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[ CAS No. 135306-45-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 135306-45-5
Chemical Structure| 135306-45-5
Chemical Structure| 135306-45-5
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Product Details of [ 135306-45-5 ]

CAS No. :135306-45-5 MDL No. :MFCD00061142
Formula : C9H8F2O Boiling Point : -
Linear Structure Formula :- InChI Key :FVDQWXARVQADKN-UHFFFAOYSA-N
M.W : 170.16 Pubchem ID :145620
Synonyms :

Calculated chemistry of [ 135306-45-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.36
TPSA : 17.07 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) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 2.28
Log Po/w (WLOGP) : 3.4
Log Po/w (MLOGP) : 2.94
Log Po/w (SILICOS-IT) : 3.33
Consensus Log Po/w : 2.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.57
Solubility : 0.459 mg/ml ; 0.0027 mol/l
Class : Soluble
Log S (Ali) : -2.28
Solubility : 0.902 mg/ml ; 0.0053 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.69
Solubility : 0.0347 mg/ml ; 0.000204 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.31

Safety of [ 135306-45-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 135306-45-5 ]

* 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 [ 135306-45-5 ]

[ 135306-45-5 ] Synthesis Path-Downstream   1~45

  • 1
  • [ 64248-63-1 ]
  • [ 925-90-6 ]
  • [ 135306-45-5 ]
YieldReaction ConditionsOperation in experiment
In aqueous hydrogen chloride; diethyl ether; EXAMPLE 1 (+-)-(2R*,3R*,5S*)-2-(3,5-Difluorophenyl)-3,5-dimethyl-2-morpholinol hydrochloride To a solution of 3,5-difluorobenzonitrile (Aldrich Chemical Co. Milwaukee. WI 53233)(50.0 g. 0.36 mole) in 500 mL of diethyl ether at 0 C. was added dropwise a solution of ethylmagnesium bromide (135 mL of a 3.OM solution 0.41 mole) in diethyl ether. The reaction mixture was refluxed for 3 hr. then chilled in an ice bath and hydrolyzed with 100 mL of 6N aqueous hydrogen chloride. The mixture was heated on a steam bath for 0.5 hr. The pH was adjusted to acid (litmus) and two phases were separated by extraction of the aqueous phase with diethyl ether. The combined extracts were dried (sodium sulfate) and concentrated in vacuo to give 61.3 g (91% of theory) of crude 3',5'-difluoropropiophenone.
  • 2
  • [ 135306-45-5 ]
  • [ 135306-46-6 ]
YieldReaction ConditionsOperation in experiment
99% With bromine; In dichloromethane; at 20℃;Inert atmosphere; Synthesis of 2-(tert-Butylamino)-<strong>[135306-45-5]3',5'-difluoropropiophenone</strong> (2m)Step 1. 2-Bromo-3t,5'-difluoropropiophenone (10m). To a solution of 3.00 g (0.018 mol) of <strong>[135306-45-5]3,5-difluoropropiophenone</strong>, 9m, in 70 mL of methylene chloride was added 10 drops of bromine. After stirring at room temperature under nitrogen for several minutes, the characteristic red color of bromine disappeared indicating initiation of the reaction. The remainder of the 0.9 mL (17.63 mmol) of bromine was added dropwise, and the reaction solution was allowed to stir at room temperature under nitrogen overnight. The reaction solution was quenched and brought to a pH of 9 with a saturated sodium bicarbonate solution. The product was extracted with methylene chloride, dried (Na2SO4), and filtered. The solvent was removed, and the resulting residue was dried briefly under high vacuum to give 4.36 g (99%) of 10m as a clear oil. 1H NMR (CDCl3) delta 7.57-7.49 (bdd, 2H), 7.09-7.01 (m, IH), 5.30-5.10 (q, IH), 1.91 (d, 3H).
With 1,4-dioxane dibromide; In 1,4-dioxane; EXAMPLE 2 (2S,3S,5R).2.(3,5.Difluorophenyl).3.5.dimethyl-2-morpholinol hydrochloride To <strong>[135306-45-5]3',5'-difluoropropiophenone</strong> (56.0 g. 0 33 mole) was added a solution of dioxane dibromide (81.8 g. 0.33 mole) in dioxane (500 ml) The reaction mixture was worked up as in Example 1 to yield crude 2-bromo-<strong>[135306-45-5]3',5'-difluoropropiophenone</strong> (83.9 g).
