Home Cart 0 Sign in  

[ CAS No. 56136-82-4 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 56136-82-4
Chemical Structure| 56136-82-4
Structure of 56136-82-4 * Storage: {[proInfo.prStorage]}

Quality Control of [ 56136-82-4 ]

Related Doc. of [ 56136-82-4 ]

SDS
Alternatived Products of [ 56136-82-4 ]
Alternatived Products of [ 56136-82-4 ]

Product Details of [ 56136-82-4 ]

CAS No. :56136-82-4 MDL No. :MFCD00768959
Formula : C8H9BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :245.07 g/mol Pubchem ID :-
Synonyms :

Safety of [ 56136-82-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330-P501 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 56136-82-4 ]

  • Downstream synthetic route of [ 56136-82-4 ]

[ 56136-82-4 ] Synthesis Path-Downstream   1~14

  • 2
  • [ 3460-18-2 ]
  • [ 109-89-7 ]
  • [ 56136-82-4 ]
YieldReaction ConditionsOperation in experiment
93% In water at 105℃; for 24h;
  • 3
  • [ 56136-82-4 ]
  • [ 5720-07-0 ]
  • [ 1062191-99-4 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In tetrahydrofuran; water at 75℃; for 18h;
  • 4
  • [ 56136-82-4 ]
  • [ 1334474-36-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 24 h / Reflux 2: sodium dithionite / ethanol; water; N,N-dimethyl-formamide / 24 h / 80 °C / Reflux; Inert atmosphere
  • 5
  • [ 56136-82-4 ]
  • [ 1207190-79-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / Reflux 2: sodium dithionite / ethanol; water; N,N-dimethyl-formamide / 24 h / 80 °C / Reflux; Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / 1,4-dioxane; ethanol / 24.3 h / 20 °C / Inert atmosphere; Reflux
  • 6
  • [ 56136-82-4 ]
  • [ 1334474-38-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / Reflux 2: sodium dithionite / ethanol; water; N,N-dimethyl-formamide / 24 h / 80 °C / Reflux; Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / 1,4-dioxane; ethanol / 24.3 h / 20 °C / Inert atmosphere; Reflux
  • 7
  • [ 56136-82-4 ]
  • [ 1334474-39-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / Reflux 2: sodium dithionite / ethanol; water; N,N-dimethyl-formamide / 24 h / 80 °C / Reflux; Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / 1,4-dioxane; ethanol / 24.3 h / 20 °C / Inert atmosphere; Reflux
  • 8
  • [ 364-73-8 ]
  • [ 75-04-7 ]
  • [ 56136-82-4 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine In tetrahydrofuran; acetonitrile at 85℃; for 16h; 170.1 Step 1:
(4-Bromo-2-nitro-phenyl)-ethyl-amine (170a)
Ethylamine (2M in THF, 1.37 mL, 2.7 mmol) and 5-bromo-2-fluoronitrobenzene (500 mg, 2.3 mmol) was added in a solution of acetonitrile (3 mL) and triethylamine (315 μL, 2.7 mmol). The mixture was stirred at 85°C for 16 hours. Water was added and the organic layer was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated to give compound (170a) as orange powder (550 mg, 2.2 mmol, 98%). MS m/z ([M+H]+) 246.
98% In ethanol at 50℃; for 4h; Sealed tube; 22.1 Example 22: (E)-3-(1-ethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-N-(3-fluoro-2- methylphenyl)acrylamide Step 1: Into a 100-mL sealed tube, was placed 4-bromo-1-fluoro-2-nitrobenzene (2.0 g, 9.09 mmol, 1.0 eq), EtOH (8.0 mL, 1.0 eq), ethylamine (22.73 mL, 45.45 mmol, 5.0 eq, 2 M in ethanol). The resulting solution was stirred for 4 h at 50 °C. The resulting mixture was concentrated. The residue was diluted with 15 mL of H2O and stirred 15 min. The solids were collected by filtration. This resulted in 2.2 g (98%) of 4-bromo-N-ethyl-2-nitroaniline as a red solid. LC-MS (ES, m/z): [M+H]+=245
98% In ethanol at 50℃; for 4h; Sealed tube; 22.1 Example 22: (E)-3-(1-ethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-N-(3-fluoro-2- methylphenyl)acrylamide Step 1: Into a 100-mL sealed tube, was placed 4-bromo-1-fluoro-2-nitrobenzene (2.0 g, 9.09 mmol, 1.0 eq), EtOH (8.0 mL, 1.0 eq), ethylamine (22.73 mL, 45.45 mmol, 5.0 eq, 2 M in ethanol). The resulting solution was stirred for 4 h at 50 °C. The resulting mixture was concentrated. The residue was diluted with 15 mL of H2O and stirred 15 min. The solids were collected by filtration. This resulted in 2.2 g (98%) of 4-bromo-N-ethyl-2-nitroaniline as a red solid. LC-MS (ES, m/z): [M+H]+=245
71% In ethanol at 20℃; for 24h;

