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Chemical Structure| 13296-94-1
Chemical Structure| 13296-94-1
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Product Details of [ 13296-94-1 ]

CAS No. :13296-94-1 MDL No. :MFCD00025152
Formula : C6H5BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CGPPWNTVTNCHDO-UHFFFAOYSA-N
M.W : 217.02 Pubchem ID :25840
Synonyms :

Calculated chemistry of [ 13296-94-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.37
TPSA : 71.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 2.25
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : -0.33
Consensus Log Po/w : 1.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.249 mg/ml ; 0.00115 mol/l
Class : Soluble
Log S (Ali) : -3.39
Solubility : 0.0875 mg/ml ; 0.000403 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.28
Solubility : 1.14 mg/ml ; 0.00527 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 13296-94-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13296-94-1 ]

* 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 [ 13296-94-1 ]
  • Downstream synthetic route of [ 13296-94-1 ]

[ 13296-94-1 ] Synthesis Path-Upstream   1~27

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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1896, vol. <2> 53, p. 198
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  • [ 140-89-6 ]
  • [ 4845-58-3 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 3, p. 369 - 376
  • 3
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  • [ 5411-50-7 ]
Reference: [1] Journal of the Chemical Society, 1951, p. 1774,1778
  • 4
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  • [ 16588-26-4 ]
Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1913, vol. <5> 22 I, p. 823[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1914, vol. <5> 23 I, p. 283 Anm.
  • 5
  • [ 615-36-1 ]
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Reference: [1] Synthesis, 1989, # 10, p. 761 - 763
  • 6
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  • [ 99-29-6 ]
Reference: [1] Synthetic Communications, 2012, vol. 42, # 24, p. 3655 - 3663,9
[2] Journal of the Chemical Society, 1902, vol. 81, p. 494
  • 7
  • [ 100-01-6 ]
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YieldReaction ConditionsOperation in experiment
99% With pyrrolidone hydrotribromide In methanol; dichloromethane at 20℃; for 0.5 h; At room temperature a solution of 4-nitroaniline (1.60 g, 11.6mmol, 1 equiv.) in DCM (40 mL) and MeOH (20 mL) was treated with PHT (6.30 g, 12.7mmol, 1.1 equiv.) in a portion-wise manner. Stirring was then continued for 0.5 h. The mixture was diluted with Et2O (50 mL) and washed first with a saturated aqueous solution of Na2S2O3 (40 mL) and then brine (40 mL). The organic extract was dried over MgSO4 before filtration and solvent removal under reduced pressure. Purification by flash columnchromatography (c-Hex-EtOAc; 2:1) gave S8 (2.50 g, 99percent) as a yellow solid.
92% With 1,2-ethanediylbis(triphenylphosphonium) ditribromide In methanol; dichloromethane at 20℃; for 0.0833333 h; General procedure: To a mixture of anilines or phenols (0.7 mmol) the brominatingagent (1) (0.72 g, 0.7 mmol) in dichloromethane(30 ml)-methanol (15 ml) was added. The reactionmixture was stirred at room temperature until decolorizationof the orange solution took place. The progress of thereaction was monitored by TLC (eluent: n-hexane/ethylacetate, 7:3). After completion of the reaction, the solventwas evaporated and diethyl ether (10 ml) was added to theresidue. The supernatant was decanted and the insolubleresidue was washed by ether (3 × 10 ml). The combinedether extracts were dried on magnesium sulfate and also evaporated under vacuum to afford monobromo anilines ormonobromo phenols which was purified by flash columnchromatography over silica gel (n-hexane/ethyl acetate,7:3).
92% With acetic acid; potassium bromide In water at 30℃; for 1 h; 276 mg (2 mmol) of p-nitroaniline and 143 mg (1.2 mmol) of potassium bromide were added to a 50 ml three-necked flask Add AcOH: H2O = 9: 1 10ml solvent, transferred to constant temperature magnetic stirring water bath, control the temperature of 30 stirring anti- 1.8 g (1.8 mmol) of ZnAl-BrO3 - LDHs were added slowly in portions over a period of 1 hour before the reaction. After the reaction, The reaction solution was extracted with methylene chloride and the combined organic phases were added to a dichloromethane phase by adding two syrups of silica gel (200-300), And the dichloromethane was distilled off under reduced pressure, and the residue was purified by column chromatography (petroleum ether: ethyl acetate = 10: 1 as eluent)Separation gave 399 mg of pure product. The material was a yellow solid in 92percent yield.
91% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 18.5 h; Darkness A solution of 4-nitroaniline (10 g, 72 mmol) in DMF (150 mL) as added NBS (12.9 g, 72 mmol) portionwise and the mixture was stirred for 30 min at the same temperature. Then the ice-bath was removed and the stirring was continued at rt overnight (18 h). The mixture was poured into water (500 mL) and filtered, the orange solid was washed with water (50 mL × 2) and recrystallized from EtOH to affordpale-yellow crystals (14.3 g, 92 percent); Rf = 0.21 (PE : EtOAc = 5 : 1); m.p. 98 -100 °C; 1H-NMR (CDCl3, 300 MHz) δ: 8.37 (d, J = 2.1 Hz, 1H), 8.03 (dd, J = 2.4 Hz, J = 2.7 Hz, 1H), 6.74 (d, J = 9.0 Hz, 1H), 4.48 (br, 2H).
85% With o-xylylene bis(triethylammonium tribromide) In acetonitrile at 20℃; for 0.116667 h; General procedure: To a magnetic solution of aromatic compound (1 mmol)in acetonitrile (5 mL), OXBTEATB (0.233 g, 0.5 mmol) wasadded and stirred at room temperature for the appropriatetime (Table 1). The reaction was monitored by TLC (eluent:n-hexane/ethyl acetate: 5/1). The reaction mixture was transferredinto a separatory funnel after filtration of OXBTEABand was extracted with water (15 mL) and dichloromethane(20 mL). The organic layer was dried over anhydrousNa2SO4, and the solvent was concentrated in a rotary evaporator.The crude product was purified by passing it over acolumn of silica gel using a mixture of n-hexane and ethylacetate as the eluent. In order to regenerate the reagent, whitesolid was treated with liquid bromine. All the product structureswere confirmed by comparison of melting point or 1HNMR spectra with ones reported in the literature [29a-29e].
