Home Cart 0 Sign in  

[ CAS No. 288385-99-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 288385-99-9
Chemical Structure| 288385-99-9
Structure of 288385-99-9 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 288385-99-9 ]

Related Doc. of [ 288385-99-9 ]

Alternatived Products of [ 288385-99-9 ]
Product Citations

Product Details of [ 288385-99-9 ]

CAS No. :288385-99-9 MDL No. :MFCD11977234
Formula : C10H10FNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :VGDKNHRINLDMIS-UHFFFAOYSA-N
M.W : 227.19 Pubchem ID :22030743
Synonyms :

Calculated chemistry of [ 288385-99-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.49
TPSA : 72.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.06
Log Po/w (SILICOS-IT) : 0.84
Consensus Log Po/w : 1.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.54 mg/ml ; 0.00677 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.626 mg/ml ; 0.00275 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.93
Solubility : 0.265 mg/ml ; 0.00117 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 288385-99-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 288385-99-9 ]

* 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 [ 288385-99-9 ]

[ 288385-99-9 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 121247-16-3 ]
  • [ 288385-99-9 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate; In methanol; for 3h;Heating / reflux; A mixture of 1-(2,3-difluoro-6-nitrophenyl) -propan-2-one (183 g) and potassium carbonate (100 g) in methanol (1L) was heated at reflux for 3 h. The reaction mixture was then cooled and concentrated in vacuo to remove most of the methanol. The residue was diluted with ethyl acetate (1L), filtered and washed with water. The separated aqueous layer was neutralized with 2N HCl and extracted with ethyl acetate (2x500 mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to give a brown solid. The solid was triturated with diethyl ether and filtered to provide 1-(2-fluoro-3-methoxy-6-nitrophenyl)-propan-2-one (121 g, 71 %) as a yellow solid. LC/MS; (M+H)+ = 228.2
  • 2
  • [ 288385-99-9 ]
  • [ 649736-31-2 ]
YieldReaction ConditionsOperation in experiment
96% With pyridine hydrochloride; at 20 - 180℃; for 1.25h;Heating / reflux; A mixture of 1-(2-fluoro-3-methoxy-6-nitrophenyl)-propan-2-one from previous step (454 mg, 21 mmol) and pyridinium chloride (0.9 g, 7.8 mmol) was stirred at 180 C for 75 min. The reaction was cooled to room temperature, diluted with 1N HCl (3mL) and ethyl acetate (10 mL) and filtered. The filtrate was washed with brine (2x), dried and concentrated in vacuo to give 1-(2-fluoro-3-hydroxy-6-nitrophenyl)-propan-2-one (410 mg, 96 %) as a grey solid, which was used without further purification for the next step. LC/MS; (M+H)+ = 214. 1H NMR (CDCl3): delta 2.37 (s, 3H), 4.22 (s, 2H), 6.95 (dd, 1H), 7.95 (d, 1H, J= 9.35 Hz)
  • 3
  • [ 288385-99-9 ]
  • aqueous ammonium acetate [ No CAS ]
  • [ 7705-07-9 ]
  • [ 288385-93-3 ]
YieldReaction ConditionsOperation in experiment
90% In water; acetone; To a solution of <strong>[288385-99-9]3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene</strong> (11.36 g, 50 mmol) in acetone (200 ml) was added 4M aqueous ammonium acetate (700 ml) followed by a solution of titanium trichloride (15% in water, 340 ml) dropwise. The mixture was stirred for 10 minutes at ambient temperature and the mixture was extracted with ether. The organic layer was washed with 0.5N aqueous sodium hydroxide followed by water, brine, dried MgSO4) and the volatiles were removed under vacuum. The residue was purified by column chromatography eluding with methylene chloride to give 4-fluoro-5-methoxy-2-methylindole (8.15 g, 90%). 1H NMR Spectrum: (DMSO) 2.35 (s, 3H); 3.8 (s, 3H); 6.1 (s, 1H); 6.85 (dd, 1H); 7.02 (d, 1H)
90% In water; acetone; To a solution of <strong>[288385-99-9]3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene</strong> (11.36 g, 50 mmol) in acetone (200 ml) was added 4M aqueous ammonium acetate (700 ml) followed by a solution of titanium trichloride (15% in water, 340 ml) dropwise. The mixture was stirred for 10 minutes at ambient temperature and the mixture was extracted with ether. The organic layer was washed with 0.5N aqueous sodium hydroxide followed by water, brine, dried (MgSO4) and the volatiles were removed under vacuum. The residue was purified by column chromatography eluding with methylene chloride to give 4-fluoro-5-methoxy-2-methylindole (8.15 g, 90%). 1H NMR Spectrum: (DMSO) 2.35 (s, 3H); 3.8 (s, 3H); 6.1 (s, 1H); 6.85 (dd, 1H); 7.02 (d, 1H)