  • 4
  • [ 104-88-1 ]
  • [ 135306-45-5 ]
  • 4-Chloro-benzoic acid (1S,2S,3S)-1-(4-chloro-phenyl)-3-(3,5-difluoro-phenyl)-3-hydroxy-2-methyl-propyl ester [ No CAS ]
  • 4-Chloro-benzoic acid (1R,2R,3R)-1-(4-chloro-phenyl)-3-(3,5-difluoro-phenyl)-3-hydroxy-2-methyl-propyl ester [ No CAS ]
  • 5
  • [ 616-34-2 ]
  • [ 135306-45-5 ]
  • [1-(3,5-difluoro-phenyl)-propylamino]-acetic acid methyl ester [ No CAS ]
  • 6
  • [ 135306-45-5 ]
  • 1-(3,5-difluoro-phenyl)-propan-1-one oxime [ No CAS ]
  • 7
  • [ 135306-45-5 ]
  • 1-(3,5-difluoro-phenyl)-propylamine [ No CAS ]
  • 8
  • [ 135306-45-5 ]
  • [ 847448-12-8 ]
  • 9
  • [ 135306-45-5 ]
  • 3-[1-(3,5-difluoro-phenyl)-propyl]-2-mercapto-3<i>H</i>-imidazole-4-carboxylic acid methyl ester [ No CAS ]
  • 10
  • [ 135306-45-5 ]
  • Sodium; (E)-2-[1-(3,5-difluoro-phenyl)-propyl]-formyl-amino}-2-methoxycarbonyl-ethenolate [ No CAS ]
  • 11
  • [ 135306-45-5 ]
  • (1S,2R,3S)-1-(4-chlorophenyl)-3-(3,5-difluorophenyl)-2-methylpropane-1,3-diol [ No CAS ]
  • 12
  • [ 135306-45-5 ]
  • 1-(3,5-Difluoro-phenyl)-2-(2-hydroxy-1-methyl-ethylamino)-propan-1-one [ No CAS ]
  • 13
  • [ 135306-45-5 ]
  • hydrobromide salt of (2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethyl-2-morpholinol [ No CAS ]
  • 14
  • [ 135306-45-5 ]
  • 1-(3,5-Difluoro-phenyl)-propylidene-hydrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium chloride; In methanol; water; Preparation 1 1-(3,5-Difluoro-phenyl)-propylidene-hydrazine To a stirring solution of <strong>[135306-45-5]1-(3,5-Difluoro-phenyl)-propan-1-one</strong> (5.00 g, 29.40 mmol) in 5.0 mL of CH3OH was added a solution of hydrazone (35% in H2O, 42.00 mL, 29.40 mmol). The mixture was then heated to 75 C. for 1 h, cooled to ambient temperature, and poured into equal amounts of CH2Cl2 and H2O. The organic layer was then collected and washed with a saturated solution of NaCl. The organic layer was then dried over MgSO4, and concentrated under reduced pressure to yield an 8:1 mixture of hydrazone isomers (5.53 g, >95%) as yellow oil. (Major isomer) 400 MHz 1H NMR (CDCl3) delta7.11-7.16 (m, 2H), 6.65-6.71 (m, 1H), 5.52 (br s, 2H), 2.53 (q, J=7.88, 2H), 1.18 (t, J=7.05, 3H).
