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[ CAS No. 477312-25-7 ]

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3d Animation Molecule Structure of 477312-25-7
Chemical Structure| 477312-25-7
Chemical Structure| 477312-25-7
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Product Details of [ 477312-25-7 ]

CAS No. :477312-25-7 MDL No. :MFCD16617621
Formula : C9H10F3NO Boiling Point : -
Linear Structure Formula :- InChI Key :XRRKIDIISISOKH-UHFFFAOYSA-N
M.W :205.17 Pubchem ID :22605542
Synonyms :

Calculated chemistry of [ 477312-25-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.61
TPSA : 35.25 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 3.54
Log Po/w (MLOGP) : 1.98
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 2.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.393 mg/ml ; 0.00191 mol/l
Class : Soluble
Log S (Ali) : -2.74
Solubility : 0.373 mg/ml ; 0.00182 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.11
Solubility : 0.16 mg/ml ; 0.000782 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 477312-25-7 ]

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

Application In Synthesis of [ 477312-25-7 ]

* 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 [ 477312-25-7 ]

[ 477312-25-7 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 85013-98-5 ]
  • [ 477312-25-7 ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; sodium cyanoborohydride; In methanol; at 120℃; for 0.0833333h; An Emrys Process Vial (2-5 ml) was charged with 420 mg (2 mmol) of 1-(4- trifluoromethoxy-phenyl)-ethanone, ammonium acetate in MeOH (4.0 ml of a 5 M solution, 20 mmol) and sodium cyanoborohydride in MeOH (0.440 ml of a 5 M solution, 2.2 mmol). The reaction vessel was sealed and heated to 120°C for 5 min in an Emrys Optimizer. After cooling and manual release of remaining pressure the vessel was uncapped and the reaction mixture concentrated at reduced pressure. The residue was dissolved in Et20 (10 ml) and extracted with 2 M aqueous HCI (3 x 5 ml). The combined aqueous phases were adjusted to pH 9 with a 10 M aqueous KOH and extracted with CH2C12 (4 x 10 ml). The combined organic phases were dried over MgS04 and the solvent evaporated at reduced pressure to afford 1-(3- trifluoromethoxy-phenyl)-ethyl amine which is used as crude product for step 2.
  • 2
  • ethylene dichloride hydrochloride [ No CAS ]
  • [ 477312-25-7 ]
  • [ 54495-51-1 ]
  • [ 477308-96-6 ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine; In dichloromethane; Example 218 Preparation of (+-)-3-Pyridin-2-yl-N-[1-(3-trifluoromethoxyphenyl)-ethyl]acrylamide To a solution of 3-(pyridin-2-yl)acrylic acid, Preparation 16 (50 mg) in CH2Cl2 (2 mL) at room temperature were added (+-)-1-(3-trifluoromethoxy phenyl)ethylamine, Preparation 15 (76 mg), EDC hydrochloride (129 mg), DMAP (41 mg), and triethylamine (0.2 mL), and the resulting solution was stirred at room temperature for 12 hours. The crude product was purified by silica gel chromatography eluding with ethyl acetate to provide the title compound as the racemate (96 mg). This racemate was separated by HPLC using AD column eluding with hexanes/ethanol (9:1) to give the title compound as an enantiomer of undetermined chirality. 1H NMR (CDCl3, 300 mHz) δ: 1.55 (3H, d, J=6.9 Hz), 5.28 (1H, quintet, J=7.1 Hz), 6.08 (1H, d, J=7.6 Hz), 7.02 (1H, d, J=15.1 Hz), 7.10-7.45 (6H, m), 7.62 (1H, d, J=15.1 Hz), 7.69 (1H, m), 8.59 (1H, d, J=4.4 Hz). MS: 337 [M+H]+
  • 3
