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[ CAS No. 138526-69-9 ] {[proInfo.proName]}

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Product Details of [ 138526-69-9 ]

CAS No. :138526-69-9 MDL No. :MFCD00070738
Formula : C6H2BrF3 Boiling Point : -
Linear Structure Formula :- InChI Key :HKJCELUUIFFSIN-UHFFFAOYSA-N
M.W : 210.98 Pubchem ID :611409
Synonyms :

Calculated chemistry of [ 138526-69-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.02
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -5.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 3.02
Log Po/w (WLOGP) : 4.13
Log Po/w (MLOGP) : 4.33
Log Po/w (SILICOS-IT) : 3.8
Consensus Log Po/w : 3.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.49
Solubility : 0.0675 mg/ml ; 0.00032 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.436 mg/ml ; 0.00207 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.09
Solubility : 0.017 mg/ml ; 0.0000805 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 138526-69-9 ]

Signal Word:Danger Class:3
Precautionary Statements:P501-P273-P202-P240-P210-P233-P201-P243-P241-P242-P264-P280-P370+P378-P391-P308+P313-P362+P364-P303+P361+P353-P332+P313-P305+P351+P338+P310-P403+P235-P405 UN#:1993
Hazard Statements:H315-H318-H351-H411-H226 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 138526-69-9 ]

* 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 [ 138526-69-9 ]
  • Downstream synthetic route of [ 138526-69-9 ]

