445-14-7|2-Amino-4-chlorobenzotrifluoride| Ambeed

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Quality Control of [ 445-14-7 ] Purity: 98% SDS Specification

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Product Details of [ 445-14-7 ]

CAS No. :	445-14-7
Formula :	C₇H₅ClF₃N
M.W :	195.57
SMILES Code :	C1=C(C(F)(F)F)C(=CC(=C1)Cl)N
MDL No. :	MFCD08282771
InChI Key :	GXMFVMMXHKXSBI-UHFFFAOYSA-N
Pubchem ID :	67963

Safety of [ 445-14-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 445-14-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	40.86
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.79
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.1
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.15
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.77
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.91

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.09
Solubility	0.159 mg/ml ; 0.000815 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.95
Solubility	0.219 mg/ml ; 0.00112 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.54
Solubility	0.0558 mg/ml ; 0.000285 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.54 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.33

Application In Synthesis of [ 445-14-7 ]

* 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 [ 445-14-7 ]

[ 445-14-7 ] Synthesis Path-Downstream 1~30

1
[ 438-39-1 ]
[ 445-14-7 ]

References: [1]Patent: DE672371,1935, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 25,p. 119.

2
[ 17178-10-8 ]
[ 445-14-7 ]
[ 79-04-9 ]
2-Chloro-N-(5-chloro-2-trifluoromethyl-phenyl)-N-(2-methoxy-ethyl)-acetamide [ No CAS ]

References: [1]Patent: AT341509,1977, .
Patent: DE2405479,1974, .
Chem.Abstr.,1974,vol. 81.

3
[ 75-63-8 ]
[ 108-42-9 ]
[ 445-14-7 ]
[ 445-13-6 ]
[ 432-21-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2293 - 2299.

5
[ 445-14-7 ]
[ 1106313-72-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of <strong>[445-14-7]2-(trifluoromethyl)-5-chloro-aniline</strong> (3.9 g, 19.5 mmol) in glacial acetic acid (120 ml) and conc. HCl (39 ml) is added sodium nitrite (1.39 g, 19.5 mmol) in water (16 ml). The reaction mixture is allowed to warm to room temperature and stirred for 3 hours, then added to a solution of SO2/AcOH/CuCl2/H2O (400 ml) (preparation of reagent described under Intermediate DI), and stirred at room temperature for 18 hours. The reaction mixture is poured onto ice/water (1.5 L), and extracted with EtOAc (3×300 ml). The combined organic layers are washed with 1N HCl and water, and dried (Na2SO4). Concentration in vacuo yields 5-Chloro-2-trifluoromethyl-benzenesulfonyl chloride.
663 mg		a) 5-chloro-2-(trifluoromethyl)benzene-1-sulfonyl Chloride Thionyl chloride (2 mL) was added dropwise to ice-cooled water (12 mL), and the mixture was stirred at 0 C. for 3 hr. To this solution was added copper(I) chloride (28 mg) to give solution A. To the ice-cooled concentrated hydrochloric acid (3 mL) was added <strong>[445-14-7]5-chloro-2-(trifluoromethyl)aniline</strong> (500 mg), and the mixture was stirred at 0 C. for 10 min. To the obtained mixture was added dropwise a solution of sodium nitrite (210 mg) in water (0.8 mL) at 0 C., and the mixture was stirred at 0 C. for 10 min. The obtained mixture was added dropwise to solution A at 0 C., and the mixture was stirred at 0 C. for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over magnesium sulfate and concentrated to give the title compound (663 mg). 1H NMR (300 MHz, DMSO-d6) delta 7.56-7.64 (1H, m), 7.68-7.76 (1H, m), 8.04 (1H, d, J=2.4 Hz).

References: [1]Patent: US2009/239847,2009,A1 .Location in patent: Page/Page column 44.
[2]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 0909; 0910.

6
[ 445-14-7 ]
[ 1301158-71-3 ]

References: [1]Journal of Fluorine Chemistry,2011,vol. 132,p. 263 - 268.

7
[ 445-14-7 ]
[ 1301158-73-5 ]

References: [1]Journal of Fluorine Chemistry,2011,vol. 132,p. 263 - 268.

8
[ 445-14-7 ]
[ 76-05-1 ]
[ 1301158-62-2 ]

References: [1]Journal of Fluorine Chemistry,2011,vol. 132,p. 263 - 268.

9
[ 1254781-51-5 ]
[ 445-14-7 ]
[ 1268356-15-5 ]

References: [1]Chinese Journal of Chemistry,2012,vol. 30,p. 2522 - 2532.

10
[ 445-14-7 ]
[ 1099597-32-6 ]

Yield	Reaction Conditions	Operation in experiment
100%		Example 5 3-((5-chloro-2-(trifluoromethyl)phenyl)ethvnyl)-5-(l-(piperidin-4-yl)-lH-pyrazol-4- yl)-lH-pyrrolor2,3-b1pyridine Step 1) 2-bromo-4-chloro-l-(trifluoromethyl)benzene To a stirred solution of 40percent HBr (2.20 mL, 15.34 mmol) in 0 (2 mL) was added 2-amino-4- chlorobenzotrifluoride (0.50 g, 2.56 mmol) at 0 °C. Then a solution of sodium nitrite (0.21 g, 3.07 mmol) in H20 (2 mL) was added dropwise at 0 °C. The mixture was stirred at 0 °C for a further 0.5 hours, a solution of cuprous bromide (0.63 g, 4.35 mmol) in 40percent HBr (2.20 mL, 15.34 mmol) and H20 (3 mL) was added. The mixture was stirred at 75 °C for 3 hours, then cooled to rt, and extracted with EtOAc (40 mL x 4). The combined organic phases were washed with brine (80 mL x 2), dried over anhydrous Na2S04 and concentrated in vacuo to give the title compound as a yellow liquid (0.76 g, 100percent). GC -MS: 257.9.
100%		40percent HBr (2.20 mL, 15.34 mmol) was dissolved in H2O (2 mL), then at 0 ° C,2-Amino-4-chlorobenzotrifluoride (0.50 g, 2.56 mmol) was added to the reaction mixture, followed by 0 ° C,An aqueous solution of sodium nitrite (sodium nitrite (0.21 g, 3.07 mmol) dissolved in 2 mL of water) was added dropwise to the reaction mixture.After the reaction solution was stirred at 0 ° C for half an hour, additional cuprous bromide (0.63 g, 4.35 mmol) of 40percent HBr (2.20 mL, 15.34 mmol) andA mixed solution of H2O (3 mL).The reaction solution was stirred at 75 ° C for 3 hours, and then cooled to room temperature.It was then extracted with ethyl acetate (40 mL x 4).The combined organic phases were washed with brine (80 mL x 2).Dry with anhydrous Na2SO4,The title compound was obtained as a yellow liquid after concentration under reduced pressure.(0.76g, 100percent).

References: [1]Patent: WO2014/89280,2014,A1 .Location in patent: Page/Page column 57.
[2]Patent: CN103833753,2017,B .Location in patent: Paragraph 0420; 0422; 0423.

11
[ 61350-00-3 ]
[ 445-14-7 ]

References: [1]ChemCatChem,2018,vol. 10,p. 965 - 970.

12
N-(5-chloro-2-(trifluoromethyl)phenyl)picolinamide [ No CAS ]
[ 445-14-7 ]

References: [1]ChemCatChem,2018,vol. 10,p. 965 - 970.

13
[ 445-14-7 ]
C₉H₅ClF₃NO₃ [ No CAS ]