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[ CAS No. 1283718-57-9 ] {[proInfo.proName]}

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Product Details of [ 1283718-57-9 ]

CAS No. :1283718-57-9 MDL No. :MFCD16658266
Formula : C9H9FO3 Boiling Point : -
Linear Structure Formula :- InChI Key :TWPVBTPPDZHBRQ-UHFFFAOYSA-N
M.W : 184.16 Pubchem ID :66712858
Synonyms :

Calculated chemistry of [ 1283718-57-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.81
TPSA : 46.53 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) : -6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 0.93
Log Po/w (WLOGP) : 1.37
Log Po/w (MLOGP) : 1.79
Log Po/w (SILICOS-IT) : 1.98
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.71
Solubility : 3.58 mg/ml ; 0.0194 mol/l
Class : Very soluble
Log S (Ali) : -1.49
Solubility : 5.91 mg/ml ; 0.0321 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.481 mg/ml ; 0.00261 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 1283718-57-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1283718-57-9 ]

* 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.

  • Downstream synthetic route of [ 1283718-57-9 ]

[ 1283718-57-9 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 452-74-4 ]
  • [ 1283718-57-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tert.-butyl lithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: sulfuric acid / 90 °C 3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 20 - 100 °C 4.1: sodium acetate / 150 °C 5.1: potassium hydroxide / methanol / 90 °C / Reflux
  • 2
  • [ 7697-23-6 ]
  • methyl 2-fluoro-4-(hydroxymethyl)benzoate [ No CAS ]
  • 3
  • [ 74733-29-2 ]
  • [ 1283718-57-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 20 - 100 °C 2: sodium acetate / 150 °C 3: potassium hydroxide / methanol / 90 °C / Reflux
  • 4
  • [ 85070-57-1 ]
  • [ 1283718-57-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium acetate / 150 °C 2: potassium hydroxide / methanol / 90 °C / Reflux
  • 5
  • [ 1628151-55-2 ]
  • [ 1283718-57-9 ]
YieldReaction ConditionsOperation in experiment
2.32 g With potassium hydroxide In methanol at 90℃; Reflux; 12.4 Synthesis of 4-Hydroxyomethyl-2-fluoro-benzoic acid In a 250 ml one-neck round bottom flask, equipped with a magnetic stir bar and condenser was added 2-fluoro-4-bromomethyl methyl benzoate (5.94 g, 24.04 mmol), 70 ml of acetic anhydride and sodium acetate (2.56 g, 31.26 mmol). The reaction was heated at 150 °C overnight. The reaction was cooled to room temperature and checked by TLC. 200 ml of water was added carefully, and the reaction mixture was transferred to separatory funnel. The aqueous phase was extracted with ether 2 x 100 ml and ethyl acetate 3 x 100 ml. The organic fractions were combined and concentrated. The residue was dissolved in 50 ml of methanol and transferred into 250 iil one-iieck flask equipped with a magnetic stir bar. Potassium hydroxide (6.75 g, 120 mmol) was dissolved in 20 ml methanol and added into the reaction flask, and the reaction mixture was heated at 90°C for overnight. The reaction was cooled to room temperature and checked by TLC. 100 ml of water was added carefully and the reaction mixture was carefully acidified with 3M HC1 solution until pH<2. The aqueous phase was extracted with ethyl acetate. The organic phase was concentrated and purified on an ISCO system using an ethyl acetate/hexane gradient to give 2.32 g of IXS-4-60-2. ‘H NMR (CDC13, 400 MHz) Overall yield is 57.0%. ‘H NMR (CDC13, 400 MHz) 6 13.02 (bs, 1H), 7.80 (t, 1H), 7.21 (t, 2H), 5.44 (bs, 1H), 4.45 (s, 2H).
  • 6
  • [ 164149-28-4 ]
  • methyl 2-fluoro-4-(hydroxymethyl)benzoate [ No CAS ]
  • 7
  • [ 175596-01-7 ]
  • methyl 2-fluoro-4-(hydroxymethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With water; acetic acid; at 15 - 25℃; under 15001.5 Torr; for 18h;Inert atmosphere; Step (ii) Raney nickel (2.0 g) was added to a solution of <strong>[175596-01-7]methyl 4-cyano-2-fluorobenzoate</strong> (obtained as described in step (i) above) (10.1 g, 61.6 mmol) in acetic acid (200 ml.) and water (100 niL). The mixture was stirred at RT under argon at 20 bar. After 18 h the mixture was filtered through diatomaceous earth, washing through with water (1000 mL). The filtrate was extracted with EtOAc (3 chi 300 mL). The combined organic phases were dried and concentrated, adding toluene to assist removal of acetic acid, to give methyl 2- 11 uoro-4-( hydroxy meth) l)benzoate (crude, 6.06 g) which was used in the next step without further purification or characterisation.
