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Product Details of [ 603-84-9 ]

CAS No. :603-84-9 MDL No. :MFCD11035882
Formula : C6H4ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QBGLHYQUZJDZOO-UHFFFAOYSA-N
M.W : 173.55 Pubchem ID :3013917
Synonyms :

Calculated chemistry of [ 603-84-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.3
TPSA : 66.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.2
Log Po/w (XLOGP3) : 2.07
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : -0.13
Consensus Log Po/w : 1.19

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.48 mg/ml ; 0.00277 mol/l
Class : Soluble
Log S (Ali) : -3.09
Solubility : 0.142 mg/ml ; 0.00082 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.81
Solubility : 2.66 mg/ml ; 0.0153 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 603-84-9 ]

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 [ 603-84-9 ]

* 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.

  • Upstream synthesis route of [ 603-84-9 ]
  • Downstream synthetic route of [ 603-84-9 ]

[ 603-84-9 ] Synthesis Path-Upstream   1~18

  • 1
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YieldReaction ConditionsOperation in experiment
62%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5 h;
Stage #2: With sulfuric acid; copper(l) chloride In water for 18 h;
Example 10 [:] Synthesis of [2-CHLORO-3- (2, 2-DIMETHYL-4-PHENETHYLSULFANYLMETHYL-1,] 2- dihydroquinoline-6-yl) phenol OH z O < \\ CI 8r OrB/ H H Suzuki OH OH ci ci \\I \\I I/ \\ \\ I \\ N N H H 10 To a suspension of 2-amino-3-nitrophenol (10 g, 65 mmol) in concentrated [HC1] (10 mL) at [0°C,] sodium nitrite (5.1 g, 73.3 mmol) in water (60 [ML)] was added dropwise. After stirring for 30 minutes at [0°C,] CuCl (12.8 g, [130] mmol) in 10percent [H2SO4] (3 mL) was added and the reaction was stirred for 18 hours. The heterogeneous mixture was filtered and washed with water. The filtrate was extracted three times with 70 mL portions of EtOAc. Evaporation of EtOAc extractions afforded 7 grams (62percent yield) of pure [2-CHLORO-3-NITROPHENOL,] 2-Chloro-3- nitrophenol (6 g, 35 mmol) was dissolved in methanol (100 [ML)] and treated with ammonium chloride (9.4 g, 175.7 mmol) and zinc dust (46 g, 702.8 mmol). The resulting mixture was refluxed for one hour. After filtration and evaporation, 2-chloro-3-aminophenol was collected (4.5 g, 90percent yield) as a purple solid. To a suspension of 2-chloro-3-aminophenol (4.5 g, 31 mmol) in concentrated [HCI] (10 mL) at [0°C] was added dropwise sodium nitrite (2.5 g, 35 mmol) in water (50 mL). After stirring for 30 minutes at [0°C,] [I (I] (10.4 g, 63 mmol) in 10percent [H2SO4] (3 mL) was added dropwise. The reaction was stirred at room temperature for 2 hours, then filtered, extracted with EtOAc, and concentrated in vacuo to afford 2-chloro-3-iodophenol as a dark purple solid (6 g, 75percent yield). 6-Bromo-2,2, [4-TRIMETHYL-1,] 2-dihydroquinoline (2.3 g, 9.2 mmol) (Example 8) and bis (pinacol) diborane (4.2 g, 16.5 mmol) were combined in DMSO (2 mL). [KOAC] (2.7 g, 27.4 mmol) was added, followed by [PDCL2] (dppf) (100 mg). The contents were placed into a microwave reaction vessel assembly and irradiated at [120°C] for 15 minutes. After cooling to room temperature, purification by chromatography afforded 2,2, [4-TRIMETHYL-6- (4,] 4,5, 5- tetramethyl- [1, 3,2] [DIOXABOROLAN-2-YL)-1,] 2-dihydroquinoline (2.3 g, [84percent] yield) as a white crystalline solid. 2,2, [4-TRIMETHYL-6- (4,] 4,5, [5-TETRAMETHYL- [1,] 3,2] [DIOXABOROLAN-2-YL)-1,] 2-dihydroquinoline [(308] mg) and 393 mg of 2-chloro-3-iodophenol were coupled using of 100 mg [OF PDCL2 (DPPF)] and [300 MG OF KOAC TO GIVE 250 MG OF 2-CHLORO-3- (2, 2, 4-TRIMETHYL-1, 2-DIHYDROQUINOLIN-6-YL) -] phenol. Using the procedures described in Example 7, this (85 mg) was reacted with NBS to give 56 mg [OF 3- (4-BROMOMETHYL-2, 2-DIMETHYL-1, 2-DIHYDROQUINOLIN-6-YL)-2-CHLOROPHENOL.] The product (50 mg) was coupled with 0.04 mL of 2-phenylethanethiol to give 40 mg of the title compound as an oil.
48%
Stage #1: With hydrogenchloride; sodium nitrite In 1,4-dioxane; water at 0 - 70℃; for 3.25 h;
Stage #2: With copper(l) chloride In 1,4-dioxane; water at 0 - 60℃; for 0.5 h;