  • 2-phenyl-4-trifluoromethyl-thiazole-5-carboxylic acid [ No CAS ]
  • [ 477312-25-7 ]
  • 2-phenyl-4-trifluoromethyl-thiazole-5-carboxylic acid [1-(3-trifluoromethoxyphenyl)-ethyl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% 2-Phenyl-4-trifluoromethyl-thiazole-5-carboxylic acid [1-(3-trifluoromethoxyphenyl)-ethyl]-amide. To a solution of 2-phenyl-4-trifluoromethyl-thiazole-5-carboxylic acid (35 mg, 0.128 mmol) in DMF (1 mL) was added PyBOP (73 mg, 0.141 mmol) and DMAP (16 mg, 0.128 mmol). A solution of 1-(3-trifluoromethoxyphenyl)-ethylamine (27 mg, 0.128 mmol) in DMF (0.5 mL) was then added, followed by Et3N (36 μL, 0.256 mmol). This mixture was stirred at 25 C. for 18 h. The reaction mixture was applied directly to a preparatory HPLC column for purification (C18, 10-100% methanol/water/0.1% trifluoroacetic acid) which gave the amide as a white solid (24.9 mg, 42%).
  • 4
  • [ 477312-25-7 ]
  • [ 1514568-53-6 ]
  • [ 1610853-10-5 ]
YieldReaction ConditionsOperation in experiment
58% f) Synthesis of 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-N-[1-[3-(trifluoromethyloxy)-phenyl]-ethyl]-thiazole-5-carboxylic acid amide To a stirred solution of 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-thiazole-5-carboxylic acid (0.15 g, 0.53 mmol) in dimethylformamide (3 ml) are added N-methylmorpholine (0.12 ml, 1.06 mmol), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (0.25 g, 0.79 mmol) at 0 C. The reaction mixture is stirred at 0 C. for 5 min before <strong>[477312-25-7]1-[3-(trifluoromethyloxy)-phenyl]-ethyl-amine</strong> (0.13 g, 0.63 mmol) is added. The reaction mixture is then stirred at RT for 16 h. After completion of the reaction, the reaction mixture is diluted with EtOAc (10 ml). The organic layer is washed with saturated sodium hydrogen carbonate solution (15 ml), saturated ammonium chloride solution (15 ml), water (20 ml), and brine (20 ml), dried over sodium sulfate and evaporated to dryness to get the crude product, which is purified by column chromatography (silica gel, 5% acetone/hexane) followed by crystallization from acetone/pentane affording 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-N-[1-[3-(trifluoromethyloxy)-phenyl]-ethyl]-thiazole-5-carboxylic acid amide (example 9) (0.15 g, 0.31 mmol, 58%). [M+H]+ 472.2.
58% To a stirred solution of 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-thiazole-5-carboxylic acid (0.15g, 0.53 mmol) in dimethylformamide (3 ml) are added N-methylmorpholine (0.12 ml, 1.06 mmol), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (0.25 g, 0.79 mmol) at 0 C. The reaction mixture is stirred at 0 C for 5 min before 1 -[3 -(trifluoromethyloxy)-phenyl]-ethyl-amine (0.13 g,0.63 mmol) is added. The reaction mixture is then stirred at RT for 16 h. After completion of the reaction, the reaction mixture is diluted with EtOAc (10 ml). The organic layer is washed with saturated sodiumhydrogen carbonate solution (15 ml), saturated ammonium chloride solution (15 ml), water ( 2 0 ml), and brine ( 2 0 ml), dried over sodium sulfate and evaporated to dryness to get the crude product, which is purified by column chromatography (silica gel, 5% acetone/ hexane) followed by crystallization fromacetone/pentane affording 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-N-[1 -[3-(trifluoromethyloxy)-phenyl]-ethyl]-thiazole-5-carboxylic acid amide (exam ple 9) (0.15 g, 0.31 mmol,58%). [M+H]+ 472.2.
  • 5
  • [ 477312-25-7 ]
  • 1-(2-methylpyridin-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-amine [ No CAS ]
