[ CAS No. 69411-05-8 ] {[proInfo.proName]}

Name: 69411-05-8|3-Chloro-5-trifluoromethylaniline|98%
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SKU: A135464
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Quality Control of [ 69411-05-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 69411-05-8 ]

CAS No. :	69411-05-8	MDL No. :	MFCD02684210
Formula :	C₇H₅ClF₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OVENUGPMQDFGLE-UHFFFAOYSA-N
M.W :	195.57	Pubchem ID :	3017933
Synonyms :

Calculated chemistry of [ 69411-05-8 ]

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 :	26.02 Å²

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) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.71
Log Po/w (XLOGP3) :	2.75
Log Po/w (WLOGP) :	4.1
Log Po/w (MLOGP) :	3.15
Log Po/w (SILICOS-IT) :	2.77
Consensus Log Po/w :	2.9

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.09
Solubility :	0.159 mg/ml ; 0.000815 mol/l
Class :	Soluble
Log S (Ali) :	-2.95
Solubility :	0.219 mg/ml ; 0.00112 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.54
Solubility :	0.0558 mg/ml ; 0.000285 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.37

Safety of [ 69411-05-8 ]

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

Application In Synthesis of [ 69411-05-8 ]

* 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.

Upstream synthesis route of [ 69411-05-8 ]
Downstream synthetic route of [ 69411-05-8 ]

[ 69411-05-8 ] Synthesis Path-Upstream 1~1

1
[ 401-93-4 ]
[ 69411-05-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With tin(ll) chloride In ethyl acetate for 3 h; Heating / reflux	To a stirred mixture of l-chloro-3-nitro-5-(trifluoromethyl)benzene (2.90 g, 12.9 mmoL) in 120 mL of EtOAc, was added SnCl₂ dihydrate (12.0 g, 51.6 mmoL). This mixture was heated to reflux for 3 h and cooled to room temperature. Next, the mixture was diluted with 100 mL of EtOAc and washed with 2.5N NaOH solution (Ix 150 mL). The aqueous layer was separated and extracted with EtOAc (Ix 200 mL). Combined EtOAc layers were washed with brine (Ix 40 mL), dried (MgSO₄), filtered and concentrated in vacuo to give 2.51 g of Preparation 65A (3- chloro-5-(trifluoromethyl)aniline) as a yellow solid in quantitative yield.[00495] HPLC: 2.57 min (RT) (Chromolith SpeedROD column 4.6 x 50 mm, 10- 90percent aqueous MeOH over 4 minutes containing 0.2percent phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z=196 [M+H]⁺.

Reference： [1] Patent: WO2009/3077, 2008, A1, . Location in patent: Page/Page column 135
[2] Patent: US2003/158409, 2003, A1,
[3] Patent: US2002/10181, 2002, A1,
[4] Patent: US5599814, 1997, A,

[ 69411-05-8 ] Synthesis Path-Downstream 1~59

1
[ 24451-15-8 ]
[ 69411-05-8 ]
N-(4-Bromo-phenyl)-N'-(3-chloro-5-trifluoromethyl-phenyl)-oxalamide [ No CAS ]

Reference： [1]Patent: FR1516276,1968,
Chem.Abstr.,1969,vol. 70

2
[ 24451-18-1 ]
[ 69411-05-8 ]
N-(3-Chloro-5-trifluoromethyl-phenyl)-N'-(2,4-dimethyl-phenyl)-oxalamide [ No CAS ]

Reference： [1]Patent: FR1516276,1968,
Chem.Abstr.,1969,vol. 70

3
[ 18522-98-0 ]
[ 69411-05-8 ]
N-(3-Chloro-5-trifluoromethyl-phenyl)-N'-p-tolyl-oxalamide [ No CAS ]

Reference： [1]Patent: FR1516276,1968,
Chem.Abstr.,1969,vol. 70

4
[ 69411-05-8 ]
[ 5397-14-8 ]
N-(4-Chloro-phenyl)-N'-(3-chloro-5-trifluoromethyl-phenyl)-oxalamide [ No CAS ]

