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[ CAS No. 771583-81-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 771583-81-4
Chemical Structure| 771583-81-4
Chemical Structure| 771583-81-4
Structure of 771583-81-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 771583-81-4 ]

CAS No. :771583-81-4 MDL No. :MFCD06213291
Formula : C8H7ClF3N Boiling Point : -
Linear Structure Formula :- InChI Key :VPKIGWHSTBKRTA-UHFFFAOYSA-N
M.W : 209.60 Pubchem ID :17750830
Synonyms :

Calculated chemistry of [ 771583-81-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.13
TPSA : 26.02 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.04
Log Po/w (XLOGP3) : 2.29
Log Po/w (WLOGP) : 3.82
Log Po/w (MLOGP) : 3.17
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 2.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.79
Solubility : 0.339 mg/ml ; 0.00162 mol/l
Class : Soluble
Log S (Ali) : -2.47
Solubility : 0.704 mg/ml ; 0.00336 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.95
Solubility : 0.0234 mg/ml ; 0.000112 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 771583-81-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 771583-81-4 ]

* 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 [ 771583-81-4 ]

[ 771583-81-4 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 771583-81-4 ]
  • [ 1241828-40-9 ]
  • [ 1241827-62-2 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25℃; for 16h; Example 90: N-(4-chloro-2-(trifiuoromethyl)benzyl)-2-(2-cyanoethyl)-3-oxo-2,3- dihydro-[l,2,4]triazolo[4,3-a]pyridine-6-carboxamide; [0288] To a 8 mL vial fitted with a teflon cap was added 2-(2-cyanoethyl)-3-oxo-2,3-dihydro- [l,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid (100 mg, 0.431 mmol) and IH- benzo[d][l,2,3]triazol-l-ol (61.1 mg, 0.452 mmol), DMF (Volume: 2.0 ml), Nl- ((ethylimino)methylene)-N3,N3-dimethylpropane-l,3-diamine hydrochloride (87 mg, 0.452 mmol) and <strong>[771583-81-4](4-chloro-2-(trifluoromethyl)phenyl)methanamine</strong> (91 mg, 0.435 mmol) and the reaction mixture was allowed to stir at 250C for 16h. Reaction was diluted with 15mL water to give a solid. The solid product was filtered and dried by suction. Solid product was added into 1OmL 30% isopropanol in water, broke up with a spatula, sonicated, and then heated to 650C. An additional 3mL isopropanol was added and again the solid was broken up with a spatula, the mixture was sonicated, then heated to 650C to give a suspension which was allowed to cool to room temperature. The solid was collected by filtration, washed with 1OmL 30% isopropanol in water and dried by suction to give 77.6 mg of the title compound. 1H NMR (DMSO-^, 400 MHz) delta: 9.28 (t, J = 5.7 Hz, IH), 8.61-8.65 (m, IH), 7.81 (d, J = 2.3 Hz, IH), 7.76 (dd, J = 8.5, 2.1 Hz, IH), 7.57-7.66 (m, 2H), 7.35 (dd, J = 9.7, 1.1 Hz, IH), 4.60 (d, J = 5.3 Hz, 2H), 4.20 (t, J = 6.3 Hz, 2H), 3.04 (t, J = 6.3 Hz, 2H). [M+H] calc'd for Ci8Hi3ClF3N5O2, 424; Found, 424.
  • 2
  • [ 771583-81-4 ]
  • [ 32315-10-9 ]
  • [ 1338065-54-5 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; at 0 - 80℃; Commercially available <strong>[771583-81-4]4-chloro-2-trifluoromethylbenzylamine</strong> (1 g, 4.77 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (1.41 g, 4.77 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound lb (475 mg, 3.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 4 / petroleum ether 6). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 120 mg of a white solid. Yield = 9.7% rHNM (DMSO,200 MHz) delta 4.45 (2H, d, J = 5.6 Hz), 6.99 (4H, m), 7.65 (1H, d), 7.73 (1H, d), 7.85 (1H, bs), 8.62 (1H, bs), 1 1.04 (1H, bs); [M+1] 386.6 (C16HnClF3N3O3 requires 385.73).
In ethyl acetate; at 0 - 80℃; for 4h; Example 28: 1-(4-chloro-2-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea scheme 1) Preparation of 1-(4-chloro-2-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available <strong>[771583-81-4]4-chloro-2-trifluoromethylbenzylamine</strong> (1 g, 4.77 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (1.41 g, 4.77 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1b (475 mg, 3.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 4 / petroleum ether 6). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 120 mg of a white solid. Yield = 9.7% 1HNMR (DMSO, 200 MHz) delta 4.45 (2H, d, J = 5.6 Hz), 6.99 (4H, m), 7.65 (1H, d), 7.73 (1H, d), 7.85 (1H, bs), 8.62 (1H, bs), 11.04 (1H, bs); [M+1] 386.6 (C16H11ClF3N3O3 requires 385.73).