2-Amino-3-nitrophenol B1 (5 g; 32.4 MMOL) was dissolved in concentrated HCI (75 ML) and 1,4-dioxane (14. 7 mL). The mixture was heated to 70 C UNTIL most of the solids were in solution. The reaction mixture was cooled to 0 C (ice bath), and sodium nitrite (2.23 g; 32.3 MMOL) in H20 (5.4 mL) was added over a period of 3 hours to the brown solution. The temperature was maintained BELOW 10 C during the addition and the stirring was continued for an additional 15 min at 0°C. This diazonium intermediate was poured into a solution of Cu (I) CI (3.8 g; 38.9 MMOL) in H20 (18. 5 mL) and conc. HCI (18.5 mL) at 0 C. The reaction was stirred for 15 min at 0 C, WARMED TO 60 C, and stirred for an additional 15 min The reaction mixture was then brought to room temperature, and left to stir overnight. The reaction mixture was transferred to a separatory funnel and extracted with ether (3X 150 mL). The organic layers were combined, washed with brine (1X), dried (NA2SO4), filtered and concentrated to afford the crude product (5.83 g) as a red-brown oil. The crude material was purified by flash column chromatography (1 : 25 ultra pure silica gel, 230-400 mesh, 40-60 MM, 60 angstroms; 3: 1 hexane/EtOAcas the solvent) to afford pure 2-chloro-3-nitrophenol C2 (48percent; 2.7 g) as an orange solid. MS 171. 8 (MH)- : Homogeneity by HPLC (TFA) 220 nm: 96percent. Relevant literature for the Sandmeyer Reaction: J. Med. Chem, 1982,25 (4), 446- 451.
48%
Stage #1: With hydrogenchloride In 1,4-dioxane; water at 70℃;
Stage #2: With sodium nitrite In 1,4-dioxane; water at 0 - 10℃; for 3.25 h;
Stage #3: With hydrogenchloride; copper(l) chloride In 1,4-dioxane; water at 0 - 60℃; for 0.5 h;
Step A:; 2-Amino-3-nitrophenol 1b1 (5 g; 32.4 mmol) was dissolved in concentratedHCI (75 ml) and 1,4-dioxane (14.7 ml). The mixture was heated to 70°C until most ofthe solids were in solution. The reaction mixture was cooled to 0°C (ice bath), andsodium nitrite (2.23 g; 32.3 mmol) in H2O (5.4 ml) was added over a period of 3 hoursto the brown solution. The temperature was maintained below 10°C during theaddition and the stirring was continued for an additional 15 min. at 0°C. Thisdiazonium intermediate was poured into a solution of Cu(l)CI (3.8 g; 38.9 mmol) inH2O (18.5 ml_) and cone. HCI (18.5 mL) at 0°C. The reaction was stirred for 15 min. at0°C, warmed to 60°C, and stirred for an additional 15 min. The reaction mixture wasthen brought to room temperature, and left to stir overnight. The reaction mixture wastransferred to a separatory funnel and extracted with ether (3 X 150 mL). The organiclayers were combined, washed with brine (1 X), dried (Na2SO4), filtered andconcentrated to afford the crude product (5.83 g) as a red-brown oil. The crudematerial was purified by flash column chromatography (1:25 ultra pure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; 3:1 hexane/EtOAc as the solvent) to afford pure2-chloro-3-nitrophenol 1c1 (48percent; 2.7 g) as an orange solid. MS 171.8 (MH)":Homogeneity by HPLC (TFA) (at) 220 nm: 96percent .
48%
Stage #1: With hydrogenchloride In 1,4-dioxane; water at 70℃;
Stage #2: With sodium nitrite In 1,4-dioxane; water at 0 - 10℃; for 3.25 h;
Stage #3: With copper(l) iodide In 1,4-dioxane; water at 0 - 60℃;
2-Amino-3-nitrophenol 2b1 (5 g; 32.4 mmol) was dissolved in concentratedHCI (75 ml) and 1,4-dioxane (14.7 ml_). The mixture was heated to 70°C until most ofthe solids were in solution. The reaction mixture was cooled to 0°C (ice bath), andsodium nitrite (2.23 g; 32.3 mmol) in H2O (5.4 ml) was added over a period of 3 hoursto the brown solution. The temperature was maintained below 10°C during theaddition and the stirring was continued for an additional 15 min. at 0°C. Thisdiazonium intermediate was poured into a solution of Cu(l)CI (3.8 g; 38.9 mmol) inH2O (18.5 ml) and cone. HCI (18.5 mL) at 0°C. The reaction was stirred for 15 min. at0°C, warmed to 60°C, and stirred for an additional 15 min. The reaction mixture wasthen brought to room temperature, and left to stir overnight. The reaction mixture wastransferred to a separatory funnel and extracted with ether (3 X 150 ml). The organiclayers were combined, washed with brine (1 X), dried (Na2SO4), filtered andconcentrated to afford the crude product (5.83 g) as a red-brown oil. The crudematerial was purified by flash column chromatography (1:25 ultra pure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; 3:1 hexane/EtOAc as the solvent) to afford pure2-chloro-3-nitrophenol 2c1 (48percent; 2.7 g) as an orange solid. MS 171.8 (MH)":Homogeneity by HPLC (TFA) (at) 220 nm: 96percent .Relevant literature for the Sandmeyer Reaction: J. Med. Chem, 1982, 25(4), 446-451.