  • 15
  • [ 135306-45-5 ]
  • (+/-)-(2R*,3R*,5S*)-2-(3,5-difluorophenyl)-3,5-dimethyl-2-morpholinol hydrochloride [ No CAS ]
  • [ 135306-46-6 ]
YieldReaction ConditionsOperation in experiment
With 1,4-dioxane dibromide; bromine; In 1,4-dioxane; water; A solution of dioxane dibromide, prepared by the dropwise addition of bromine (52.7 g. 0.33 mole) to 500 mL of dioxane. was added dropwise to a solution of <strong>[135306-45-5]3',5'-difluoropropiophenone</strong> (56.0 g. 0.33 mole) in 500 mL of dioxane. After stirring at room temperature overnight the reaction mixture was poured into 2.5 L of water The aqueous solution was extracted with dichloromethane. The extracts were dried (sodium sulfate). and concentrated in vacuo to give crude 2.bromo.3', 5'-difluoropropiophenone. After distillation on a Kugelrohr a a boiling point of 60-62 C. and 0.3 mm Hg, the product 2.bromo.3',5' -difluoropropiophenone had a refractive index eta21.1* =1.5273. Elemental Analysis: Calcd. for C9 H7 BrF2 O (m.w. 249.06): C, 43.40%; H, 2.83%. Found: C, 43.53%; H, 2.88%. NMR-1 H: (DMSO-d6) delta1.91 (d, 3H. CH3)5.14 (q. lH, CH), 7.02-7 55 (aromatic H's).
  • 16
  • [ 107-21-1 ]
  • [ 135306-45-5 ]
  • [ 932705-87-8 ]
  • 17
  • [ 932705-71-0 ]
  • [ 135306-45-5 ]
  • [ 1187306-69-9 ]
  • 18
  • [ 135306-45-5 ]
  • (R)-(+)-1-(3,5-difluorophenyl)-2-hydroxypropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With oxygen; trifluoroacetic acid; copper dichloride; In tetrahydrofuran; water; at 20℃; General procedure: The reaction was carried out in a two-necked round bottom flask (100 mL) fitted with a magnetic stir bar, rubber septum and a balloon to hold the oxygen. To the flask was added CuCl2 (2.72 g, 20.0 mmol), chiral bimetallic palladium (II) complex B (0.065 g, 0.05 mmol), and an aqueous solution of THF (40 mL, THF /water 8:2) or an aqueous solution of 1,4-dioxane (1,4-dioxane/water 6:4). The mixture was degassed with O2 by admitting the O2 and removing it under vacuum, and the flask was them placed under positive pressure of oxygen. A solution of the requisite ketone (10.0 mmol) in THF (2 mL) was injected in the solution followed by trifluoroacetic acid (0.1 mL). The reaction mixture was stirred at room temperature and the progress of the reaction was monitored by TLC. When the conversion of the starting ketone was judged to be >90% complete (24-30 hr), the mixture was diluted with water and extracted with ether (2 x 15 mL). The combined ether layers were washed with a solution of sodium bicarbonate and water. The ether layer dried over Na2SO4 and concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (100-200 mesh).
  • 19
  • [ 135306-45-5 ]
  • [ 1392440-71-9 ]
  • 20
  • [ 135306-45-5 ]
  • [ 1392440-72-0 ]
  • 21
  • [ 135306-45-5 ]
  • [ 1392440-73-1 ]
  • 22
  • [ 135306-45-5 ]
  • [ 73183-34-3 ]
  • C15H19BF2O3 [ No CAS ]
  • 23
  • [ 554-14-3 ]
  • [ 135306-45-5 ]
  • [ 1440663-89-7 ]
YieldReaction ConditionsOperation in experiment
68% With silver (II) carbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; lithium acetate; palladium diacetate; tricyclohexylphosphine; In 1,2-dimethoxyethane; at 100℃; for 24.0h;Schlenk technique; Inert atmosphere; General procedure: In a glove box, a 25 mL of Schlenk tube equipped with a stir bar was charged with Pd(OAc)2 (0.03 mmol, 0.1 equiv), PCy3 (0.03 or 0.06 mmol, 0.1 or 0.2 equiv), LiOAc (0.45 mmol, 1.5 equiv) (or NaOAc), TEMPO (0.12 mmol, 0.4 equiv), Ag2CO3 (0.9 mmol, 3 equiv). The tube was fitted with a rubber septum and removed out of the glove box. DME (2 mL), propiophenone (0.9 mmol, 3.0 equiv) and thiophene (0.3 mmol, 1.0 equiv) were added in turn to the Schlenk tube through the rubber septum using syringes, and then the septum was replaced with a Teflon screwcap under nitrogen flow (if the thiophene or the substituted propiophenone was solid, it was added to the tube in the glove box). The reaction mixture was stirred at 100 oC or 120 oC for 24 h. After cooling down, the reaction mixture was diluted with 10 mL of ethyl ether, filtered through a pad of silica gel, followed by washing the pad of the silica gel with the same solvent (20 mL), concentrated under reduced pressure. The residue was then purified by flash chromatography on silica gel with 2-15 % ethyl ether in petroleum ether as eluent to provide the corresponding product.
