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Chemical Structure| 2729-37-5 Chemical Structure| 2729-37-5

Structure of 2729-37-5

Chemical Structure| 2729-37-5

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Product Details of [ 2729-37-5 ]

CAS No. :2729-37-5
Formula : C6H4Cl2FN
M.W : 180.01
SMILES Code : NC1=CC(Cl)=C(F)C=C1Cl
MDL No. :MFCD06808808
InChI Key :PFVXJOLBILNOHG-UHFFFAOYSA-N
Pubchem ID :223090

Safety of [ 2729-37-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P264-P270-P301+P312-P330

Application In Synthesis of [ 2729-37-5 ]

* 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.

  • Downstream synthetic route of [ 2729-37-5 ]

[ 2729-37-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 2624-66-0 ]
  • [ 2729-37-5 ]
YieldReaction ConditionsOperation in experiment
89% With water; iron; ammonium chloride; In ethanol; at 80℃; A mixture of 1,4-dichloro-2-fluoro- 5-nitrobenzene (2.79 g, 13.29 mmol), iron powder (2.97 g, 53.1 mmol) and ammonium chloride (3.55 g, 66.4 mmol) in ethanol (60.4 mL) and water (6.04 mL) was heated at 80 C overnight. The reaction mixture was concentrated under vacuum to remove the volatiles. The residue was diluted with water (100 mL) and and extracted with DCM (150 mL). The extract was dried over MgSO4, filtered and concentrated under vacuum. The residue was purified with a silica gel flash column, eluting with 0-50% EtOAc in hexane to afford 2,5-dichloro-4-fluoroaniline (2.13 g, 11.83 mmol, 89 % yield) as a tan solid. MS (ESI) m/z: 179.9 [M+H]+; 1H NMR (500 MHz, chloroform-d δ 7.12 (d, J=8.25 Hz, 1H), 6.81 (d, J=6.88 Hz, 1H), 3.97 (br s, 2H).
  • 5
  • [ 367-21-5 ]
  • [ 2729-37-5 ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinamide; In tetrahydrofuran; at 20℃; Step-1 :-Preperation of 2,5-dichloro-4-fluoro-phenylamine:- To a solution of 3-chloro-4-fluoro-phenylamine (1.0 g, 6.89 mmol) in THF (15 mL) was added N-chloro succinamide (0.917 g, 6.89 mmol). The reaction mass was stirred at RT for 16-18 hours. THF was removed and water was added and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.700 g of desired product. .HNMR (DMSO- 6): δ 5.50 (s, 2H), 6.90 (d, J = 7.5 Hz, 1H), 7.41 (d, 7 = 9.3 Hz, 1H).
  • 6
  • [ 2729-37-5 ]
  • (2,5-dichloro-4-fluorophenyl)hydrazine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% To a solution of <strong>[2729-37-5]2,5-dichloro-4-fluoroaniline</strong> (2.13 g, 11.83 mmol) in acetic acid (6 mL, 105 mmol) at rt was added conc. hydrochloric acid (12.0 mL, 395 mmol). To the resulting suspension at -10 to -5 oC was added a solution of sodium nitrite (0.980 g, 14.20 mmol) in water (3.5 mL) over 10 min. The mixture was stirred at -10 to -5 oC for 60 min before a solution of tin(II) chloride dihydrate (5.87 g, 26.0 mmol) in conc. hydrochloric acid (12.0 mL, 395 mmol), pre-cooled at 0 oC, was added dropwise over 10 min. The mixture was stirred at -10 to -5 oC for 1 h and then at -5 to 0 oC for 1 h. The precipitating product, (2,5-dichloro-4-fluorophenyl)hydrazine, HCl (2.81 g, 11.78 mmol, 100 % yield), was collected as a pale solid by suction filtration and dried at 50 oC under vacuum. MS (ESI) m/z: 194.8 [M+H]+; 1H NMR (500 MHz, DMSO-d6) δ 10.24 (br s, 2H), 8.23 (br s, 1H), 7.71 (d, J=8.80 Hz, 1H), 7.38 (d, J=6.88 Hz, 1H).
 

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