Reference: [1] Patent: WO2004/18429, 2004, A2, . Location in patent: Page 86-87
[2] Patent: WO2004/103996, 2004, A1, . Location in patent: Page 42-43
[3] Patent: WO2006/7700, 2006, A1, . Location in patent: Page/Page column 63
[4] Patent: WO2006/85, 2006, A1, . Location in patent: Page/Page column 77
  • 2
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YieldReaction ConditionsOperation in experiment
69%
Stage #1: With hydrogenchloride In 1,4-dioxane at 70℃;
Stage #2: With sodium nitrite In water at 0℃; for 3 h;
Stage #3: With hydrogenchloride; copper(l) chloride In water at 0 - 60℃; for 0.5 h;
INTERMEDIATE PREPARATION 152-chloro-3-[ 1-methylethyl)oxy]aniline2-chloro-3-nitrophenolA mixture of 2-amino-3-nitrophenol (23.7 g, 154 mmol) was dissolved in concentrated HCI (356 mL, 4.27 mol) and 1 ,4-dioxane (70 mL) and heated to 70°C until most of the solids were in solution. The reaction mixture was cooled to 0°C and sodium nitrite (10.61 g, 154 mmol) in water (26.0 mL) was added over a period of 3 h. The temperature was maintained below 10°C during the addition and stirring was continued for an additional 15 min at 0°C. This diazonium intermediate was poured into a solution of copper(l) chloride (18.27 g, 185 mmol) in water (90 mL) and concentrated HCI (90 mL) at 0°C. The reaction was stirred for 15 min at 0°C, warmed to 60°C, and stirred for an additional 15 min. The reaction mixture was warmed to room temperature and stirred overnight. The mixture was transferred to a separatory funnel and extracted with Et20 (3 x 500 mL). The combined ethereal extracts were washed with brine, dried over Na2S04, filtered, and concentrated to afford the crude product. The crude material was purified via column chromatography (ISCO, 3:1hexanes/ethyl acetate) to give 2-chloro-3-nitrophenol (19.5 g, 69percent yield).
Reference: [1] Patent: WO2011/119704, 2011, A1, . Location in patent: Page/Page column 45-46
  • 3
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YieldReaction ConditionsOperation in experiment
32% With potassium chlorate In hydrogenchloride; dichloromethane; water; toluene 1.1.
2-Chloro-3-nitrophenol
73 g (0.52 mol) of 3-nitrophenol are dissolved in 2 liters-of 6N hydrochloric acid while heating.
The mixture is cooled in an ice bath to 28°-30° C. 32 g (0.26 mol) of potassium chlorate in 500 ml of water are added over 1.5 hours and then, at the end of the addition, the mixture is left stirring for 30 minutes at 28°-30° C.
The mixture is cooled to 15° C. and 1 liter of dichloromethane is added.
The layers are separated and the organic phase is washed with water.
The organic phase is dried and evaporated.
The residue is purified by chromatography on a column of silica gel, eluding with a dichloromethane/methanol (80/20) mixture.
Recrystallization is carried out from toluene. 29 g of product are obtained.
Melting point=130° C. Yield=32percent
Reference: [1] Patent: US5418241, 1995, A,
[2] Journal of the Indian Chemical Society, 1989, vol. 66, # 5, p. 301 - 303
[3] Chemische Berichte, 1893, vol. 26, p. 2466
[4] Journal of the Indian Chemical Society, 1989, vol. 66, # 5, p. 301 - 303
[5] Patent: WO2005/21547, 2005, A2, . Location in patent: Page/Page column 68-69
[6] Patent: WO2010/125103, 2010, A1, . Location in patent: Page/Page column 103
  • 4
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  • [ 610-78-6 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 928,933
[2] Journal fuer Praktische Chemie (Leipzig), 1930, vol. &lt;2&gt; 127, p. 20,22
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. &lt;2&gt; 127, p. 20,22
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1931, vol. &lt;2&gt; 129, p. 327,335
  • 7
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1931, vol. &lt;2&gt; 129, p. 327,335
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. &lt;2&gt; 127, p. 20,22
  • 9
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. &lt;2&gt; 127, p. 20,22
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1931, vol. &lt;2&gt; 129, p. 327,335