  • 4
  • [ 288385-96-6 ]
  • [ 288385-99-9 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogenchloride; sodium methylate; sodium; In tetrahydrofuran; methanol; A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5 C. The mixture was left to warm to ambient temperature and was stirred for 3 days. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1ml). The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added. The mixture was stirred for 1 hour at ambient temperature. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90%). MS-ESI: 250 [MNa]+ 1H NMR Spectrum: (CDCl3) 2.38 (s, 3H); 4.0 (s, 3H); 4.25 (s, 2H); 7.0 (dd, 1H); 8.05 (d, 1H)
90% With hydrogenchloride; sodium methylate; sodium; In tetrahydrofuran; methanol; A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5 C. The mixture was left to warm to ambient temperature and was stirred for 3 days. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1 ml). The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added. The mixture was stirred for 1 hour at ambient temperature. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90%). MS-ESI: 250 [MNa]+ 1H NMR Spectrum: (CDCl3) 2.38 (s, 3H); 4.0 (s, 3H); 4.25 (s, 2H); 7.0 (dd, 1H); 8.05 (d, 1H)
90% With hydrogenchloride; sodium methylate; sodium; In tetrahydrofuran; methanol; A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5 C. The mixture was left to warm to ambient temperature and was stirred for 3 days. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1 ml). The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added. The mixture was stirred for 1 hour at ambient temperature. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90%). MS-ESI: 250 [MNa]+ 1H NMR Spectrum: (CDCl3) 2.38 (s, 3H); 4.0 (s, 3H); 4.25 (s, 2H); 7.0 (dd, 1H); 8.05 (d, 1H)
  • 6
  • [ 67-56-1 ]
  • [ 121247-16-3 ]
  • [ 288385-99-9 ]
YieldReaction ConditionsOperation in experiment
Step 3: preparation of 1-(2-fluoro-3-methoxy-6-nitrophenyl)propan-2-one In a 100mL round-bottomed flask 2g 1-(2,3-difluoro-6-nitrophenyl)propan-2-one prepared from Step 2 was added to a solution of sodium methoxide in methanol(40mL), wherein the solution of sodium methoxide in methanol was prepared by slowly adding 2.27g Na to methanol with sitrring in an ice bath and stirring for 1h at 50C after the addition. The mixture was reacted for 1h at room temperature before the reaction was complete, and quenched by adding 1mL water and extracted with dichloromethane. The organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound. 1H NMR(400MHz,DMSO-d6) delta ppm:8.04-8.07(m,1H),7.31-7.35(m,1H),4.20-4.21(d, 2H),3.98(s,3H),2.28(s,3H).
  • 8
  • [ 288385-99-9 ]
  • [ 1609384-20-4 ]
  • 9
  • [ 288385-99-9 ]
  • [ 1609384-25-9 ]
  • 10
  • [ 288385-99-9 ]
  • 4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid ethyl ester [ No CAS ]
  • 11
  • [ 288385-99-9 ]
  • [ 1638768-25-8 ]
  • 12
  • [ 288385-99-9 ]
  • C17H13FN4O3 [ No CAS ]
  • 13
  • [ 288385-99-9 ]
  • [ 649735-41-1 ]
  • 14
  • [ 288385-99-9 ]
  • C17H15FN4O2 [ No CAS ]
  • 15
  • [ 288385-99-9 ]
  • [ 288385-88-6 ]
  • 16
  • [ 288385-99-9 ]
  • [ 952490-01-6 ]
  • 17
  • [ 288385-99-9 ]
  • [ 288385-93-3 ]
YieldReaction ConditionsOperation in experiment
With methanol; palladium on activated charcoal; at 20℃; for 36h; Step 4: preparation of 2-methyl-4-fluoro-5-methoxy-1H-indole In a 100mL round-bottomed flask 1.9g <strong>[288385-99-9]1-(2-fluoro-3-methoxy-6-nitrophenyl)propan-2-one</strong> prepared from Step 3 was added to 15mL methanol and dissolved, and 190mg palladium on carbon was added. The mixture was reacted for 36h at room temperature, then the reaction was stopped. The mixture was filtered, and concentrated to give the title compound. 1H NMR(400MHz,DMSO-d6) delta ppm: 11.01(br,1H),6.99-7.01(d,1H),6.853(m,1H), 6.10-6.11 (t,1H),3.79(s,3H),2.35(s,3H).
  • 18
  • [ 288385-99-9 ]
  • 1,2-dimethyl-4-fluoro-5-methoxy-1H-indole [ No CAS ]
Recommend Products
Same Skeleton Products

Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Halogenation of Phenols • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Nomenclature of Ethers • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reformatsky Reaction • Reimer-Tiemann Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction
Historical Records

Pharmaceutical Intermediates of
[ 288385-99-9 ]

Brivanib Alaninate Related Intermediates

Chemical Structure| 649736-31-2

[ 649736-31-2 ]

1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

Chemical Structure| 1142-20-7

[ 1142-20-7 ]

((Benzyloxy)carbonyl)-L-alanine

Chemical Structure| 51145-57-4

[ 51145-57-4 ]

Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate

Chemical Structure| 771-69-7

[ 771-69-7 ]

1,2,3-Trifluoro-4-nitrobenzene

Chemical Structure| 288385-88-6

[ 288385-88-6 ]

4-Fluoro-5-hydroxy-2-methylindole

Related Functional Groups of
[ 288385-99-9 ]

Fluorinated Building Blocks

Chemical Structure| 288385-98-8

[ 288385-98-8 ]

1-(3-(benzyloxy)-2-fluoro-6-nitrophenyl)propan-2-one

Similarity: 0.95

Chemical Structure| 649736-31-2

[ 649736-31-2 ]

1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

Similarity: 0.95

Chemical Structure| 454-16-0

[ 454-16-0 ]

1-Fluoro-2-methoxy-4-nitrobenzene

Similarity: 0.76

Chemical Structure| 864293-50-5

[ 864293-50-5 ]

4-Fluoro-5-methoxy-2-nitrobenzoic acid

Similarity: 0.76

Chemical Structure| 314298-13-0

[ 314298-13-0 ]

1-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

Similarity: 0.75

Aryls

Chemical Structure| 288385-98-8

[ 288385-98-8 ]

1-(3-(benzyloxy)-2-fluoro-6-nitrophenyl)propan-2-one

Similarity: 0.95

Chemical Structure| 649736-31-2

[ 649736-31-2 ]

1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

Similarity: 0.95

Chemical Structure| 454-16-0

[ 454-16-0 ]

1-Fluoro-2-methoxy-4-nitrobenzene

Similarity: 0.76

Chemical Structure| 864293-50-5

[ 864293-50-5 ]

4-Fluoro-5-methoxy-2-nitrobenzoic acid

Similarity: 0.76

Chemical Structure| 314298-13-0

[ 314298-13-0 ]

1-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

Similarity: 0.75

Ethers

Chemical Structure| 288385-98-8

[ 288385-98-8 ]

1-(3-(benzyloxy)-2-fluoro-6-nitrophenyl)propan-2-one

Similarity: 0.95

Chemical Structure| 454-16-0

[ 454-16-0 ]

1-Fluoro-2-methoxy-4-nitrobenzene

Similarity: 0.76

Chemical Structure| 864293-50-5

[ 864293-50-5 ]

4-Fluoro-5-methoxy-2-nitrobenzoic acid

Similarity: 0.76

Chemical Structure| 314298-13-0

[ 314298-13-0 ]

1-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

Similarity: 0.75

Chemical Structure| 1093656-34-8

[ 1093656-34-8 ]

2-Ethoxy-1-fluoro-4-nitrobenzene

Similarity: 0.74

Ketones

Chemical Structure| 288385-98-8

[ 288385-98-8 ]

1-(3-(benzyloxy)-2-fluoro-6-nitrophenyl)propan-2-one

Similarity: 0.95

Chemical Structure| 649736-31-2

[ 649736-31-2 ]

1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

Similarity: 0.95

Chemical Structure| 1214377-22-6

[ 1214377-22-6 ]

1-(2-Fluoro-6-nitrophenyl)ethanone

Similarity: 0.70

Chemical Structure| 113352-66-2

[ 113352-66-2 ]

1-(4-Methoxy-2-nitrophenyl)propan-2-one

Similarity: 0.70

Chemical Structure| 79110-05-7

[ 79110-05-7 ]

1-(2-Fluoro-5-nitrophenyl)ethanone

Similarity: 0.68

Nitroes

Chemical Structure| 288385-98-8

[ 288385-98-8 ]

1-(3-(benzyloxy)-2-fluoro-6-nitrophenyl)propan-2-one

Similarity: 0.95

Chemical Structure| 649736-31-2

[ 649736-31-2 ]

1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

Similarity: 0.95

Chemical Structure| 454-16-0

[ 454-16-0 ]

1-Fluoro-2-methoxy-4-nitrobenzene

Similarity: 0.76

Chemical Structure| 864293-50-5

[ 864293-50-5 ]

4-Fluoro-5-methoxy-2-nitrobenzoic acid

Similarity: 0.76

Chemical Structure| 314298-13-0

[ 314298-13-0 ]

1-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

Similarity: 0.75

; ;