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[ CAS No. 53312-76-8 ]

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Chemical Structure| 53312-76-8
Chemical Structure| 53312-76-8
Structure of 53312-76-8 * Storage: {[proInfo.prStorage]}

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Product Details of [ 53312-76-8 ]

CAS No. :53312-76-8 MDL No. :MFCD15527336
Formula : C7H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :152.58 g/mol Pubchem ID :53417324
Synonyms :

Safety of [ 53312-76-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53312-76-8 ]

  • Downstream synthetic route of [ 53312-76-8 ]

[ 53312-76-8 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 53312-76-8 ]
  • [ 73936-80-8 ]
  • C30H34ClN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% 5.0 g (32.7 mmol) of <strong>[53312-76-8]3-aminochlorobenzonitrile</strong> are stirred, in portions, into 60 ml of water at 95 C. 30 ml of 32 % hydrochloric acid are then added dropwise, and the mixture is cooled to room temperature and stirred for 16 hours to complete the reaction. After cooling to from -10 to -15 C., 9.0 ml of a 4N solution of sodium nitrite in water are metered in in the course of 40 minutes. The resulting diazonium salt solution is stirred for 30 minutes at -10 C. 2.2 g (54 mmol) of sodium hydroxide beads are dissolved, with stirring, in a solution of 5 g (0.54 mmol) of 4-(1,1,3,3 tetramethylbutyl)-2-cumyl-phenol (95 % purity) in 70 ml of methanol and 10 ml of xylene. After the solution has been cooled to <-15 C., the diazonium salt solution is added dropwise thereto within a period of 100 minutes at from -15 to -5 C. During the addition an alkaline pH is maintained by metering in approximately 30 ml of 30 % sodium hydroxide solution in parallel. When the addition is complete, 50 ml of xylene are added. The red suspension is gradually brought to 25 C. and stirred overnight to complete the reaction. After the introduction of 150 ml of ethyl acetate with stirring, and the addition of 100 ml of water and 5 ml of acetic acid, the aqueous phase is separated off and the organic phase is washed three times with 100 ml of water each time. The organic phases are combined and concentrated using a vacuum rotary evaporator. Crystallisation of the residue from methanol yields 9.4 g (59 %) of 4-chloro-3-[2-hydroxy-3-(1-methyl-1-phenyl-ethyl)-5-(1,1,3,3-tetramethyl-butyl)-phenylazo]-benzonitrile (compound 216, Table 2). M.p. 190-191 C
  • 2
  • [ 34662-24-3 ]
  • [ 53312-76-8 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate In ethanol at 70℃; for 1.66667h; chemoselective reaction;
  • 3
  • [ 53312-76-8 ]
  • C7H4BrClN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With N-Bromosuccinimide In N,N-dimethyl-formamide at -10 - 20℃; for 1.66667h; 122.a A solution of the 3-amino-2-chloro-benzonitrile (1 g, 6.58 mmol) in DMF (20 mL) was cooled to -10 °C and NBS (1.17 g, 6.58 mmol, 1.0 equiv.) in DMF (10 mL) was added dropwise over 10 min. The mixture was stirred at -10 °C for 10 min. then the cooling batch was removed, and reaction was stirred at room temperature for 1.5h. Diluted with 10% Na2S2O3 (100 mL) and extracted with EtOAc (3 x 100 mL). Combined organics were washed with brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hex → 30 % EtOAc in hexanes) to afford the product (0.92 g, 60 %).
60% With N-Bromosuccinimide In N,N-dimethyl-formamide at -10 - 20℃; for 1.66667h; 122.a A solution of the 3-amino-2-chloro-benzonitrile (1 g, 6.58 mmol) in DMF (20 mL) was cooled to -10 °C and NBS (1.17 g, 6.58 mmol, 1.0 equiv.) in DMF (10 mL) was added dropwise over 10 min. The mixture was stirred at -10 °C for 10 min. then the cooling batch was removed, and reaction was stirred at room temperature for 1.5h. Diluted with 10% Na2S2O3 (100 mL) and extracted with EtOAc (3 x 100 mL). Combined organics were washed with brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hex → 30 % EtOAc in hexanes) to afford the product (0.92 g, 60 %).
  • 4
  • [ 53312-76-8 ]
  • C8H5BrClNS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1.67 h / -10 - 20 °C 2: tert.-butylnitrite / acetonitrile / 1.25 h / 20 - 60 °C
  • 5
  • [ 53312-76-8 ]
  • C24H27ClFN3OSSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1.67 h / -10 - 20 °C 2: tert.-butylnitrite / acetonitrile / 1.25 h / 20 - 60 °C 3: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 15 h / 100 °C
  • 6
  • [ 53312-76-8 ]
  • C24H27ClFN3O3SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1.67 h / -10 - 20 °C 2: tert.-butylnitrite / acetonitrile / 1.25 h / 20 - 60 °C 3: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 15 h / 100 °C 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
  • 7
  • [ 53312-76-8 ]
  • C18H13ClFN3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1.67 h / -10 - 20 °C 2: tert.-butylnitrite / acetonitrile / 1.25 h / 20 - 60 °C 3: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 15 h / 100 °C 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C
  • 8
  • [ 53312-76-8 ]
  • 1-(3-chloro-2-cyano-4-methylsulfonylphenyl)-4,6-difluoro-3,4-dihydro-2H-quinoline-8-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1.67 h / -10 - 20 °C 2: tert.-butylnitrite / acetonitrile / 1.25 h / 20 - 60 °C 3: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 15 h / 100 °C 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C 6: diethylamino-sulfur trifluoride / dichloromethane / 0.67 h / -10 - 20 °C
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