With nickel; acetic acid; In water; acetic acid; at 20℃; under 15001.5 Torr; for 18h;Inert atmosphere; Step (ii) Raney nickel (2.0 g) was added to a solution of <strong>[175596-01-7]methyl 4-cyano-2-fluorobenzoate</strong> (obtained as described in step (i) above) (10.1 g, 61.6 mmol) in acetic acid (200 mL) and water (100 mL). The mixture was stirred at RT under argon at 20 bar. After 18 h the mixture was filtered through diatomaceous earth, washing through with water (1000 mL). The filtrate was extracted with EtOAc (3*300 mL). The combined organic phases were dried and concentrated, adding toluene to assist removal of acetic acid, to give methyl 2-fluoro-4-(hydroxymethyl)benzoate (crude, 6.06 g) which was used in the next step without further purification or characterisation.
  • 8
  • methyl 2-fluoro-4-(hydroxymethyl)benzoate [ No CAS ]
  • [ 85070-58-2 ]
YieldReaction ConditionsOperation in experiment
With manganese(IV) oxide; In tetrahydrofuran; chloroform; at 15 - 60℃; for 4h; Step (iii)Methyl 2-fluoro-4-(hydroxymethyl)benzoate (step (ii) above) (1 g, 5.4 mmol) was dissolved in chloroform (40 mL) and TUP (5 mL). Manganese(IV) oxide (2.36 g, 27 mmol) was added and the mixture stirred at RT for 2 h and then at 60 C for 1 h. Further manganese(IV) oxide (2.36 g, 27 mmol) was added and heating was continued at 60 C. After 1 h the mixture was filtered through diatomaceous earth to give methyl 2-fluoro-4- formylbenzoate which was used without further purification. NMR (300 MHz, CDCI3) delta ppm 3.95 (s, 3H) 7.58-7.62 (m, 1H) 7.63-7.67 (m, 1 H) 8.08- 8.12 (m, 1H) 10.04 (s, 1H)
With manganese(IV) oxide; In tetrahydrofuran; chloroform; at 60℃; for 19h; Step (iii) Methyl 2-fluoro-4-(hydroxymethyl)benzoate (step (ii) above) (1 g, 5.4 mmol) was dissolved in chloroform (40 mL) and THF (5 mL). Manganese(IV) oxide (2.36 g, 27 mmol) was added and the mixture stirred at RT for 2 h and then at 60 C. for 1 h. Further manganese(IV) oxide (2.36 g, 27 mmol) was added and heating was continued at 60 C. After 18 h the mixture was filtered through diatomaceous earth to give methyl 2-fluoro-4-formylbenzoate which was used without further purification. 1H NMR (300 MHz, CDCl3) delta ppm 3.95 (s, 3H) 7.58-7.62 (m, 1H) 7.63-7.67 (m, 1H) 8.08-8.12 (m, 1H) 10.04 (s, 1H)
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 50℃; for 0.5h; (2) To a solution of the Compound 2 (2.53 g) in dimethylsulfoxide (40 mE) was added 2-iodoxybenzoic acid (4.59 g), and the resulting mixture was stirred at 500 C. for 30 minutes. The reaction mixture was allowed to cool to room temperature, and then water and ethyl acetate were added thereto, and the resulting mixture was stirred. The resulting insoluble matters were removed by filtration, and the resulting filtrate was extracted with ethyl acetate. The resulting organic layers were washed with water and saturated brine, dried, and concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 75:25). To a solution of the resulting compound in dichioromethane (20 mE) was added dropwise bis(2-methoxyethyl)aminosulthr trifluoride (2.64 mE) under ice-cooling, and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residues were purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 80:20) to give the Compound 4 (2.18 g) as a colorless powder. MS (APCI): mlz 205 [M+H]
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 50℃; for 0.5h; (2) Compound 2 (2.53 g)Of dimethylsulfoxide (40 mL)To the solution was added 2-iodoxybenzoic acid (4.59 g)Is added,Followed by stirring at 50 C. for 30 minutes.The reaction mixture was allowed to cool to room temperature,Water and ethyl acetate were added and stirred.Insolubles were removed by filtration,The filtrate was extracted with ethyl acetate.The obtained organic layer was washed with water and saturated brine,Dried and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5 to 75: 25).The obtained compound was dissolved in dichloromethane(2 mL) was added bis (2-methoxyethyl) aminosulfur trifluoride (2.64 mL) under ice-cooling,Was added dropwise,And the mixture was stirred at room temperature for 3 hours.The reaction mixture was concentrated under reduced pressure,The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5 to 80:20)Compound 4 (2.18 g)As a colorless powder.

