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[ CAS No. 385-01-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 385-01-3
Chemical Structure| 385-01-3
Chemical Structure| 385-01-3
Structure of 385-01-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 385-01-3 ]

CAS No. :385-01-3 MDL No. :MFCD07368753
Formula : C6H4FNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :GAWNBKUTBVLIPL-UHFFFAOYSA-N
M.W : 157.10 Pubchem ID :2782777
Synonyms :

Calculated chemistry of [ 385-01-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.25
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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : -0.35
Consensus Log Po/w : 0.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.07
Solubility : 1.33 mg/ml ; 0.00848 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.553 mg/ml ; 0.00352 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.47
Solubility : 5.34 mg/ml ; 0.034 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 385-01-3 ]

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 [ 385-01-3 ]

* 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 [ 385-01-3 ]
  • Downstream synthetic route of [ 385-01-3 ]

[ 385-01-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 19064-24-5 ]
  • [ 385-01-3 ]
YieldReaction ConditionsOperation in experiment
61% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 18.5 h; A solution of potassium TERT-BUTOXIDE (1.23 g, 11 mmol) in 25 mL of anhydrous DMSO was stirred at room temperature for 30 minutes and treated with 1, 3-difluoro-2-nitrobenzene (1.59 g, 10 mmol). After 18 hours, the mixture was diluted with 150 mL of 1 N aqueous sulfuric acid and extracted with three 50 mL portions of diethyl ether. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in 50 mL of trifluoroacetic acid. After 30 minutes at room temperature, the mixture was concentrated in vacuo, treated with 50 mL of 1 N aqueous sodium hydroxide, and extracted with three 30 mL portions of diethyl ether. The aqueous layer was acidified with 1 N aqueous sulfuric acid and extracted with two 50 mL portions of dichloromethane. The combined dichloromethane layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.3 g of 3-fluoro-2-nitrophenol as orange oil (61percent yield). An solution of 3-fluoro-2-nitrophenol (1.13 g, 7.2 mmol) and pyridine (0.65 mL, 8 mmol) in 15 mL of anhydrous dichloromethane was cooled in an ice bath and treated with a solution of triflic anhydride (1.33 mL, 7.9 mmol) in 3 mL of anhydrous dichloromethane. After 4 hours, the reaction mixture was diluted with 100 mL of dichloromethane, washed with two 30 mL portions of saturated aqueous sodium bicarbonate, two 30 mL portions of 1 N aqueous sulfuric acid, and two 30 mL portions of water, dried over sodium sulfate, filtered, and concentrated in VACUA TAO give 2 g of the title product as a light brown oil (96percent yield).
Reference: [1] Patent: WO2005/30213, 2005, A1, . Location in patent: Page/Page column 182-183
[2] Magnetic Resonance in Chemistry, 1996, vol. 34, # 6, p. 440 - 446
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 7, p. 623 - 634
[4] Patent: WO2011/106986, 2011, A1,
[5] ChemMedChem, 2017, vol. 12, # 17, p. 1436 - 1448
[6] Patent: US2010/94000, 2010, A1, . Location in patent: Page/Page column 29
  • 2
  • [ 641-49-6 ]
  • [ 385-01-3 ]
Reference: [1] ChemMedChem, 2017, vol. 12, # 17, p. 1436 - 1448
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 7, p. 623 - 634
[3] Patent: WO2011/106986, 2011, A1, . Location in patent: Page/Page column 119; 120
  • 3
  • [ 372-20-3 ]
  • [ 385-01-3 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 1881
[2] Journal of the Chemical Society, 1925, vol. 127, p. 1602[3] Journal of the Chemical Society, 1926, p. 159
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 22, p. 6842 - 6851
  • 4
  • [ 372-20-3 ]
  • [ 446-36-6 ]
  • [ 385-01-3 ]
  • [ 394-41-2 ]
YieldReaction ConditionsOperation in experiment