  • [ 530-62-1 ]
  • 1-(1-(2-methylpyridin-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-3-(1-(3-(trifluoromethoxy)phenyl)ethyl)urea trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
A solution of l-(2-methylpyridin-4-yl)-lH-pyrazolo[3,4-c]pyridin-5-amine (25 mg, 0.11 mmol) in dioxane (1 mL) was treated with imidazole (40 mg, 0.59 mmol) and carbonyl diimidazole (100 mg, 0.62 mmol). The mixture was stirred for 3 hours. An aliquot was treated with methanol, and the presence of the corresponding methyl carbamate as observed by LC/MS was used to indicate consumption of the aminopyridine. Next, l-(3- (0738) (trifluoromethoxy)phenyl)ethanamine (110 mg, 0.54 mmol) was added followed by TEA (0.10 mL, 0.72 mmol) and the mixture stirred for 2 hours, then concentrated to dryness. The residue was dissolved in DMSO and purified by reverse phase chromatography (MeCN/water with 0.1% TFA). The LC fractions were lyophilized to provide the TFA salt of l-(l-(2-methylpyridin-4-yl)- lH-pyrazolo[3,4-c]pyridin-5-yl)-3-(l-(3-(trifluoromethoxy)-phenyl)ethyl)urea: MS (EI) calc'd for C22H2oF3N602 [M+H]+ 457, found 457; 1H NMR (600 MHz, OMSO-d6) δ 9.40 (s, 1 H), 9.24 (s, 1 H), 8.70 (d, J= 6.5 Hz, 1 H), 8.68 (s, 1 H), 8.16 (s, 1 H), 8.14 (s, 1 H), 8.11 (d, J= 5.6 Hz, 1 H), 7.52 (d, J= 6.4 Hz, 1 H), 7.46 (t, J= 7.9 Hz, 1 H), 7.38 (d, J= 7.9 Hz, 1 H), 7.29 (s, 1 H), 7.21 (d, J= 7.6 Hz, 1 H), 4.91 (dt, J= 7.1 Hz, 1 H), 2.70 (s, 3 H), 1.40 (d, J= 7.1 Hz, 3 H)
  • 6
  • [ 477312-25-7 ]
  • 5-(2-aminobenzo[d]thiazol-6-yl)-2-methoxynicotinic acid [ No CAS ]
  • 5-(2-aminobenzo[d]thiazol-6-yl)-2-methoxy-N-(1-(3-(trifluoromethoxy)phenyl)ethyl)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; Step 2: 5-(2-Aminobenzo[d]thiazol-6-yl)-2-methoxynicotinic acid (225mg, 0.4762mmol) and 15mL of N,N-dimethylformamide were added to a 50mL round-bottomed flask. Next, 1-(3-(trifluoromethoxy)phenyl)ethyl-1-amine (146.54mg, 0.7143mmol), triethylamine (480mg, 4.672mmol), and BOP reagent (330mg, 0.7467mmol) were added sequentially. The reaction was carried out overnight at room temperature under the protection of nitrogen gas. 80mL of ethyl acetate was added to the system. The resultant mixture was washed with saturated brine for 5 times (50mL*5). The organic phase of ethyl acetate was dried over anhydrous sodium sulfate and filtered, and the filtrate was spin-dried to give 5-(2-aminobenzo[d]thiazol-6-yl)-2-methoxy-N-(1-(3-(trifluoromethoxy)phenyl)ethyl) nicotinamide Z3 (40mg, Y:17%). ES-API:[M+H]+=489.1. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (d, J = 7.9 Hz, 1H), 8.55 (d, J = 2.5 Hz, 1H), 8.15 (d, J = 2.5 Hz, 1H), 7.99 (d, J= 1.8 Hz, 1H), 7.61 - 7.33 (m, 7H), 7.21 (d, J = 7.2 Hz, 1H), 5.16 (p, J = 7.0 Hz, 1H), 3.97 (s, 3H), 1.44 (d, J = 7.0 Hz, 3H).
40 mg With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; 5-(2-Aminobenzo[d]thiazol-6-yl)-2-methoxynicotinic acid (225mg, 0.4762mmol) and 15mL of N,N-dimethylformamide were added to a 50mL round-bottomed flask. Next, 1-(3-(trifluoromethoxy)phenyl)ethyl-1-amine (146.54mg, 0.7143mmol), triethylamine (480mg, 4.672mmol), and BOP reagent (330mg, 0.7467mmol) were added sequentially. The reaction was carried out overnight at room temperature under the protection of nitrogen gas. 80mL of ethyl acetate was added to the system. The resultant mixture was washed with saturated brine for 5 times (50mL*5). The organic phase of ethyl acetate was dried over anhydrous sodium sulfate and filtered, and the filtrate was spin-dried to give 5-(2-aminobenzo[d]thiazol-6-yl)-2-methoxy-N-(1-(3-(trifluoromethoxy)phenyl)ethyl) nicotinamide Z3 (40mg, Y:17%). ES-API:[M+H]+=489.1. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (d, J = 7.9 Hz, 1H), 8.55 (d, J = 2.5 Hz, 1H), 8.15 (d, J = 2.5 Hz, 1H), 7.99 (d, J= 1.8 Hz, 1H), 7.61 - 7.33 (m, 7H), 7.21 (d, J = 7.2 Hz, 1H), 5.16 (p, J = 7.0 Hz, 1H), 3.97 (s, 3H), 1.44 (d, J = 7.0 Hz, 3H).
