reduced pressure. The residue was diluted with ethyl acetate (100 mL), washed with water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 20% v/v) to afford Compound 318B. LC-MS (ESI) m/z: 256 [M +H]+; 'H-NMR (CDCb, 400 MHz): d (ppm) 3.89 (s, 2H), 6.67 (d, J= 8.8 Hz, 1H), 7.18 (dd, J= 8.8, 2.4 Hz, 1H), 7.28 (d, J= 2.4 Hz, 1H).
  • 10
  • [ 109-01-3 ]
  • [ 175278-09-8 ]
  • [ 1034732-96-1 ]
YieldReaction ConditionsOperation in experiment
70% With lithium hexamethyldisilazane; DavePhos;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; for 1h;Inert atmosphere; Reflux; Tris(dibenzilideneacetone)dipalladium (1.1 g, 1.2 mmol), 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)-biphenyl (0.94 g, 2.4 mmol), <strong>[175278-09-8]4-bromo-2-trifluoromethoxy-phenylamine</strong> (30.7 g, 120 mmol) in THF (50 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. LiN(TMS)2 solution (1 M in THF, 288 mL) and N-methylpiperazine (26.7 mL, 194 mmol) were added and the reaction refluxed for 1 h. The reaction mixture was then allowed to cool to room temperature and filtered through a pad of celite. The organic phase was concentrated, the residue dissolved in DCM (200 ml) and washed with water (1 x 100 ml). The organic phases were dried over anhydrous Na?SCM, the solvent evaporated in vacuo and the crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 23 g of 4-(4-methyl-piperazin-1-yl)-2- trifluoromethoxy-phenylamine (70% yield) as a light brown powder. MS calc: 276.1318; MS found: 276.1320
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; ;