27% at 15 - 26℃; for 1.5 - 2 h; 3-Fluorophenol (5Og, 446mmol, lequiv) is dissolved glacial acetic acid (250 mL) and nitric acid 99percent (29.8g, 468mmol, 1.05equiv) is added slowly over approximately 1 h, maintaining the temperature at 20-250C. After complete addition, the reaction mixture is stirred for 30-60 min at ambient temperature and disappearance of 3-fluorophenol is confirmed by HPLC. The mixture is quenched by addition of water (500 mL). The resulting mixture is extracted with cyclohexane (4*67mL) to remove most of the regioisomers. The combined organic phases are extracted with water (167mL) to recover any desired regioisomer. The combined aqueous phases are extracted with TBME (3*167 mL) TBME to recover the desired product. The TBME phase, containing the desired regioisomer, is washed with a 10percent solution of sodium carbonate (4* 10OmL) to remove any acetic acid.TBME is replaced by toluene by distillation at atmospheric pressure, resulting in a solution of the product in approximately 100 mL of toluene. The solution is slowly cooled down to ambient temperature, which led to the precipitation of the desired product. The product was collected by filtration. The solid was dried in an oven overnight to give the title compound in 29percent yield and 97.9percent purity by HPLC. 1H-NMR (399.822 MHz, DMSO) δ 11.49 (s, IH), 8.07 (m, IH), 6.84-6.76 (m, 2H). 19F-NMR (376.209MHz, DMSO) δ - 114.28. m/z LCMS (ESI -ve) 156.00 (M-H); Method B: 3-Fluorophenol (1 mol equiv) is dissolved glacial acetic acid (2.5 rel vol) and nitric acid99percent (1.16 mol equiv) is added slowly over approximately 1 h, maintaining the temperature at 20-250C. After complete addition, the reaction mixture is stirred for Ih at ambient temperature and disappearance of 3-fluorophenol is confirmed by HPLC. The mixture is quenched by addition of water (2.5 rel vol). The resulting mixture is extracted 7 times with cyclohexane (1.675 rel vol) to remove most of the regioisomers. The combined organic phases are extracted with water (1 rel vol) to recover any desired regioisomer. The <n="21"/>combined aqueous phases are extracted twice with TBME (2.5 rel vol) to recover the desired product. The combined TBME phases, containing the desired regioisomer, are washed three times with a solution of 3percent aqueous potassium carbonate (1.25 rel vol) to remove any acetic acid. The TBME solution is concentrated at atmospheric pressure, then activated charcoal (0.017 rel weight) is added along with toluene (4.0 rel vol). The TBME is totally removed by atmospheric distillation. The warm solution at 50-800C is filtered over a filteraid to remove any insoluble particles. The toluene solution is then cooled to 0-50C which led to the precipitation of the desired product which was collected by filtration. The crude product was washed with toluene (0.17 rel vol) and petroleum ether (0.25 rel vol). The solid was dried in an oven overnight to give the title compound in 27percent yield and 97.4percent purity by HPLC.Crude 3-fluoro-4-nitrophenol (1 mol eq) is heated up to 110-115°C in toluene (3.24 rel vol) for 30 minutes. The mixture is cooled to 80-1000C and filtered over filteraid to remove any insoluble particles. The solution is further cooled to 0-50C which led to the precipitation of the desired product which was collected by filtration. The crude product was washed with toluene (0.17 rel vol). The solid was dried in an oven overnight to give the title compound in 77percent yield (recrystallisation only) and 99.2percent purity by HPLC. 1H-NMR (399.822 MHz, DMSO) δ 11.49 (s, IH), 8.07 (m, IH), 6.84-6.76 (m, 2H). 19F-NMR (376.209MHz, DMSO) δ -114.28. m/z LCMS (ESI -ve) 156.00 (M-H)
Reference: [1] Patent: WO2009/35407, 2009, A1, . Location in patent: Page/Page column 8; 19-20
  • 5
  • [ 372-20-3 ]
  • [ 7664-93-9 ]
  • [ 385-01-3 ]
  • [ 361-47-7 ]
  • [ 361-48-8 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 1881
[2] Journal of the Chemical Society, 1925, vol. 127, p. 1602[3] Journal of the Chemical Society, 1926, p. 159
  • 6
  • [ 372-20-3 ]
  • [ 446-36-6 ]
  • [ 385-01-3 ]
  • [ 394-41-2 ]
YieldReaction ConditionsOperation in experiment
27% at 15 - 26℃; for 1.5 - 2 h; 3-Fluorophenol (5Og, 446mmol, lequiv) is dissolved glacial acetic acid (250 mL) and nitric acid 99percent (29.8g, 468mmol, 1.05equiv) is added slowly over approximately 1 h, maintaining the temperature at 20-250C. After complete addition, the reaction mixture is stirred for 30-60 min at ambient temperature and disappearance of 3-fluorophenol is confirmed by HPLC. The mixture is quenched by addition of water (500 mL). The resulting mixture is extracted with cyclohexane (4*67mL) to remove most of the regioisomers. The combined organic phases are extracted with water (167mL) to recover any desired regioisomer. The combined aqueous phases are extracted with TBME (3*167 mL) TBME to recover the desired product. The TBME phase, containing the desired regioisomer, is washed with a 10percent solution of sodium carbonate (4* 10OmL) to remove any acetic acid.TBME is replaced by toluene by distillation at atmospheric pressure, resulting in a solution of the product in approximately 100 mL of toluene. The solution is slowly cooled down to ambient temperature, which led to the precipitation of the desired product. The product was collected by filtration. The solid was dried in an oven overnight to give the title compound in 29percent yield and 97.9percent purity by HPLC. 1H-NMR (399.822 MHz, DMSO) δ 11.49 (s, IH), 8.07 (m, IH), 6.84-6.76 (m, 2H). 