[ 138526-69-9 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 1489-53-8 ]
  • [ 138526-69-9 ]
YieldReaction ConditionsOperation in experiment
94.6% With sodium hypochlorite; sodium dihydrogenphosphate; sodium bromide In dichloromethane; water at 8 - 15℃; for 2.66667 h; The preparation method of 3,4,5-trifluorobromobenzene is as follows:(1) Add 1 mol of 1,2,3-trifluorobenzene and 3 mol of dichloromethane to a 2 L reaction flask.Stir the solution into a solution and cool to 8-12 ° C;(2) dissolving 1.0 mol of sodium bromide and 120 g of sodium dihydrogen phosphate in water,Formulated into an aqueous solution, cooled to 12 ° C and added to the reaction bottle of step (1);(3) 10percent sodium hypochlorite solution (1.2 mol sodium hypochlorite content) was added dropwise to the reaction flask at 15 ° C, the dropping process was carried out for 100 min, and the temperature reaction was maintained for 60 min;(4) After standing and phase separation, the organic phase is washed to neutral,Calcium chloride is dried and the organic phase is desolvated to obtain crude 3,4,5-trifluorobromobenzene;(5) melt recrystallization of crude 3,4,5-trifluorobromobenzene at -25 ° C,200 g of the product 3,4,5-trifluorobromobenzene were obtained in a yield of 94.6percent and a content of 99.5percent.
Reference: [1] Patent: CN108947763, 2018, A, . Location in patent: Paragraph 0020-0040
[2] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[3] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[4] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[5] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[6] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[7] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
  • 2
  • [ 17299-95-5 ]
  • [ 138526-69-9 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[2] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[3] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
  • 3
  • [ 17299-94-4 ]
  • [ 138526-69-9 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
  • 4
  • [ 176317-02-5 ]
  • [ 138526-69-9 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[2] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[3] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
  • 5
  • [ 530145-56-3 ]
  • [ 138526-69-9 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[2] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[3] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
  • 6
  • [ 530145-55-2 ]
  • [ 138526-69-9 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[2] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[3] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
  • 7
  • [ 34628-01-8 ]
  • [ 138526-69-9 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
  • 8
  • [ 163733-96-8 ]
  • [ 138526-69-9 ]
Reference: [1] Journal of Physical Chemistry A, 2000, vol. 104, # 2, p. 352 - 361
  • 9
  • [ 121-43-7 ]
  • [ 138526-69-9 ]
  • [ 143418-49-9 ]
Reference: [1] Zeitschrift fur Anorganische und Allgemeine Chemie, 2002, vol. 628, # 13, p. 2827 - 2833
[2] Patent: US2011/105766, 2011, A1, . Location in patent: Page/Page column 4
  • 10
  • [ 5419-55-6 ]
  • [ 138526-69-9 ]
  • [ 143418-49-9 ]
Reference: [1] Journal of Organometallic Chemistry, 2000, vol. 598, # 1, p. 127 - 135
  • 11
  • [ 138526-69-9 ]
  • [ 143418-49-9 ]
Reference: [1] Patent: EP1191008, 2002, A1, . Location in patent: Page 71
  • 12
  • [ 124-38-9 ]
  • [ 138526-69-9 ]
  • [ 121602-93-5 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 447 - 451
[2] Journal of Physical Chemistry A, 2000, vol. 104, # 2, p. 352 - 361
  • 13
  • [ 138526-69-9 ]
  • [ 134227-45-5 ]
Reference: [1] Patent: EP2151432, 2010, A1, . Location in patent: Page/Page column 53
  • 14