  • 24
  • [ 135306-45-5 ]
  • [ 1428228-52-7 ]
  • 25
  • [ 135306-45-5 ]
  • [ 1428229-06-4 ]
  • 26
  • [ 95-92-1 ]
  • [ 135306-45-5 ]
  • [ 1428228-99-2 ]
  • 27
  • [ 5332-24-1 ]
  • [ 135306-45-5 ]
  • 1-(3,5-difluoro-4-quinolin-3-ylphenyl)propan-1-one [ No CAS ]
  • 1-(3,5-difluorophenyl)-2-quinolin-3-ylpropan-1-one [ No CAS ]
  • 28
  • [ 135306-45-5 ]
  • [ 94972-95-9 ]
  • (E)-4-(1-(4-(benzyloxy)phenyl)-2-(3,5-difluorophenyl)but-1-en-1-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.8% With titanium tetrachloride; zinc; In tetrahydrofuran; at 0℃; for 5.0h;Inert atmosphere; Reflux; Step-1: Synthesis of (E)-4-(l-(4-(benz loxy)phenyl)-2-(3,5-difluorophenyl)but-l-en-l- yl)phenol Zinc dust (5.2 g, 78.6 mmol) was suspended in dry THF (50 mL) and cooled this suspension to -10 C. To this TiCl4 (4.4 mL, 39.3 mmol) was added slowly under nitrogen atmosphere, stirred there for 15 min, slowly allowed it to reach room temperature and heated to reflux for 2 h. The resulting mixture was cooled to 0 C, and a solution of 4-(benzyloxy) phenyl)(4- hydroxyphenyl) methanone (4 g, 13.1 mmol) and l-(3,5-difluorophenyl)propan-l-one (2.35 g, 13.8 mmol) in dry THF (80 mL) were added and the contents were refluxed for 5 h. The reaction mixture was cooled to room temperature and quenched with 10% aqueous K2C03 solution and was extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate and concentrated. The crude material was purified by column chromatography over 230-400 mesh silica using (2:8) ethyl acetate in n- hexane to afford (E)-4-(l-(4-(benzyloxy)phenyl)-2-(3,5-difluorophenyl)but-l-en-l-yl)phenol (4.05 g, 69.8 %).
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; diethyl ether; at -70 - 20℃; for 3.0h; General procedure: At -70 C., intermediate 36 (5.4 g, 20.6 mmoles) in solution in THF (75 mL) is treated with a solution of methylmagnesium bromide (3 M in diethyl ether) (8.1 mL, 24 mmoles). The mixture is stirred with return to ambient temperature for 3 hours before being poured into a 1N aqueous HCl solution at 0 C. The product is extracted with AcOEt, and the organic phase is washed with a saturated aqueous NaCl solution, dried over MgSO4 and then concentrated in vacuo. Intermediate 37 is obtained in the form of a solid (3.6 g).
  • 30
  • [ 271-58-9 ]
  • [ 135306-45-5 ]
  • (3,5-difluorophenyl)(quinolin-3-yl)methanone [ No CAS ]
  • 31
  • [ 87-48-9 ]
  • [ 135306-45-5 ]
  • 6-bromo-2-(3,5-difluorophenyl)-3-methylquinoline-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In ethanol; water; at 180℃; for 0.333333h;Microwave irradiation; 300 mg (1.33 mmol) of 5-bromo-1H-indole-2,3-dione were initially charged in 2 ml of 20% strength aqueous ethanol solution, and 565 mg (3.31 mmol) of <strong>[135306-45-5]1-(3,5-difluorophenyl)propan-1-one</strong> and 238 mg (4.25 mmol) of potassium hydroxide were added. The reaction mixture was then heated in the microwave (Biotage) at 180 C. for 20 min. After cooling to RT, the mixture was added to 100 ml of 1 M hydrochloric acid. The precipitated solid was then filtered off, washed with water and dried under reduced pressure. This gave 490 mg (69% of theory, purity 71%) of the title compound. LC/MS (Method 1, ESIpos): Rt=1.01 min, m/z=378/380 [M+H]+.
