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Chemical Structure| 3964-52-1 Chemical Structure| 3964-52-1
Chemical Structure| 3964-52-1

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Product Details of 4-Amino-2-chlorophenol

CAS No. :3964-52-1
Formula : C6H6ClNO
M.W : 143.57
SMILES Code : C1=C(N)C=CC(=C1Cl)O
MDL No. :MFCD00128891
InChI Key :ZYZQSCWSPFLAFM-UHFFFAOYSA-N
Pubchem ID :77578

Safety of 4-Amino-2-chlorophenol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-Amino-2-chlorophenol

* 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 [ 3964-52-1 ]

[ 3964-52-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 5131-60-2 ]
  • [ 3964-52-1 ]
  • chloro-[1,4]benzoquinone-4-(2,4-diamino-5-chloro-phenylimine) [ No CAS ]
  • 2
  • [ 98556-31-1 ]
  • [ 3964-52-1 ]
  • [ 908332-08-1 ]
YieldReaction ConditionsOperation in experiment
94.5% To a stirred mixture of 4-Chloro-6-iodoquinazoline ( 10.0 g) and 4-Amino-2- chlorophenol (4.94 g) in Acetonitrile (100 ml) was refluxed for 1 hour. Reaction was monitored by TLC. On completion of reaction the reaction mixture was cooled to 20- 25C and the solid was filtered. Crude 2-chloro-4-(6-iodoquinazolin-4-ylamino)phenol hydrochloride so obtained was dissolved in demineralized water and neutralized with Sodium carbonate (3.65 g). Solid was filtered and dried under vacuum at 60-65C till constant weight. Weight: 13 g Yield: 94.5 % MS (ES+) m/z: 398 [M+H]+ & 400 [M+H+2]+ 1H NMR (400 MHz; DMSO-d6): 7.06 (d, J=8.8 Hz, 1H), 7.47 (d, J=8.8 Hz, 1H), 7.64 (d, J=8.8 Hz, 1H), 7.77 (s, 1H), 8.28 (d, J=8.8 Hz, 1H), 8.84 (s, 1H), 9.13 (s, 1H), 10.39 (s, 1H, OH), 1 1.06 (s, 1Η, ΝΗ).
  • 3
  • [ 68500-37-8 ]
  • [ 3964-52-1 ]
  • 2-chloro-4-((7-methoxyquinolin-4-yl)oxy)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% To a solution of 4-amino-2-chlorophenol (158 mg, 1.1 mmol) in DMSO (2 mL) was added NaH (88 mg, 2.2 mmol, 60percent in mineral oil) at rt. The reaction was stirred at rt for 15 minutes, followed by the addition of <strong>[68500-37-8]4-chloro-7-methoxyquinoline</strong> (194 mg, 1.0 mmol). The reaction was microwaved at 150 °C for 2 hours, then cooled to rt, quenched with water (10 mL) and extracted with EtOAc (30 mL). The organic phase was separated, washed with brine (30 mL x 3), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 1/1) to give the title compound as a pink solid (190 mg, 63percent). MS (ESI, pos. ion) m/z: 301.2 [M+H]+; FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO-i): delta 3.93 (s, 3H), 5.44 (s, 2H), 6.41 (d, J = 5.2 Hz, 1H), 6.91 (d, J = 8.7 Hz, 1H), 6.99 (m, 1H), 7.21 (d, J= 2.6 Hz, 1H ), 7.26 (m, 1H), 7.38(d, J = 2.6 Hz, 1H), 8.17(d, J= 8.7 Hz, 1H), 8.57(d, J= 5.2 Hz, 1H).
  • 4
  • [ 68500-37-8 ]
  • [ 3964-52-1 ]
  • 3-chloro-4-((7-methoxyquinolin-4-yl)oxy)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With sodium hydride; In dimethyl sulfoxide; mineral oil; at 150℃; for 2h;Microwave irradiation; To a mixture of 4-amino-2-chlorophenol (500 mg, 3.48 mmol) and 4-chloro- 7-methoxyquinoline (675 mg, 3.51 mmol) in DMSO (5 mL) was added NaH (335 mg, 7.12 mmol, 60percent in mineral oil) portion-wise. The reaction mixture was microwaved and stirred at 150 °C for 2 hours, then cooled to rt, quenched with water (50 mL) and extracted with EtOAc (100 mL x 3). The combined organic phases were washed with brine (80 mL), dried over anhydrous a2S04, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/PE (v/v) = 2/1) to give the title compound as an orange solid (345 mg, 42percent). MS (ESI, pos. ion) m/z: 301.0 [M+H]+; NMR (400 MHz, DMSO-i): delta 8.56 (d, J= 5.2 Hz, 1H), 8.21 (d, J= 9.2 Hz, 1H), 7.38 (d, J= 2.5 Hz, 1H), 7.26-7.29 (m, 1H), 7.09 (d, J= 8.7 Hz, 1H), 6.77 (d, J= 2.5 Hz, 1H), 6.62 (dd, J= 2.6 Hz, 8.7 Hz, 1H), 6.28 (d, J=2.5 Hz, 1H), 5.48 (s, 2H), 3.92 (s, 3H).
  • 5
  • [ 3964-52-1 ]
  • [ 704-91-6 ]
  • N-(3-chloro-4-hydroxyphenyl)-1H-indazole-6-carboxamide [ No CAS ]
  • 6
  • [ 3964-52-1 ]
  • [ 78078-92-9 ]
  • [ 397281-20-8 ]
  • 7
  • [ 3964-52-1 ]
  • [ 78078-92-9 ]
  • 4-amino-2-chlorophenyl-2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonate [ No CAS ]
 

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