  • [ 544-92-3 ]
  • [ 138526-69-9 ]
  • [ 134227-45-5 ]
Reference: [1] Patent: WO2007/49728, 2007, A1, . Location in patent: Page/Page column 162-163
[2] Patent: WO2007/49729, 2007, A2, . Location in patent: Page/Page column 106
  • 15
  • [ 138526-69-9 ]
  • [ 170112-66-0 ]
YieldReaction ConditionsOperation in experiment
70% With iodine; magnesium In tetrahydrofuran at 0 - 20℃; for 2.5 h; magnesium (5.76g, 237mmol) in tetrahydrofuran (190ml) to iodine (10.0mg, 40.0μmol) was added, 3, 4,5-trifluoro-bromobenzene (50.0g, 237mmol) was slowly added dropwise at room temperature.After the mixture was stirred at the same temperature for 30 minutes, iodine (66.1g, 261mmol) in tetrahydrofuran solution (160ml) of was added at 0 , and the mixture was stirred for 2 hours at room temperature.The reaction mixture was poured into ice water and extracted with hexane after neutralization with concentrated hydrochloric acid.The extract was washed with a saturated aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The concentrate was purified by silica gel column chromatography and purified by (elution solvent ethyl acetate / n-hexane = 1/10) to give the title compound yellow oil (yield 45.0 g, 70percent yield).
70% With iodine; magnesium In tetrahydrofuran at 0 - 20℃; for 2.5 h; Magnesium (5.76g, 237mmol) tetrahydrofran soln. (190 ml) iodine (10.0 mg, 40. 0μmol) is added, 3, 4, 5-trifluorolactic bromobenzene (50.0g, 237mmol) dropped slowly at room temperature. After 30 minutes at the same temperature, iodine (66.1g, 261mmol) by adding a 0 °C tetrahydrofran soln. (160 ml), 2 hours at room temperature. The reaction mixture is poured into the ice, and then neutralized with hydrochloric Phenylbicyclohexane hyperchromic extracted. The extract is washed with saturated aqueous sodium thiosulfate, after drying with anhydrous sodium sulfate, a vacuum concentrator. Concentrated silica gel column chromatography (elution solvent: ethyl acetate/n-hexane = 1/10) by, for compd. yellow oilies (yield 45.0g, yield 70percent) is obtained.
70% With iodine; magnesium In tetrahydrofuran at 0 - 20℃; for 2.5 h; Method for preparing 3,4,5-trifluoroiodobenzene Magnesium (5.76 g, 237 mmol)In tetrahydrofuran (190 ml) was added iodine (10.0 mg, 40.0 μmol)After adding 3,4,5-trifluorobromobenzene (50.0 g, 237 mmol)Was slowly added dropwise at room temperature. After stirring at the same temperature for 30 minutes,Iodine (66.1 g, 261 mmol)Of tetrahydrofuran solution (160 ml)Was added at 0 ° C.,And the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water,After neutralization with concentrated hydrochloric acid, it was extracted with hexane. The extract was washed with saturated aqueous sodium thiosulfate solution,After drying with anhydrous sodium sulfate,And concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/10),To give the title compound as a yellow oil (yield 45.0 g, yield 70percent). 1 H NMR spectrum (CDCl3) .sigma .: 7.32 (2H, t, J = 6.4 Hz).
70% With iodine; magnesium In tetrahydrofuran at 20℃; for 2.5 h; After adding iodine (10.0 mg, 40.0 μmol) to a tetrahydrofuran solution (190 ml) of magnesium (5.76 g, 237 mmol), 3,4,5-trifluorobromobenzene (50.0 g, 237 mmol) was added at room temperature Was slowly added dropwise.After stirring at the same temperature for 30 minutes, a tetrahydrofuran solution (160 ml) of iodine (66.1 g, 261 mmol) was added at 0 ° C., and the mixture was stirred at room temperature for 2 hours.The reaction mixture was poured into ice water, neutralized with concentrated hydrochloric acid, and extracted with hexane. The extract was washed with saturated aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/10) to give the title compound as a yellow oil (yield 45.0 g, yield 70percent).

