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[ CAS No. 603-86-1 ]

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Chemical Structure| 603-86-1
Chemical Structure| 603-86-1
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CAS No. :603-86-1 MDL No. :MFCD00024233
Formula : C6H4ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :173.55 g/mol Pubchem ID :11784
Synonyms :

Safety of [ 603-86-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501 UN#:3077
Hazard Statements:H302-H315-H317-H318-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 603-86-1 ]

  • Upstream synthesis route of [ 603-86-1 ]
  • Downstream synthetic route of [ 603-86-1 ]

[ 603-86-1 ] Synthesis Path-Upstream   1~24

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Reference: [1] Environmental Science & Technology, 1994, vol. 28, # 2, p. 306 - 311
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YieldReaction ConditionsOperation in experiment
18% With nitric acid In acetic acid at 5℃; for 1.25 h; To a of solution of 2-chlorophenol (0.155 mol, 15.8 mL) in glacial acetic acid (42 mL) chilled to 5 °C, nitric acid (0.163 mol, 6.8 mL) was added dropwise over a period of 45 minutes with constant magnetic stirring. The reaction was maintained at 5 °C for thirty minutes then poured over ice (~250 mL). The black solid which forms during the reaction is removed by filtration. The resulting dark brown liquid was steam distilled providing a yellow soild which was recrystalized from water to give the title compound in an 18percent yield.
Reference: [1] Chinese Chemical Letters, 2010, vol. 21, # 4, p. 403 - 406
[2] Synthetic Communications, 2011, vol. 41, # 20, p. 2985 - 2992
[3] Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3435 - 3450
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3521 - 3525
[5] Journal of the Chemical Society, 1927, p. 1692
[6] Yakugaku Zasshi, 1925, # 517, p. 15[7] Chem. Zentralbl., 1926, vol. 97, # I, p. 80
[8] Patent: CN104262159, 2016, B,
[9] Patent: CN105085275, 2017, B,
[10] Patent: CN107915677, 2018, A, . Location in patent: Paragraph 0013; 0014
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YieldReaction ConditionsOperation in experiment
92% With silica supported Al(NO3)3*9H2O In acetone at 20℃; for 0.416667 h; General procedure: To a solution of phenol (1 mmol) in acetone (5 mL) wasadded silica supported Al(NO3)3·9H2O (1 mmol) and theresulting mixture stirred at room temperature. After completionof the reaction, as indicated by TLC, the reaction masswas filtered and the residue (silica) was washed with ethylacetate (2 5 mL). The filtrate and the washing were collectivelyconcentrated under reduced pressure, and the crudecompound was purified by column chromatography oversilica gel (100-200 mesh) to afford the pure ortho-nitro phenol(95percent) and para- nitro phenol (3percent).
36% With nickel(II) nitrate hexahydrate In tetrahydrofuran at 50℃; for 4 h; General procedure: A suspension of 2-methylphenol(18.5 mmol, 1.0 eq) and Cu(NO3)2.3H2O (27.7 mmol, 1.5 eq) in THF was stirred magnetically at 60°C or reflux for several hours. Then after the solvent was removed under vacuum, the mixture was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (5mL), dried over anhydrous MgSO4 and concentrated under vacuum. The crude residue was purified by column chromatography to afford the product (67-90percent).
Reference: [1] Letters in Organic Chemistry, 2015, vol. 12, # 2, p. 129 - 135
[2] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 10, p. 973 - 977
[3] International Journal of Chemical Kinetics, 2016, vol. 48, # 4, p. 171 - 196
[4] Synthetic Communications, 2003, vol. 33, # 6, p. 961 - 966
[5] European Journal of Organic Chemistry, 2005, # 11, p. 2379 - 2384
[6] Tetrahedron, 1989, vol. 45, # 5, p. 1415 - 1422
[7] Tetrahedron, 2005, vol. 61, # 46, p. 10861 - 10867
[8] Tetrahedron, 2005, vol. 61, # 46, p. 10861 - 10867
[9] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 10, p. 973 - 977
[10] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 10, p. 973 - 977
[11] Journal of Organic Chemistry, 2005, vol. 70, # 22, p. 9071 - 9073
[12] Arkivoc, 2014, vol. 2014, # 5, p. 64 - 71
[13] Journal of the American Chemical Society, 1982, vol. 104, # 23, p. 6470 - 6471
[14] Roczniki Chemii, 1930, vol. 10, p. 761,765,771[15] Chem. Zentralbl., 1931, vol. 102, # I, p. 1427