83% at 90℃; for 10 h; Green chemistry General procedure: To a round bottom flask was added 5 mmol of acetophenone, 0.5 mmol of 2-methylpyridine nitrate and 5.5 mmol of 40 wtpercent HBr, 60 ° C under the open flask stir reaction 6h, The yield of α-bromoacetophenone was 95percent The product was isolated by silica gel column chromatography (ethyl acetate / boiling point 60-90 ° C petroleum ether) at 200-300 mesh, The isolated yield was 88percent.
80% With bromine In acetic acid at 20℃; for 2 h; Bromine (2.05 mL, 40 mmol) was added dropwise to a solution of 4-nitroaniline(5.0 g, 36 mmol) in acetic acid (150 mL) at room temperature under an inert atmosphere of argon. The resulting reaction mixture was stirred at room temperature for 2 h. It was then quenched with dilute aqueous Na2S2O3 (150 mL) and extracted with EtOAc (2 x 500 mL).The combined organic layers were added carefully to a saturated aqueous solution ofNaHCO3 (1 L) and stirred at room temperature for 30 min until all gas evolution had ceased. The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (3:1 petroleum ether/CH2Cl2) to afford 2-bromo-4-nitroaniline as a yellow solid (6.3 g, yield: 80percent).1HNMR (400MHz, CDC13) δ: 8.39 (IH, d, J=2.4 Hz), 8.06 (IH, d, J= 2.4 Hz), 6.77 (IH, d,J= 9.2 Hz).
80%
Stage #1: at 20℃; for 2 h;
Stage #3: With water; sodium hydrogencarbonate In ethyl acetate at 20℃; for 0.5 h;
Preparation of 2-bromo-4-nitroaniline:Bromine (2.05 mL, 40 mmol) was added dropwise to a solution of 4- nitroaniline (5.0 g, 36 mmol) in acetic acid (150 mL) at rt under an inert atmosphere of argon. The resulting reaction mixture was stirred at room temperature for 2 h. It was then quenched with dilute aqueous Na2S2O3 (150 mL) and extracted with <n="84"/>EtOAc (2 x 500 mL). The combined organic layers were added carefully to a saturated aqueous solution OfNaHCO3 (1 L) and stirred at room temperature for 30 min until all gas evolution had ceased. The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (3 : 1 petroleum ether/CH2Cl2) to afford 2-bromo-4- nitroaniline as a yellow solid (6.3 g, yield: 80percent). 1HNMR (400MHz, CDC13) δ: 8.39 (IH, d, J=2.4 Hz), 8.06 (IH, d, J= 2.4 Hz), 6.77 (IH, d, J= 9.2 Hz).
80% With bromine In acetic acid 2-Bromo-4-nitroaniline
To a solution of 4-nitro-aniline (25 g, 0.18 mol) in HOAc (150 mL) was added liquid Br2 (30 g, 0.19 mol) dropwise at room temperature.
The mixture was stirred for 2 hours.
The solid was collected by filtration and poured into water (100 mL), which was basified with sat. aq.
NaHCO3 to pH 7 and extracted with EtOAc (300 mL*3).
The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give 2-bromo-4-nitroaniline (30 g, 80percent), which was directly used in the next step.
80% for 2 h; To a solution of 4-nitro-phenylamine (50 g, 0.36 mol) in AcOH (500 mL) was added Br2 (60 g, 0.38 mol) dropwise at 5° C.
The mixture was stirred for 30 min at that temperature.
The insoluble solid was collected by filtration and basified with saturated aqueous NaHCO3 to pH 7.
The aqueous phase was extracted with EtOAc (300 mL*3).
The combined organic layers were dried and evaporated under reduced pressure to obtain compound 2-bromo-4-nitroaniline (56 g, 72percent), which was directly used in the next step.
72%
Stage #1: at 5 - 20℃; for 0.5 - 2 h;
Stage #2: With sodium hydrogencarbonate In water
Example 33 2-Cyclopropyl-1H-indol-5-amine 2-Bromo-4-nitroaniline To a solution of 4-nitro-aniline (25 g, 0.18 mol) in HOAc (150 mL) was added liquid Br2 (30 g, 0.19 mol) dropwise at room temperature. The mixture was stirred for 2 hours. The solid was collected by filtration and poured into water (100 mL), which was basified with sat. aq. NaHCO3 to pH 7 and extracted with EtOAc (300 mL.x.3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give 2-bromo-4-nitroaniline (30 g, 80percent), which was directly used in the next step.; Example 35 2-Phenyl-1H-indol-5-amine 2-Bromo-4-nitroaniline To a solution of 4-nitroaniline (50 g, 0.36 mol) in AcOH (500 mL) was added liquid Br2 (60 g, 0.38 mol) dropwise at 5° C. The mixture was stirred for 30 min at that temperature. The insoluble solid was collected by filtration and poured into EtOAc (200 mL). The mixture was basified with saturated aqueous NaHCO3 to pH 7. The organic layer was separated. The aqueous phase was extracted with EtOAc (300 mL.x.3). The combined organic layers were dried and evaporated under reduced pressure to give 2-bromo-4-nitroaniline (56 g, 72percent), which was directly used in the next step.; 2-Bromo-4-nitroaniline To a solution of 4-nitro-phenylamine (50 g, 0.36 mol) in AcOH (500 mL) was added Br2 (60 g, 0.38 mol) dropwise at 5° C. The mixture was stirred for 30 min at that temperature. The insoluble solid was collected by filtration and basified with saturated aqueous NaHCO3 to pH 7. The aqueous phase was extracted with EtOAc (300 mL.x.3). The combined organic layers were dried and evaporated under reduced pressure to obtain compound 2-bromo-4-nitroaniline (56 g, 72percent), which was directly used in the next step.
72% With bromine In acetic acid 2-Bromo-4-nitroaniline
To a solution of 4-nitroaniline (50 g, 0.36 mol) in AcOH (500 mL) was added liquid Br2 (60 g, 0.38 mol) dropwise at 5° C.
The mixture was stirred for 30 min at that temperature.
The insoluble solid was collected by filtration and poured into EtOAc (200 mL).
The mixture was basified with saturated aqueous NaHCO3 to pH 7.
The organic layer was separated.
The aqueous phase was extracted with EtOAc (300 mL*3).
The combined organic layers were dried and evaporated under reduced pressure to give 2-bromo-4-nitroaniline (56 g, 72percent), which was directly used in the next step.