  • 11
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1931, vol. &lt;2&gt; 129, p. 327,335
  • 12
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. &lt;2&gt; 127, p. 20,22
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1931, vol. &lt;2&gt; 129, p. 327,335
  • 14
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. &lt;2&gt; 127, p. 20,22
  • 15
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Reference: [1] Journal of the Chemical Society, 1930, p. 928,933
  • 16
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Reference: [1] Chemische Berichte, 1893, vol. 26, p. 2466
  • 17
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  • [ 74-88-4 ]
  • [ 3970-39-6 ]
YieldReaction ConditionsOperation in experiment
98% With caesium carbonate In DMF (N,N-dimethyl-formamide) at 18 - 22℃; The nitrophenol starting material C2 (1.3 g; 7.49 MMOL) was dissolved in DMF (10 mL) and to this solution was added ground cesium carbonate (2.92 g; 8.96 MMOL), followed by Mel (1. 4 mL; 22. 5 MMOL). The mixture was stirred at room temperature overnight. The DMF was evaporated in vacuo and the residue taken up in ether (150 ML), washed with water (150 mL), brine (4x 100 mL), and then dried over (MGSO4) THE organic phase was filtered and evaporated to afford the crude 2- CHLORO-3-NITROANISOLE C3 (98percent; 1.38 g) as an orange solid. Homogeneity by HPLC (TFA) 220 nm: 93percent.
98% With caesium carbonate In N,N-dimethyl-formamide at 20℃; Step B:; The nitrophenol starting material 1c1 (1.3 g; 7.49 mmol) was dissolved inDMF (10 ml) and to this solution was added ground cesium carbonate (2.92 g; 8.96mmol), followed by Mel (1.4 ml; 22.5 mmol). The mixture was stirred at roomtemperature overnight. The DMF was evaporated in vacuo and the residue taken upin ether (150 ml), washed with water (150 ml), brine (4 X 100 mL), and then driedover (MgSO4). The organic phase was filtered and evaporated to afford the crude 2-chloro-3-nitroanisole 1c2 (98percent; 1.38 g) as an orange solid.
98% With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; The nitrophenol starting material 1c1 (1.3 g; 7.49 mmol) was dissolved in DMF (10 mL) and to this solution was added ground cesium carbonate (2.92 g; 8.96 mmol), followed by MeI (1.4 mL; 22.5 mmol). The mixture was stirred at room temperature overnight. The DMF was evaporated in vacuo and the residue taken up in ether (150 mL), washed with water (150 mL), brine (4.x.100 mL), and then dried over (MgSO4). The organic phase was filtered and evaporated to afford the crude 2-chloro-3-nitroanisole 1c2 (98percent; 1.38 g) as an orange solid.
98% With caesium carbonate In N,N-dimethyl-formamide at 20℃; The nitrophenol starting material 2c1 (1.3 g; 7.49 mmol) was dissolved inDMF (10 ml) and to this solution was added ground cesium carbonate (2.92 g; 8.96mmol), followed by Mel (1.4 ml; 22.5 mmol). The mixture was stirred at roomtemperature overnight. The DMF was evaporated in vacua and the residue taken upin ether (150 ml), washed with water (150 ml), brine (4 X 100 ml), and then driedover (MgSO4). The organic phase was filtered and evaporated to afford the crude 2-chloro-3-nitroanisole 2c2 (98percent; 1.38 g) as an orange solid.Homogeneity by HPLC (TFA) (at) 220nm: 93percent.

Reference: [1] Patent: WO2004/103996, 2004, A1, . Location in patent: Page 42-43
[2] Patent: WO2006/7700, 2006, A1, . Location in patent: Page/Page column 63
[3] Patent: US2006/19905, 2006, A1, . Location in patent: Page/Page column 25
[4] Patent: WO2006/85, 2006, A1, . Location in patent: Page/Page column 77
[5] Chemische Berichte, 1893, vol. 26, p. 2466
[6] Patent: WO2005/21547, 2005, A2, . Location in patent: Page/Page column 69
[7] Patent: WO2010/125103, 2010, A1, . Location in patent: Page/Page column 103
  • 18
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Reference: [1] Journal of the American Chemical Society, 1939, vol. 61, p. 2828
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