  • 9
  • [ 364-73-8 ]
  • [ 557-66-4 ]
  • [ 56136-82-4 ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine at 80℃; for 16h; 3.1 Step 1: 4-bromo-N-ethyl-2-nitroaniline A solution of 4-bromo-1-fluoro-2-nitrobenzene (5.00 g, 22.73 mmol) and ethylamine hydrochloride (9.27 g, 113.64 mmol) in Et3N (13.80 g, 136.38 mmol) was stirred for 16 h at 80 oC. The resulting mixture was concentrated under reduced pressure. The residue was quenched with sat. NH4HCO3 (aq.) at room temperature. The resulting mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to afford 4-bromo-N-ethyl- 2-nitroaniline (5 g, 89%) as a red solid which was used in the next step without further purification. MS ESI calculated for C8H9BrN2O2 [M + H]+, 244.98, 246.98, found 245.05, 247.05.
89% With triethylamine at 80℃; for 16h; 3.1 Step 1: 4-bromo-N-ethyl-2-nitroaniline A solution of 4-bromo-1-fluoro-2-nitrobenzene (5.00 g, 22.73 mmol) and ethylamine hydrochloride (9.27 g, 113.64 mmol) in Et3N (13.80 g, 136.38 mmol) was stirred for 16 h at 80 oC. The resulting mixture was concentrated under reduced pressure. The residue was quenched with sat. NH4HCO3 (aq.) at room temperature. The resulting mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to afford 4-bromo-N-ethyl- 2-nitroaniline (5 g, 89%) as a red solid which was used in the next step without further purification. MS ESI calculated for C8H9BrN2O2 [M + H]+, 244.98, 246.98, found 245.05, 247.05.
33% With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide for 1.25h; Inert atmosphere;
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 80℃; for 12h; 45.A 4-bromo-N-ethyl-2-nitroaniline A solution of 4-bromo-l-fluoro-2-nitrobenzene (0.560 ml, 4.55 mmol), ethanamine, HC1 (0.371 g, 4.55 mmol) and DIEA (1.588 ml, 9.09 mmol) in DMA (5.05 ml) was heated to 80 °C for 12 h. The reaction mixture was cooled to room temperature, diluted with water (5 mL) and extracted with EtOAc (3x10 mL). The combined organics were washed with brine (1x10 mL), dried (MgS04), filtered and concentrated under reduced pressure. The crude material was carried on without further purification. Obtained 4-bromo-N-ethyl-2-nitroaniline (1115 mg, 4.55 mmol, 95% crude yield). LC/MS (ESI) m/e 245.0, 247.0 Br pattern [(M+H)+, calcd for C8H10BrN2O2 245.0].
With triethylamine In tetrahydrofuran; acetonitrile at 80℃; for 2h; S59.1 Step 1. Synthesis of 4-bromo-N-ethyl-2-nitroaniline To a solution of 4-bromo-1-fluoro-2-nitrobenzene (5.0 g, 22.73 mmol) in ACN/THF (50.0 mL/50.0 mL) was added TEA (13.8 g, 136.37 mmol) and ethanamine hydrochloride (9.3 g, 113.64 mmol) at room temperature. The resulting mixture was stirred at 80 °C for 2 h. After the reaction was completed, the resulting mixture was diluted with H2O and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to afford 4-bromo-N- ethyl-2-nitroaniline (5.5 g, crude) as an orange solid. LCMS (ESI, m/z): [M+H]+ =245.0.