19F-NMR (376.209MHz, DMSO) δ - 114.28. m/z LCMS (ESI -ve) 156.00 (M-H); Method B: 3-Fluorophenol (1 mol equiv) is dissolved glacial acetic acid (2.5 rel vol) and nitric acid99percent (1.16 mol equiv) is added slowly over approximately 1 h, maintaining the temperature at 20-250C. After complete addition, the reaction mixture is stirred for Ih at ambient temperature and disappearance of 3-fluorophenol is confirmed by HPLC. The mixture is quenched by addition of water (2.5 rel vol). The resulting mixture is extracted 7 times with cyclohexane (1.675 rel vol) to remove most of the regioisomers. The combined organic phases are extracted with water (1 rel vol) to recover any desired regioisomer. The <n="21"/>combined aqueous phases are extracted twice with TBME (2.5 rel vol) to recover the desired product. The combined TBME phases, containing the desired regioisomer, are washed three times with a solution of 3percent aqueous potassium carbonate (1.25 rel vol) to remove any acetic acid. The TBME solution is concentrated at atmospheric pressure, then activated charcoal (0.017 rel weight) is added along with toluene (4.0 rel vol). The TBME is totally removed by atmospheric distillation. The warm solution at 50-800C is filtered over a filteraid to remove any insoluble particles. The toluene solution is then cooled to 0-50C which led to the precipitation of the desired product which was collected by filtration. The crude product was washed with toluene (0.17 rel vol) and petroleum ether (0.25 rel vol). The solid was dried in an oven overnight to give the title compound in 27percent yield and 97.4percent purity by HPLC.Crude 3-fluoro-4-nitrophenol (1 mol eq) is heated up to 110-115°C in toluene (3.24 rel vol) for 30 minutes. The mixture is cooled to 80-1000C and filtered over filteraid to remove any insoluble particles. The solution is further cooled to 0-50C which led to the precipitation of the desired product which was collected by filtration. The crude product was washed with toluene (0.17 rel vol). The solid was dried in an oven overnight to give the title compound in 77percent yield (recrystallisation only) and 99.2percent purity by HPLC. 1H-NMR (399.822 MHz, DMSO) δ 11.49 (s, IH), 8.07 (m, IH), 6.84-6.76 (m, 2H). 19F-NMR (376.209MHz, DMSO) δ -114.28. m/z LCMS (ESI -ve) 156.00 (M-H)
Reference: [1] Patent: WO2009/35407, 2009, A1, . Location in patent: Page/Page column 8; 19-20
  • 7
  • [ 385-01-3 ]
  • [ 446-61-7 ]
Reference: [1] Journal of the American Chemical Society, 1932, vol. 54, p. 2973,2976
  • 8
  • [ 385-01-3 ]
  • [ 77-78-1 ]
  • [ 641-49-6 ]
Reference: [1] Journal of the American Chemical Society, 1932, vol. 54, p. 2973,2976
  • 9
  • [ 385-01-3 ]
  • [ 53981-23-0 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With tin(II) chloride dihdyrate; water In tetrahydrofuran at 80℃; for 0.666667 h;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water; ethyl acetate
Step 1. 2-amino-3-fluorophenolStannous chloride, dihydrate (0.724 g, 3.18 mmol) was added to a solution of 3-fluoro-2-nitrophenol (0.100 g, 0.636 mmol, SynQuest) in THF (5.0 mL), and water (5.0 mL) and the mixture was heated to 80° C. for 40 min. Upon cooling to RT, the reaction was diluted with ethyl acetate and saturated sodium bicarbonate solution. The mixture was then filtered to remove the insoluble material and the layers were separated. The aqueous layer was extracted with ethyl acetate three times. The extracts were washed with brine, dried over sodium sulfate, decanted and concentrated to afford product which was used without further purification (65 mg, 80percent). LCMS (M+H)+: 128.0.
Reference: [1] ChemMedChem, 2017, vol. 12, # 17, p. 1436 - 1448
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 7, p. 623 - 634
[3] Patent: US5886044, 1999, A,
[4] Patent: US5780483, 1998, A,
[5] Patent: US6262113, 2001, B1,
[6] Patent: US2010/298334, 2010, A1, . Location in patent: Page/Page column 45-46
[7] Patent: WO2011/106986, 2011, A1, . Location in patent: Page/Page column 120
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