[16] Chemische Berichte, 1872, vol. 5, p. 778[17] Justus Liebigs Annalen der Chemie, 1874, vol. 173, p. 306
[18] Tetrahedron, 1989, vol. 45, # 5, p. 1299 - 1310
[19] Journal of the American Chemical Society, 1934, vol. 56, p. 1787,1790
[20] Quarterly Journal of Pharmacy and Pharmacology, 1945, vol. 18, p. 41,43
[21] Journal of the American Chemical Society, 1934, vol. 56, p. 1787,1790
[22] Quarterly Journal of Pharmacy and Pharmacology, 1945, vol. 18, p. 41,43
[23] Chemische Berichte, 1872, vol. 5, p. 778[24] Justus Liebigs Annalen der Chemie, 1874, vol. 173, p. 306
[25] Tetrahedron, 1989, vol. 45, # 5, p. 1299 - 1310
[26] South African Journal of Chemistry, 2006, vol. 59, p. 93 - 96
[27] Synthetic Communications, 2013, vol. 43, # 19, p. 2672 - 2677
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Reference: [1] Liebigs Annalen der Chemie, 1994, # 3, p. 269 - 276
[2] Patent: EP1772493, 2007, A1, . Location in patent: Page/Page column 43
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Reference: [1] Synthetic Communications, 2002, vol. 32, # 2, p. 279 - 286
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Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 13, p. 4199 - 4208
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2481 - 2486
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 23, p. 11508 - 11516
[2] Patent: CN104262159, 2016, B,
[3] Patent: CN105085275, 2017, B,
  • 9
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2481 - 2486
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Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 4979 - 4981
[2] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 720 - 726[3] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 4, p. 806 - 814
[4] Journal of Organic Chemistry, 1998, vol. 63, # 13, p. 4199 - 4208
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Reference: [1] Patent: DE116790, , ,
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 9, p. 1662 - 1665
[2] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 9, p. 1662 - 1665
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Reference: [1] Roczniki Chemii, 1930, vol. 10, p. 761,765,771[2] Chem. Zentralbl., 1931, vol. 102, # I, p. 1427
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Reference: [1] Patent: CN107915677, 2018, A,
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Reference: [1] Roczniki Chemii, 1930, vol. 10, p. 761,765,771[2] Chem. Zentralbl., 1931, vol. 102, # I, p. 1427
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Reference: [1] Roczniki Chemii, 1930, vol. 10, p. 761,765,771[2] Chem. Zentralbl., 1931, vol. 102, # I, p. 1427
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 720 - 726[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 4, p. 806 - 814
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Reference: [1] Justus Liebigs Annalen der Chemie, 1874, vol. 173, p. 303
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Reference: [1] Roczniki Chemii, 1930, vol. 10, p. 761,765,771[2] Chem. Zentralbl., 1931, vol. 102, # I, p. 1427
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Reference: [1] Justus Liebigs Annalen der Chemie, 1874, vol. 173, p. 303
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YieldReaction ConditionsOperation in experiment
98% at 20℃; for 4 h; First, NaBH4 (1 mmol) was used as a reducing agent forthe conversion of Ag (+ 1) to Ag (0) in methanol at roomtemperature for 2 h. After that, the Ag/MMT was filtered andused as a catalyst. Then, in a typical procedure, a mixtureof 4-nitrophenol (0.1 mmol), KOH (0.15 mmol), isopropylalcohol (3 mL), and Ag/MMT catalyst (50 mg) 1.01 wtpercentwas stirred at room temperature for an appropriate time(Scheme 2). After the completion of the reaction (monitoredby GC), the catalyst was separated by filtration. The ensuingproduct was extracted with ethyl acetate and repeatedlywashed with water (3–4 times) to remove KOH. The resultingsolvent was evaporated to dryness in vacuum.
59% With hydrogenchloride; tin(II) chloride dihdyrate In ethanol for 24 h; Inert atmosphere Stannous chloride (74.76 mmol, 16.87 g) in concentrated HCl (28.5 mL) was added to a of solution of 2-chloro-6-nitrophenol (KR-400Cl) (29.90 mmol,5.19 g) in ethanol (215 mL) with constant magnetic stirring under argon atmosphere. After 24 hours the reaction was placed on ice and the pH was adjusted to 10 with 1M NaOH. The white precititate was removed by filtration and washed with methanol (40 mL). The filtrate was concentrated in vacuo, redissolved in dichloromethane (75 mL), washed over water (70 mL) and brine(70 mL) respectively, and dried over sodium sulfate. The dichloromethane layer was concentrated under reduced pressure, and silica gel column chromatography of the brown solid (10:1 hexanes/ethyl acetate) provided a crystalline brown solid in a 59percent yield.