40 mg With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; 5-(2-Aminobenzo[d]thiazol-6-yl)-2-methoxynicotinic acid (225mg, 0.4762mmol) and 15mL of N,N-dimethylformamide were added to a 50mL round-bottomed flask. Next, 1-(3-(trifluoromethoxy)phenyl)ethyl-1-amine (146.54mg, 0.7143mmol), triethylamine (480mg, 4.672mmol), and BOP reagent (330mg, 0.7467mmol) were added sequentially. The reaction was carried out overnight at room temperature under the protection of nitrogen gas. 80mL of ethyl acetate was added to the system. The resultant mixture was washed with saturated brine for 5 times (50mL*5). The organic phase of ethyl acetate was dried over anhydrous sodium sulfate and filtered, and the filtrate was spin-dried to give 5-(2-aminobenzo[d]thiazol-6-yl)-2-methoxy-N-(1-(3-(trifluoromethoxy)phenyl)ethyl) nicotinamide Z3 (40mg, Y:17%). ES-API:[M+H]+=489.1. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (d, J = 7.9 Hz, 1H), 8.55 (d, J = 2.5 Hz, 1H), 8.15 (d, J = 2.5 Hz, 1H), 7.99 (d, J= 1.8 Hz, 1H), 7.61 - 7.33 (m, 7H), 7.21 (d, J = 7.2 Hz, 1H), 5.16 (p, J = 7.0 Hz, 1H), 3.97 (s, 3H), 1.44 (d, J = 7.0 Hz, 3H).
40 mg With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; 5-(2-Aminobenzo[d]thiazol-6-yl)-2-methoxynicotinic acid (225mg, 0.4762mmol) and 15mL of N,N-dimethylformamide were added to a 50mL round-bottomed flask. Next, 1-(3-(trifluoromethoxy)phenyl)ethyl-1-amine (146.54mg, 0.7143mmol), triethylamine (480mg, 4.672mmol), and BOP reagent (330mg, 0.7467mmol) were added sequentially. The reaction was carried out overnight at room temperature under the protection of nitrogen gas. 80mL of ethyl acetate was added to the system. The resultant mixture was washed with saturated brine for 5 times (50mL*5). The organic phase of ethyl acetate was dried over anhydrous sodium sulfate and filtered, and the filtrate was spin-dried to give 5-(2-aminobenzo[d]thiazol-6-yl)-2-methoxy-N-(1-(3-(trifluoromethoxy)phenyl)ethyl) nicotinamide Z3 (40mg, Y:17%). ES-API:[M+H]+=489.1. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (d, J = 7.9 Hz, 1H), 8.55 (d, J = 2.5 Hz, 1H), 8.15 (d, J = 2.5 Hz, 1H), 7.99 (d, J= 1.8 Hz, 1H), 7.61 - 7.33 (m, 7H), 7.21 (d, J = 7.2 Hz, 1H), 5.16 (p, J = 7.0 Hz, 1H), 3.97 (s, 3H), 1.44 (d, J = 7.0 Hz, 3H).

  • 7
  • [ 477312-25-7 ]
  • [ 22287-35-0 ]
  • [ 530-62-1 ]
  • 1-bicyclo[1.1.1]pent-1-yl-3-[1-(3-trifluoromethoxyphenyl)ethyl]urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of bicyclo[1.1.1]pentan-1-amine hydrochloride (12 mg, 0.1 mmol, 1 eq) in MeCN (0.5 mL), DIPEA (34 μL, 0.2 mmol, 2 eq) and CDI (16 mg, 0.1 mmol, 1 eq) were added in sequence. The mixture was stirred at 60 C for 1 hour. A solution of 1-(3- (trifluoromethoxy)phenyl)ethanamine (21 mg, 0.1 mmol, 1 eq) in MeCN (0.4 mL) and H2O (0.1 mL) was added. The reaction mixture was further stirred at 60 C overnight. The mixture was allowed to cool to rt and purified by prep. HPLC (column: Waters XBridge, 30x75 mm, 10 um, UV/MS, basic conditions). LC-MS (1): tR = 1.11min; [M+H]+: 315.2.
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