  • 3
  • [ 771583-81-4 ]
  • [ 1338064-66-6 ]
  • 4
  • [ 771583-81-4 ]
  • [ 100960-55-2 ]
  • [ 1338064-98-4 ]
YieldReaction ConditionsOperation in experiment
22.5% With diethyl cyanophosphonate; In tetrahydrofuran; at 0 - 80℃; 2,3-dihydro-2-oxobenzo[d]oxazole-4-carboxylic acid 21 (260 mg, 1.45 mmol) was dissolved in 20 ml of THF and at 0C DEPC (0.260 ml, 1.2equiv) and 4-chloro-2-trifluorobenzylamine (0.25 ml, 1.2equiv.) were added to the solution. The mixture was warmed at 80C overnight, then evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column using AcOEt 3 / petroleum ether 7 as eluant gave l l Omg of a white solid. Yield = 22.5% 'HNMR (DMSO, 200 MHz) delta 4.58 (2H, d, J = 5.8 Hz), 7.16 (1H, t, J = 8 Hz), 7.42 (1H, dd, J = 8.2 Hz, J' = 1 Hz), 7.55 (2H, d, J = 8.2 Hz), 7.65 (3H, m), 9.29 (1H, bt), 1 1.60 (1H, bs); [M+1] 336.9 (C 16H1 1F3N2O3 requires 336.3).
  • 5
  • [ 771583-81-4 ]
  • [ 1624255-71-5 ]
  • [ 1624256-18-3 ]
  • 6
  • [ 771583-81-4 ]
  • [ 619-21-6 ]
  • N-(4-chloro-2-(trifluoromethyl)benzyl)-3-formylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% Dissolve 3-formylbenzoic acid (1.0g, 6.7mmol), HATU (3.8g, 10.0mmol) and DIPEA (2.6g, 20.0mmol) in tetrahydrofuran (20mL), stir at room temperature for 0.5 hours, and add 4- Chloro-2- (trifluoromethyl) benzylamine (1.4 g, 6.7 mmol) was reacted at room temperature for 4 hours, and an appropriate amount of water was added, followed by extraction with ethyl acetate three times. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to give the title compound (2.1 g, yield: 92%) in this step.
  • 7
  • [ 771583-81-4 ]
  • 3-((4-chloro-2-(trifluoromethyl)benzyl)carbamoyl)benzoic acid [ No CAS ]
  • 8
  • [ 771583-81-4 ]
  • N1-(4-chloro-2- (trifluoromethyl)benzyl)-N<SUP>3</SUP>-(4-(ethylsulfonyl)benzyl)isophthalamide [ No CAS ]
  • 9
  • [ 771583-81-4 ]
  • 5-((4-(ethylsulfonyl)benzyl)carbamoyl)-2-fluorobenzoic acid [ No CAS ]
  • N<SUP>3</SUP>-(4-chloro-2-(trifluoromethyl)benzyl)-N<SUP>1</SUP>-(4-(ethylsulfonyl)benzyl)-4-fluoroisophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% 5-((4- (ethylsulfonyl) benzyl) carbamoyl) -2-fluorobenzoic acid (150.0 mg, 0.4 mmol), HATU (234.0 mg, 0.6 mmol), and DIPEA (211.8 mg, 1.6 mmol) ) Dissolved in tetrahydrofuran (10mL), stirred at room temperature for 0.5 hours, then added 4-chloro-2- (trifluoromethyl) benzylamine (129.1mg, 0.6mmol), reacted at room temperature for 4 hours, then added an appropriate amount Water and extracted three times with ethyl acetate. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (100.0 mg, yield: 42%).
  • 10
  • [ 771583-81-4 ]
  • 5-((4-(ethylsulfonyl)benzyl)carbamoyl)-2- (2-fluoroethoxy)benzoic acid [ No CAS ]
  • N<SUP>3</SUP>-(4-chloro-2-(trifluoromethyl)benzyl)-N<SUP>1</SUP>-(4-(ethylsulfonyl)benzyl)-4-(2-fluoroethoxy)isophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% 5-((4- (ethylsulfonyl) benzyl) carbamoyl) -2- (2-fluoroethoxy) benzoic acid (200.0 mg, 0.5 mmol), HATU (278.6 mg, 0.7 mmol) and DIPEA (189.0 mg, 1.5 mmol) was dissolved in tetrahydrofuran (10 mL), and after stirring at room temperature for 0.5 hours, 4-chloro-2- (trifluoromethyl) benzylamine (153.6 mg, 0.7 mmol) was added. At room temperature After reacting for 4 hours, an appropriate amount of water was added and extraction was performed 3 times with ethyl acetate. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (150.0 mg, yield: 51%) in this step.