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YieldReaction ConditionsOperation in experiment
65.6% With bromine In water; acetic acid EXAMPLE I
2-bromo-4-nitroaniline
100 g (0.724 mol) of p-nitroaniline was slowly added to 1550 ml of glacial acetic acid at 40° C.
After cooling the solution to 20° C., 37.4 ml (116.65 g, 0.730 mol) of bromine was added dropwise over a period of one h, after which the solution was allowed to stir an additional 45 min. at 20° C.
The precipitate which formed during the reaction was collected by suction filtration and stirred with 2500 ml of 10percent aqueous sodium bisulfite for 16 h; collected again by suction filtration and washed with 2500 ml of water.
The solid was air-dried for 24 h.
The crude material (139 g) was recrystallized twice from 65percent methanol to yield 103 g (65.6percent) of a yellow crystalline solid which melted at 101°-102° C.; IR (KBr) 3500, 3400, 1125 cm-1 (NH2); 1500, 1325 (NO2).
Anal. Calcd. for C6 H5 N2 O2 Br: C,33.18; H, 2.30; N, 12.90. Found: C, 33.26; H, 2.28; N, 12.92.
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[3] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 88,89
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  • [ 7149-14-6 ]
YieldReaction ConditionsOperation in experiment
77% With potassium iodide; sodium nitrite In water; acetonitrile at 0 - 5℃; for 0.5 h; Ice-cold solution of sodium nitrite (57.2 g, 829 mmol) and potassium iodide (138 g, 829 mmol) in water (25 mL) was added drop wise simultaneously to a stirred suspension of 2-bromo-4-nitroaniline (60 g, 276 mmol) in acetonitrile (250 mL) at 0-5 °C and stirred for 30 minutes. The reaction mixture was then poured on to ice-cold water (1000 mL). The solid obtained was filtered, washed with water and dried to afford the titlecompound.Yield: 70.0 g (77 percent); 1H NMR (300 MHz, CDCI3): O 7.86 (dd, 1H, J= 8.7, 2.4 Hz, Ar), 8.10(d, 1H, J= 8.7 Hz, Ar), 8.45 (d, 1H, J= 2.4 Hz, Ar); MS (El, 70 eV): m/z 328.3 (M+H).
Reference: [1] Patent: WO2015/49629, 2015, A1, . Location in patent: Page/Page column 102
[2] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[3] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
[4] Chemistry - A European Journal, 2017, vol. 23, # 11, p. 2660 - 2665
  • 27
  • [ 13296-94-1 ]
  • [ 53312-82-6 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 2, p. 275 - 280
[2] Patent: WO2009/3077, 2008, A1,
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