  • 9
  • [ 153556-42-4 ]
  • [ 1283718-57-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: borane / tetrahydrofuran / 0 - 70 °C 1.2: 2 h / 25 °C 2.1: 1H-imidazole / dichloromethane / 0 - 25 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine / 65 °C / 2585.81 Torr 4.1: acetic acid / water; tetrahydrofuran / 25 °C
  • 10
  • [ 222978-01-0 ]
  • methyl 2-fluoro-4-(hydroxymethyl)benzoate [ No CAS ]
  • 11
  • [ 1017598-60-5 ]
  • [ 1283718-57-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine / 65 °C / 2585.81 Torr 2: acetic acid / water; tetrahydrofuran / 25 °C
  • 12
  • [ 2227018-10-0 ]
  • [ 1283718-57-9 ]
YieldReaction ConditionsOperation in experiment
3.2 g With acetic acid In tetrahydrofuran; water at 25℃; methyl 2-fluoro-4-(hydroxymethyl)benzoate (SI-6) A solution of compound SI-5 (4.94 g, 16.6 mmol) in AcOH/H2O/THF (13:7:3, 46 mL) was stirred at room temperature overnight. Then, the mixture was concentrated and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product which was purified by column chromatography to obtain pure compound SI-6 (3.2 g, 99% crude) as a white solid. ESI-MS m/z 185 [M+H]+ calc. for C9H9FO3. This intermediate was used in the next step without further characterization.
  • 13
  • [ 1283718-57-9 ]
  • [ 85070-57-1 ]
YieldReaction ConditionsOperation in experiment
19% With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 25℃; methyl 4-(bromomethyl)-2-fluoro-benzoate (Int. 2) To a solution of compound SI-6 (3.2 g, 17.4 mmol) and PPh3 (1.38 g, 5.3 mmol) in CH2Cl2(50 mL) was added NBS (3.7 g, 21 mmol) at 0 oC and then the solution was stirred at roomtemperature overnight. Then, the reaction was quenched with water and extracted withCH2Cl2. The organic layer was washed with brine, dried over anhydrous Na2SO4, filteredand concentrated to give the crude product which was purified by column chromatographyto obtain Int. 2 (0.83 g, 19%) as a white solid. ESI-MS m/z 247 [M+H]+ calc. forC9H8BrFO2. This intermediate was used in the next step without further characterization.
  • 14
  • [ 1283718-57-9 ]
  • [ 2227313-08-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 0 - 25 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1 h / 85 °C / Microwave irradiation
  • 15
  • [ 1283718-57-9 ]
  • [ 2227313-15-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 0 - 25 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1 h / 85 °C / Microwave irradiation 3: lithium hydroxide monohydrate / water; methanol; tetrahydrofuran / 25 °C
  • 16
  • [ 1283718-57-9 ]
  • [ 2227008-11-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 0 - 25 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1 h / 85 °C / Microwave irradiation 3: lithium hydroxide monohydrate / water; methanol; tetrahydrofuran / 25 °C 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 25 °C
  • 17
  • [ 1283718-57-9 ]
  • [ 1624792-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 0 - 25 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1 h / 85 °C / Microwave irradiation 3: lithium hydroxide monohydrate / water; methanol; tetrahydrofuran / 25 °C 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 25 °C 5: hydrogenchloride / ethyl acetate / 3 h / 25 °C
  • 18
  • [ 67-56-1 ]
  • [ 214554-18-4 ]
