[ CAS No. 20925-27-3 ]

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2D
Chemical Structure| 20925-27-3
Chemical Structure| 20925-27-3
Structure of 20925-27-3

Quality Control of [ 20925-27-3 ]

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Related Doc. of [ 20925-27-3 ]

SDS

Product Details of [ 20925-27-3 ]

CAS No. :20925-27-3MDL No. :MFCD00035926
Formula :C7H5ClN2Boiling Point :339.5°C at 760 mmHg
Linear Structure Formula :C6H3ClCN2H2InChI Key :-
M.W :152.58Pubchem ID :88728
Synonyms :

Computed Properties of [ 20925-27-3 ]

TPSA : 49.8 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 20925-27-3 ]

Signal Word:WarningClass
Precautionary Statements:P280UN#:
Hazard Statements:H317Packing Group:
GHS Pictogram:

Application In Synthesis of [ 20925-27-3 ]

  • Upstream synthesis route of [ 20925-27-3 ]
  • Downstream synthetic route of [ 20925-27-3 ]

[ 20925-27-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 28163-00-0 ]
  • [ 20925-27-3 ]
YieldReaction ConditionsOperation in experiment
78% With hydrazine hydrate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate Step 4
A portion of 2-chloro-4-nitrobenzonitrile (5 g, 0.027 m) was heated with hydrazine monohydrate (110 ml) until the reaction began.
Another portion of 2-chloro-4-nitrobenzonitrile (35 g, 0.192 m) was added in predetermined amounts.
Once the evolution of nitrogen gas ceased, the reaction mixture was refluxed approximately thirty minutes, and then poured into stirred ice water.
The precipitate was filtered and the solid was crystallized from water to yield 2-chloro-4-aminobenzonitrile (25 g, 78percent, mp 117° C.).
Reference: [1] Patent: US4424371, 1984, A
  • 2
  • [ 21402-26-6 ]
  • [ 20925-27-3 ]
YieldReaction ConditionsOperation in experiment
60% at 145℃; Inert atmosphere General procedure: A mixture of compound 3a or 3b (19 mmol) and CuCN (29 mmol, 1.5 eq) in DMF (20 ml) was heated at 145 °C under nitrogen overnight. The reaction mixture was cooled to room temperature and then poured into ice water (50 ml). Ethyl acetate (100 ml) was added and the insoluble solid was filtered off (washed with ethyl acetate [2 x 30 ml]). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2 x 50 ml). The combined extracts were washed with saturated aqueous NaHCO3 solution (1 x 150 ml), brine (3 x 100 ml) and dried over Na2SO4. The resulting material was concentrated and the residue was purified by silica gel chromatography (petroleum ether:ethyl acetate, 10:1) to afford the title compound (4a or 4b) as a gray solid (60–65 percent yield).
Reference: [1] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 539 - 552
  • 3
  • [ 154607-01-9 ]
  • [ 20925-27-3 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 26, p. 4689 - 4692
  • 4
  • [ 873-74-5 ]
  • [ 21803-75-8 ]
  • [ 20925-27-3 ]
YieldReaction ConditionsOperation in experiment
95% With N-chloro-succinimide In dichloromethane; acetonitrile 3-chloro-4-cyanoaniline.
PREPARATION 2
(2-chloro-4-cyanoaniline)
To a stirred, 60° C. solution of 4-cyanoaniline (20 g, 0.169 mol) in acetonitrile (200 mL) was added slowly N-chlorosuccinimide (24.8 g, 0.186 mol) to keep the reaction at reflux.
After the addition of the N-chlorosuccinimide was complete, the reaction mixture was stirred at 60° C. for two hours.
The solvent was then removed under reduced pressure.
The residue was then dissolved in dichloromethane, washed with a 5percent sodium hydroxide solution, dried (Na2 SO4) and evaporated under reduced pressure to afford 24.5 g (95percent) of the title compound, 2-chloro-4-cyanoaniline, as a tan solid; m.p. 93°-95° C.
Reference: [1] Patent: US5034410, 1991, A
  • 5
  • [ 108-42-9 ]
  • [ 20925-27-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
[2] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 539 - 552
  • 6
  • [ 588-07-8 ]
  • [ 20925-27-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
  • 7
  • [ 22459-81-0 ]
  • [ 20925-27-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
  • 8
  • [ 22304-33-2 ]
  • [ 20925-27-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
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