  • 10
  • [ 56136-82-4 ]
  • 4-bromo-N1-ethylbenzene-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With iron(0); glacial acetic acid In ethanol at 70℃; for 16h; Inert atmosphere; 3.2 Step 2: 4-bromo-N1-ethylbenzene-1,2-diamine To a mixture of Fe (2.73 g, 48.96 mmol) in EtOH (66.00 mL) was added AcOH (3.30 mL, 54.90 mmol). The resulting mixture was stirred for 30 min at 70oC under nitrogen atmosphere. To the above mixture was added 4-bromo-N-ethyl-2-nitroaniline (3.00 g, 12.24 mmol). The reaction mixture was stirred for 16 h at 70oC. The resulting mixture was filtered, the filter cake was washed with THF. The filtrate was concentrated under reduced pressure. The residue was quenched by the addition of sat. NH4HCO3 (aq.) (50 mL) at room temperature. The resulting mixture was extracted with EtOAc (3 x 50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to afford 4-bromo-N1-ethylbenzene-1,2-diamine (2 g, 75%) as a brown solid which was used in next step without further purification. MS ESI calculated for C8H11BrN2 [M + H]+, 215.01, 217.01, found 215.10, 217.10.
75% With iron(0); glacial acetic acid In ethanol at 70℃; for 16h; Inert atmosphere; 3.2 Step 2: 4-bromo-N1-ethylbenzene-1,2-diamine To a mixture of Fe (2.73 g, 48.96 mmol) in EtOH (66.00 mL) was added AcOH (3.30 mL, 54.90 mmol). The resulting mixture was stirred for 30 min at 70oC under nitrogen atmosphere. To the above mixture was added 4-bromo-N-ethyl-2-nitroaniline (3.00 g, 12.24 mmol). The reaction mixture was stirred for 16 h at 70oC. The resulting mixture was filtered, the filter cake was washed with THF. The filtrate was concentrated under reduced pressure. The residue was quenched by the addition of sat. NH4HCO3 (aq.) (50 mL) at room temperature. The resulting mixture was extracted with EtOAc (3 x 50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to afford 4-bromo-N1-ethylbenzene-1,2-diamine (2 g, 75%) as a brown solid which was used in next step without further purification. MS ESI calculated for C8H11BrN2 [M + H]+, 215.01, 217.01, found 215.10, 217.10.
63% With ammonia hydrochloride; zinc powder In water monomer; acetone at 20℃; for 3h; 22.2 Step 2: Into a 50-mL round-bottom flask, was placed 4-bromo-N-ethyl-2-nitroaniline (2.0 g, 8.16 mmol, 1.0 eq), acetone (16.0 mL), H2O (2.0 mL), NH4Cl (4.37 g, 81.61 mmol, 10.0 eq), Zn (2.67 g, 40.80 mmol, 5.0 eq). The resulting solution was stirred for 3 h at room temperature. The solids were filtered out. The filtrate was concentrated. The residue was diluted with 20 mL of H2O and stirred 15 min. The solids were collected by filtration. This resulted in 1.1 g (63%) of 4- bromo-N1-ethylbenzene-1,2-diamine as a light yellow solid. LC-MS (ES, m/z): [M+H]+=215
63% With ammonia hydrochloride; zinc powder In water monomer; acetone at 20℃; for 3h; 22.2 Step 2: Into a 50-mL round-bottom flask, was placed 4-bromo-N-ethyl-2-nitroaniline (2.0 g, 8.16 mmol, 1.0 eq), acetone (16.0 mL), H2O (2.0 mL), NH4Cl (4.37 g, 81.61 mmol, 10.0 eq), Zn (2.67 g, 40.80 mmol, 5.0 eq). The resulting solution was stirred for 3 h at room temperature. The solids were filtered out. The filtrate was concentrated. The residue was diluted with 20 mL of H2O and stirred 15 min. The solids were collected by filtration. This resulted in 1.1 g (63%) of 4- bromo-N1-ethylbenzene-1,2-diamine as a light yellow solid. LC-MS (ES, m/z): [M+H]+=215
62% With sodium dihydrosulfite; anhydrous sodium carbonate In tetrahydrofuran; methanol; water monomer for 0.25h; Inert atmosphere;
With hydrogenchloride; tin(II) chloride dihydrochloride In water monomer at 50℃; for 1.5h; 45.B 4-bromo-N1-ethylbenzene- 1 ,2- diamine A solution of 4-bromo-N-ethyl-2-nitroaniline (1115 mg, 4.55 mmol) and tin(II) chloride dihydrate (6160 mg, 27.3 mmol) in hydrochloric acid, 37% (22.8 mL) was heated to 50 °C for 1.5h. The reaction mixture was cooled to 0 °C and quenched with 10N NaOH. The solution was extracted with ethyl acetate (3x15 mL). The combined organics were washed with brine (1x10 mL), dried (MgS04), filtered and concentrated under reduced pressure. Obtained 4-bromo- -ethylbenzene- 1 ,2- diamine (598 mg, 2.502 mmol, 55%> crude yield, 90%> purity) as an amorphous orange solid which was carried on without further purification. LC/MS (ESI) m/e 215.0, 217.0 [(M+H)+, calcd for C8H12BrN2 215.0]. bz

  • 11
  • [ 56136-82-4 ]
  • (R)-benzyl 1-(5-bromo-2-(ethylamino)phenylamino)-4-methyl-1-oxopentan-2-ylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tin(II) chloride dihdyrate; hydrogenchloride / water / 1.5 h / 50 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 14 h / 20 °C
  • 12
  • [ 56136-82-4 ]
  • (R)-benzyl 1-(5-bromo-1-ethyl-1H-benzo[d]imidazol-2-yl)-3-methylbutylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tin(II) chloride dihdyrate; hydrogenchloride / water / 1.5 h / 50 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 14 h / 20 °C 3: acetic acid / 1.5 h / 65 °C
  • 13
  • [ 56136-82-4 ]
  • (R)-benzyl 1-(1-ethyl-5-(pyridin-4-yl)-1H-benzo[d]imidazol-2-yl)-3-methylbutylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tin(II) chloride dihdyrate; hydrogenchloride / water / 1.5 h / 50 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 14 h / 20 °C 3: acetic acid / 1.5 h / 65 °C 4: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 5 h / Sealed tube; Inert atmosphere; Heating
  • 14
  • [ 56136-82-4 ]
  • (R)-1-(1-ethyl-5-(pyridin-4-yl)-1H-benzo[d]imidazol-2-yl)-3-methylbutan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tin(II) chloride dihdyrate; hydrogenchloride / water / 1.5 h / 50 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 14 h / 20 °C 3: acetic acid / 1.5 h / 65 °C 4: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 5 h / Sealed tube; Inert atmosphere; Heating 5: methoxybenzene; methanesulfonic acid / dichloromethane / 1.5 h / 20 °C
Historical Records