  • methyl 2-fluoro-4-(hydroxymethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.28 g With hydrogenchloride; In water; for 7.0h;Reflux; To a solution of the Compound 1(5.5 g) in methanol (120 mE) was added concentrated hydrochloric acid (12 mE), and the resulting mixture was heated under reflux for 7 hours. The reaction mixture was allowed to cool to room tempera- tare, and then concentrated under reduced pressure. The resulting concentrated residues were added dropwise toice-cooled saturated aqueous solution of sodium hydrogen carbonate, and the resulting mixture was stirred, and then extracted with chloroform. The resulting organic layers were dried, and then concentrated under reduced pressure. The resulting residues were purified by silica gel colunm chromatography (hexane:ethyl acetate=80:20 to 50:50) to give the Compound 2 (5.28 g) as a colorless powdet MS (APCI):mlz 185 [M+H]
5.28 g With hydrogenchloride; for 7.0h;Reflux; (1) Methanol (120 mL) of the compound 1 (5.5 g)Concentrated hydrochloric acid (12 mL) was added to the solution,And heated under reflux for 7 hours.The reaction mixture was allowed to cool to room temperature,And concentrated under reduced pressure.The concentrated residue was added dropwise to an ice-cooled saturated sodium bicarbonate aqueous solution and stirred,And extracted with chloroform.After drying the obtained organic layer,And concentrated under reduced pressure.The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 80: 20 to 50: 50)Compound 2 (5.28 g)As a colorless powder.
  • 19
  • [ 1283718-57-9 ]
  • [ 1270981-54-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / tetrahydrofuran / 3 h / 20 °C / Cooling with ice
Multi-step reaction with 2 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 3 h / 20 °C / Cooling with ice
  • 20
  • [ 1283718-57-9 ]
  • [ 2098741-37-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / tetrahydrofuran / 3 h / 20 °C / Cooling with ice 3: lithium borohydride / tetrahydrofuran / 3 h / 50 °C
Multi-step reaction with 3 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 3 h / 20 °C / Cooling with ice 3: lithium borohydride / tetrahydrofuran / 3 h / 50 °C
  • 21
  • [ 1283718-57-9 ]
  • [ 875222-54-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / tetrahydrofuran / 3 h / 20 °C / Cooling with ice 3: lithium borohydride / tetrahydrofuran / 3 h / 50 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C
Multi-step reaction with 4 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 3 h / 20 °C / Cooling with ice 3: lithium borohydride / tetrahydrofuran / 3 h / 50 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C
  • 22
  • [ 1283718-57-9 ]
  • [ 2098741-38-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / tetrahydrofuran / 3 h / 20 °C / Cooling with ice 3: lithium borohydride / tetrahydrofuran / 3 h / 50 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 5: potassium carbonate / 1-methyl-pyrrolidin-2-one / 2 h / 130 °C
Multi-step reaction with 5 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 3 h / 20 °C / Cooling with ice 3: lithium borohydride / tetrahydrofuran / 3 h / 50 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 0.5 h / 50 °C 5: potassium carbonate / 1-methyl-pyrrolidin-2-one / 2 h / 130 °C
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