55% at 80℃; for 18 h; 2-Chloro-6-nitrophenol (1.05 g, 6.03 mmol) and tin powder (2.32 g, 19.5 mmol) were stirred in glacial acetic acid at 80°C.After 18 h, the reaction was diluted with H2O (120 mL), filtered, and the filtrate extracted with EtOAc (1x100 mL, then 2x50 mL).The combined organics were washed with brine (3x50 mL), dried over Na2SO4, filtered, and concentrated.Flash chromatographic purification over silica (2:1 hexanes:EtOAc) afforded 2-amino-6-chlorophenol as a tannish-white crystalline solid (476 mg, 55percent).1H-NMR (500 MHz, CDCl3)d6.73 (dd,J=1.7, 8.1 Hz, 1H), 6.69 (t,J=7.8 Hz, 1H), 6.62 (dd,J=1.7, 7.7 Hz, 1H), 5.46 (br s, 1H), 3.84 (br s, 2H);13C-NMR (125 MHz, CDCl3)d139.32, 135.73, 121.28, 119.87, 118.31, 114.42; ESI-MS 144m/z[MH]+,C6H7ClNO requires 144.
Reference: [1] Liebigs Annalen der Chemie, 1994, # 3, p. 269 - 276
[2] Journal of the Iranian Chemical Society, 2018, vol. 15, # 2, p. 281 - 291
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 7974 - 7985
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3521 - 3525
[5] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3441 - 3449
[6] Biochemical Journal, 1947, vol. 41, p. 534,541
[7] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 2730 - 2735[8] Zhurnal Obshchei Khimii, 1960, vol. 30, # 8, p. 2748 - 2754
[9] Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3435 - 3450
[10] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 10, p. 3515 - 3523
[11] Patent: WO2007/70173, 2007, A2, . Location in patent: Page/Page column 94-95
[12] Patent: US2007/197512, 2007, A1, . Location in patent: Page/Page column 89
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YieldReaction ConditionsOperation in experiment
58% With hydrogenchloride In ethanol a
2-Amino-6-chlorophenol
A solution of 2-chloro-6-nitrophenol (1.210 g, 6.972 mmol) in ethanol (50 mL) was treated with iron powder (1.947 g, 34.86 mmol) and concentrated HCl (3 mL).
The yellow mixture was heated to reflux for 18 h and then cooled to room temperature.
The reaction mixture was filtered through a pad of Celite, and the filtrate was neutralized with satd aq NaHCO3 solution.
The resulting gray suspension was filtered through a pad of Celite, and the filtrate was extracted with ethyl acetate (3*20 mL).
The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give a black solid.
Trituration with heptane afforded 2-amino-6-chlorophenol (0.577 g, 58percent) as a dark brown solid. RP-HPLC (25 to 100percent CH3CN in 0.1 N aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 100 Å, 5 μm, 250*4.6 mm column) tr=7.30 min., 91percent; m/z 143
58% With hydrogenchloride In ethanol a)
2-amino-6-chlorophenol
A solution of 2-chloro-6-nitrophenol (1.210 g, 6.972 mmol) in ethanol (50 mL) was treated with iron powder (1.947 g, 34.86 mmol) and concentrated HCl (3 mL).
The yellow mixture was heated to reflux for 18 h and then cooled to room temperature.
The reaction mixture was filtered through a pad of Celite, and the filtrate was neutralized with satd aq NaHCO3 solution.
The resulting gray suspension was filtered through a pad of Celite, and the filtrate was extracted with ethyl acetate (3*20 mL).
The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give a black solid.
Trituration with heptane afforded 2-amino-6-chlorophenol (0.577 g, 58percent) as a dark brown solid. RP-HPLC (25 to 100percent CH3CN in 0.1 N aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 100 Å, 5 μm, 250*4.6 mm column) tr=7.30 min., 91percent; m/z 143 (MH+).
Reference: [1] Patent: US2002/156081, 2002, A1,
[2] Patent: US6921763, 2005, B2,
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Reference: [1] Patent: CN107915677, 2018, A, . Location in patent: Paragraph 0013; 0014
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Reference: [1] Journal of the Chemical Society, 1930, p. 2166,2168
[2] Journal of the American Chemical Society, 1934, vol. 56, p. 1787,1790
[3] Journal of the Chemical Society, 1927, p. 1692
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