  • 11
  • [ 771583-81-4 ]
  • 5-((4-(ethylsulfonyl)benzyl)carbamoyl)-2-methoxybenzoic acid [ No CAS ]
  • N<SUP>3</SUP>-(4-chloro-2- (trifluoromethyl)benzyl)-N<SUP>1</SUP>-(4-(ethylsulfonyl)benzyl)-4-methoxyisophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% 5-((4- (ethylsulfonyl) benzyl) carbamoyl) -2-methoxybenzoic acid (150.0 mg, 0.4 mmol), HATU (302.2 mg, 0.8 mmol) and DIPEA (154.1 mg, 1.2 mmol) was dissolved in tetrahydrofuran (10 mL), and after stirring at room temperature for 0.5 hours, 4-chloro-2- (trifluoromethyl) benzylamine (125.0 mg, 0.6 mmol) was added, and the reaction was performed at room temperature for 4 hours. An appropriate amount of water was added and extracted three times with ethyl acetate. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (90.0 mg, yield: 38%).
  • 12
  • [ 771583-81-4 ]
  • 5-((4-(ethylsulfonyl)benzyl)carbamoyl)-2-isopropoxybenzoic acid [ No CAS ]
  • N<SUP>3</SUP>-(4-chloro-2-(trifluoromethyl)benzyl)-N<SUP>1</SUP>-(4-(ethylsulfonyl)benzyl)-4-isopropoxyisophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% 5-((4- (ethylsulfonyl) benzyl) carbamoyl) -2-isopropoxybenzoic acid (300.0 mg, 0.7 mmol), HATU (422.0 mg, 1.1 mmol) and DIPEA (477.2 mg , 3.7 mmol) was dissolved in tetrahydrofuran (10 mL), and after stirring at room temperature for 0.5 hours, 4-chloro-2- (trifluoromethyl) benzylamine (232.6 mg, 1.1 mmol) was added, and the reaction was performed at room temperature for 4 hours. Then, add an appropriate amount of water and extract 3 times with ethyl acetate. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (300.0 mg, yield: 65%).
  • 13
  • [ 771583-81-4 ]
  • 2-(difluoromethoxy)-5-((4-(ethylsulfonyl)benzyl)carbamoyl)benzoic acid [ No CAS ]
  • N<SUP>3</SUP>-(4-chloro-2-(trifluoromethyl)benzyl)-4-(difluoromethoxy)-N<SUP>1</SUP>-(4-(ethylsulfonyl)benzyl)isophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Add 2- (difluoromethoxy) -5-((4- (ethylsulfonyl) benzyl) carbamoyl) benzoic acid (100.0 mg, 0.2 mmol), HATU (184.0 mg, 0.5 mmol), and DIPEA (93.8 mg, 0.7 mmol) was dissolved in tetrahydrofuran (10 mL), and stirred at room temperature for 0.5 hours, then 4-chloro-2- (trifluoromethyl) benzylamine (60.8 mg, 0.3 mmol) was added and reacted at room temperature. After 4 hours, an appropriate amount of water was added, and extracted three times with ethyl acetate. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (24.0 mg, yield: 16%) in this step.
  • 14
  • [ 771583-81-4 ]
  • 4-((4-(ethylsulfonyl)benzyl)carbamoyl)benzoic acid [ No CAS ]
  • N1-(4-chloro-2-trifluoromethylbenzyl)-N4-(4-(ethylsulfonyl)benzyl)terephthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% 4-((4- (ethylsulfonyl) benzyl) carbamoyl) benzoic acid (100.0 mg, 0.29 mmol), HATU (164.2 mg, 0.43 mmol) and DIPEA (185.7 mg, 1.44 mmol) were dissolved in tetrahydrofuran ( 5 mL), after stirring at room temperature for 0.5 hours, <strong>[771583-81-4]4-chloro-2-trifluoromethylbenzylamine</strong> (60.6 mg, 0.29 mmol) was added, and the mixture was reacted at room temperature for 4 hours, and then an appropriate amount of water was added, followed by extraction with ethyl acetate. 3 times. The organic phases were combined and washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (80.0 mg, yield: 51%).
  • 15
  • [ 771583-81-4 ]
  • N1-(4-chloro-2-trifluoromethylbenzyl)-N4-(4-(ethylsulfonyl)benzyl)-N1-(2-fluoroethyl)terephthalamide [ No CAS ]
  • 16
  • [ 771583-81-4 ]
  • [ 762-49-2 ]
  • N-(4-chloro-2-trifluoromethylbenzyl)-2-fluoroethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With potassium carbonate; In acetonitrile; at 80℃; for 4h; <strong>[771583-81-4]4-chloro-2-trifluoromethylbenzylamine</strong> (100.0 mg, 0.5 mmol), 1-bromo-2-fluoroethane (78.7 mg, 0.6 mmol) and potassium carbonate (138.2 mg, 1.0 mmol) were dissolved in acetonitrile (5mL),The reaction was heated to 80 C for 4 hours. The reaction solution was cooled to room temperature. The reaction solution was concentrated. The concentrate was purified by preparative thin layer chromatography (eluent: petroleum ether: ethyl acetate = 4: 1 (v: v)) to obtain the title compound (40.0 mg, yield: 30%).
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