Reference: [1] Patent: JP2016/84346, 2016, A, . Location in patent: Paragraph 0050
[2] Patent: JP2016/84328, 2016, A, . Location in patent: Paragraph 0187
[3] Patent: JP2016/84347, 2016, A, . Location in patent: Paragraph 0136
[4] Patent: JP2016/84348, 2016, A, . Location in patent: Paragraph 0064
[5] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2002, vol. 373, p. 17 - 24
  • 16
  • [ 67-56-1 ]
  • [ 138526-69-9 ]
  • [ 261762-35-0 ]
YieldReaction ConditionsOperation in experiment
92% at 60℃; for 6 h; Large scale In a 3000 L reactor, 201.6 kg of KOH was added,Pumped 253.2 kg of 3,4,5-trifluorobromobenzene and 1500 L of methanol,Close the reaction kettle, stirring up to 60 ,After 6 hours of reaction,Raw materials have been basically complete.The material into the crystallization pot with nitrogen into the pot,Stirring and cooling to -5 ° C,Insulation 5h filter,To give 2,3-difluoro-5-bromoanisole,Yield 92.0percentContent of 99.2percent. The methanol recovery in the filtrate can be reused.
Reference: [1] Patent: CN106478377, 2017, A, . Location in patent: Paragraph 0037; 0038; 0053; 0054; 0055; 0056; 0061; 0062
  • 17
  • [ 108-24-7 ]
  • [ 138526-69-9 ]
  • [ 220141-73-1 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5 h;
Stage #2: With copper(l) chloride In tetrahydrofuran; toluene at 0℃; for 1 h;
of magnesium (3.53 g, 145 mmol) in tetrahydrofuran (100ml) iodine (361 mg, 1.42 mmol) was added, 3, 4,5-trifluoro-bromobenzene (30.0g, 142mmol) was slowly added dropwise at room temperature.After the mixture was stirred at the same temperature for 30 minutes, the solution of copper (I) (704mg, 7.11mmol) chloride and acetic anhydride (16.0g, 156mmol) was added at 0 in toluene solution (100ml) of, at the same temperature and the mixture was stirred for 1 hour.The reaction mixture was poured into 2N aqueous hydrochloric acid and extracted with toluene.The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The concentrate was purified by silica gel column chromatography and purified by (elution solvent ethyl acetate / n-hexane = 1/10) to give the title compound yellow oil (yield 21.0 g, 85percent yield).
85%
Stage #1: With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5 h;
Stage #2: With copper(l) chloride In tetrahydrofuran; toluene at 0℃; for 1 h;
Magnesium (3.53g, 145mmol) tetrahydrofran soln. (100 ml) in after iodinating (361 mg, 1.42mmol), 3, 4, 5-trifluorolactic bromobenzene (30.0g, 142mmol) dropped slowly at room temperature. After 30 minutes at the same temperature, the solution is a copper chloride (704 mg, 7.11mmol) (I) and acetic anhydride (16.0g, 156mmol) by adding a toluene solution of (100 ml) 0 °C, 1 hours at the same temperature. The reaction mixture is poured into 2N hydrochloric acid aqueous solution, in toluene. The extract is washed with saturated salt solution, and dried in an anhydrous sodium sulfate, a vacuum concentrator. Concentrated silica gel column chromatography (elution solvent: ethyl acetate/n-hexane = 1/10) by, for compd. yellow oilies (yield 21.0g, yield 85percent) is obtained.
Reference: [1] Patent: JP2016/84346, 2016, A, . Location in patent: Paragraph 0056
[2] Patent: JP2016/84328, 2016, A, . Location in patent: Paragraph 0191
  • 18
  • [ 138526-69-9 ]
  • [ 220141-73-1 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5 h;
Stage #2: With acetic anhydride; copper(l) chloride In tetrahydrofuran; toluene at 0℃; for 1 h;
Method for producing 3 ', 4', 5'-trifluoroacetophenoneIodine (361 mg, 1.42 mmol) was added to a tetrahydrofuran solution (100 ml) of magnesium (3.53 g, 145 mmol)After adding 3,4,5-trifluorobromobenzene (30.0 g, 142 mmol)Was slowly added dropwise at room temperature. After stirring at the same temperature for 30 minutes, this solution was added to a toluene solution (100 ml) of copper (I) chloride (704 mg, 7.11 mmol) and acetic anhydride (16.0 g, 156 mmol)At 0 ° C., and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into 2 N aqueous hydrochloric acid solution,And extracted with toluene. The extract was washed with saturated brine,After drying over anhydrous sodium sulfate, it was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/10),The title compound as a yellow oil (yield 21.0 g, yield 85percent)Was obtained. 1 H NMR spectrum (CDCl3) .sigma .: 7.62-7.58 (2H, m), 2.58(3H, s).Production method of 3 ', 4', 5'-trifluoroacetophenone Magnesium
Reference: [1] Patent: JP2016/84347, 2016, A, . Location in patent: Paragraph 0144
  • 19
  • [ 15163-59-4 ]
  • [ 138526-69-9 ]
  • [ 915416-45-4 ]
YieldReaction ConditionsOperation in experiment
97% at 190℃; for 22 h; Inert atmosphere General procedure: To a dry 250 ml three-necked flask equipped with a magnetic stirrer was added 12.42 g (0.06 mol)Potassium o-nitrobenzoate, 0.22 g (0.0012 mol) cuprous iodide,0.12 g (0.0004 mol) of palladium acetylacetonate [Pd(acac)2],0.36 g (0.0014 mol) of triphenylphosphine (PPh3), 0.36 g (0.002 mol) of 1,10-phenanthroline,10.77 g (0.05 mol) of 3,4,5-trifluorobromobenzene (98.5percent by mass) and 80 g of anhydrous polyethylene glycol PEG-400, followed by vacuum displacement under nitrogen three times, stirring under nitrogen, stirring Warm up to 190°C,The reaction was 22 hours. The reaction was completed by gas chromatography or high pressure liquid chromatography.The reaction solution was cooled to room temperature, filtered, and 120 ml of water was added to the filtrate for uniform dilution.Extract three times with toluene (60 ml/time) and combine the extracts and wash twice with water (100 ml/sec).The organic phase was concentrated on a rotary evaporator and the resulting oily mixture was recrystallized from petroleum ether.After filtration, 10.81 g of yellow 3',4',5'-trifluoro-2-aminobiphenyl was obtained.Yield 96percent, purity 99percent.
Reference: [1] Patent: CN107488113, 2017, A, . Location in patent: Paragraph 0086; 0087; 0089; 0090; 0093
  • 20
  • [ 138526-69-9 ]
  • [ 915416-45-4 ]
Reference: [1] Patent: US2011/301356, 2011, A1,
[2] Patent: US2011/301356, 2011, A1,
[3] Patent: US2011/301356, 2011, A1,
[4] Patent: CN108276294, 2018, A,
  • 21
  • [ 61676-62-8 ]
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  • [ 827614-70-0 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 1, p. 263 - 271
  • 22
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  • [ 827614-70-0 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 2, p. 166 - 169
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