  • 32
  • [ 135306-45-5 ]
  • methyl 4-([6-bromo-2-(3,5-difluorophenyl)-3-methylquinolin-4-yl]carbonyl}amino)bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]
  • 33
  • [ 135306-45-5 ]
  • 4-([6-bromo-2-(3,5-difluorophenyl)-3-methylquinolin-4-yl]carbonyl}amino)bicyclo[2.2.2]octane-1-carboxylic acid [ No CAS ]
  • 34
  • [ 135306-45-5 ]
  • [ 640-61-9 ]
  • (E)-N-(3-(3,5-difluorophenyl)-3-oxoprop-1-en-1-yl)-N,4-dimethylbenzenesulfonamide [ No CAS ]
  • 35
  • [ 455-40-3 ]
  • [ 135306-45-5 ]
  • 36
  • [ 874889-34-6 ]
  • [ 2386-64-3 ]
  • [ 135306-45-5 ]
YieldReaction ConditionsOperation in experiment
94% In tetrahydrofuran; at 0 - 20℃; for 2.0h; 3,5-Difluoro-N-methoxy-N-methylbenzamide 11b (1.0 g, 4.98 mmol) was dissolved in 20 mL of dry tetrahydrofuran, and ethylmagnesium chloride reagent (10 mL, 10 mmol, 1 M / THF), reacted at room temperature for 2 hours. The reaction was quenched by the addition of 20 mL of a saturated ammonium chloride solution. Extracted with ethyl acetate (50 mL × 3), (796 mg, colorless oil), yield: 94%.
  • 37
  • [ 129714-97-2 ]
  • [ 135306-45-5 ]
  • 38
  • [ 135306-45-5 ]
  • 1-(3,5-difluorophenyl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With methanol; sodium tetrahydroborate; at 0 - 20℃; for 5.0h; 1-(3,5-Difluorophenyl)propan-1-one 11c (796 mg, 4.68 mmol) was dissolved in 10 mL of methanol, slowly at 0 CSodium borohydride (531 mg, 14.0 mmol) was added, and the mixture was added and reacted at room temperature for 5 hours. Concentrated under reduced pressure, the residue obtained was silica gelPurification by column chromatography (eluent: A) to give 1-(3,5-difluorophenyl)propan-1-ol 11d (732 mg, white solid)Rate: 91%.
  • 39
  • [ 135306-45-5 ]
  • 1-(3,5-difluorophenyl)propyl methanesulfonate [ No CAS ]
  • 40
  • [ 135306-45-5 ]
  • 5-cyclopropyl-4-(((7-(1-(3,5-difluorophenyl)propyl)-7-azaspiro[3.5]fluoren-2-yl)methoxy)Methyl)-2-fluoro-N-(methylsulfonyl)benzamide [ No CAS ]
  • 41
  • [ 135306-45-5 ]
  • 5-cyclopropyl-4-(((1-(1-(3,5-difluorophenyl)propyl)-4-fluoropiperidin-4-yl)methoxy)methyl)-2-fluorine-N-(methylsulfonyl)benzamide [ No CAS ]
  • 42
  • [ 135306-45-5 ]
  • 1-(1-chloropropyl)-3,5-difluorobenzene [ No CAS ]
  • 43
  • [ 135306-45-5 ]
  • methyl 5-cyclopropyl-4-(((1-(1-(3,5-difluorophenyl)propyl)-3-fluoroazetidin-3-yl)methoxy)methyl)-2-fluorobenzoate [ No CAS ]
  • 44
  • [ 135306-45-5 ]
  • C24H25F4NO3 [ No CAS ]
  • 45
  • [ 135306-45-5 ]
  • 5-cyclopropyl-4-(((1-(1-(3,5-difluorophenyl)propyl)-3-fluoroazetidin-3-yl)methoxy)methyl)-2-fluoro-N-(methylsulfonyl)benzamide [ No CAS ]
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