Reference： [1]Patent: FR1516276,1968,
Chem.Abstr.,1969,vol. 70

5
[ 69411-05-8 ]
[ 18522-99-1 ]
[ 22505-30-2 ]

Reference： [1]Patent: FR1516276,1968,
Chem.Abstr.,1969,vol. 70

6
[ 69411-05-8 ]
3-Chloro-5-trifluoromethyl-benzenediazonium; chloride [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 1243 - 1257

7
[ 69411-05-8 ]
[ 96406-91-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 1243 - 1257

8
[ 69411-05-8 ]
[ 24095-92-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 1243 - 1257

9
[ 69411-05-8 ]
[ 101094-85-3 ]
[ 300842-56-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;SiO2; In 1,4-dioxane; methanol; ethanol; hexane; water; ethyl acetate;	Example 13 1-(5-Chloro-3-trifluormethyl-anilino)-4-(4-pyridyl-methyl)-phthalazine A suspension of 27.9 g (109 mMol) of 1-chloro-4-(4-pyridyl-methyl)-phthalazine (Example 67A.1 in WO 98/35958) and 21.4 g (109 mMol) of 5-amino-3-chloro-benzotrifluoride (Example 5b) in 500 ml of ethanol and 27.4 ml of 4 N HCl/dioxane is stirred during 3 h a 80 C. After cooling down, the reaction mixture is diluted with 0.3 l of ether, filtrated, and washed with ether. The remaining solid is then taken up in water and EtOAc, brought to alkaline pH by means of NH3 solution, stirred for 15 min at room temperature and then filtered and washed with ether (?raw product). The water layer is removed from the filtrate and extracted twice with ethyl acetate. The organic layers are washed with water and brine, dried over Na2SO4 and evaporated. The residue is combined with the raw product mentioned above, and the solid is dissolved in ethyl acetate and methanol. About 100 g SiO2 are added, followed by evaporation, and the powder is applied onto a silica gel column and eluted with ethyl acetate and subsequently with a mixture of ethyl acetate and methanol (98:2?95:5, v/v). Solving the obtained fractions in ethyl acetate/methanol, partial evaporation and crystallization by addition of ether/hexane leads to the title compound: m.p. 231-232 C.; An. calc. (C21H14N4ClF3) C, 60.81%; H, 3.40%; N, 13.51%; Cl, 8.55%; F, 13.74%; An meas. C, 60.8%; H, 3.4%; N, 13.5%; Cl, 8.5%; F, 13.8%; 1H-NMR (DMSO-d6) 9.63 (s, HN), 8.60 (d, 1H), 8.56 (s, 1H), 8.44 (d, 2H), 8.39 (s, 1H), 8.16 (d, 1H), 8.03 (t, 1H), 7.97 (t, 1H), 7.43 (s, 1H), 7.32 (d, 2H), 4.63 (s, 2H); FAB-MS (M+H)+=415.

Reference： [1]Patent: US2003/13718,2003,A1

10
[ 401-93-4 ]
[ 69411-05-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With tin(ll) chloride; In ethyl acetate; for 3h;Heating / reflux;	To a stirred mixture of l-chloro-3-nitro-5-(trifluoromethyl)benzene (2.90 g, 12.9 mmoL) in 120 mL of EtOAc, was added SnCl2 dihydrate (12.0 g, 51.6 mmoL). This mixture was heated to reflux for 3 h and cooled to room temperature. Next, the mixture was diluted with 100 mL of EtOAc and washed with 2.5N NaOH solution (Ix 150 mL). The aqueous layer was separated and extracted with EtOAc (Ix 200 mL). Combined EtOAc layers were washed with brine (Ix 40 mL), dried (MgSO4), filtered and concentrated in vacuo to give 2.51 g of Preparation 65A (3- chloro-5-(trifluoromethyl)aniline) as a yellow solid in quantitative yield.[00495] HPLC: 2.57 min (RT) (Chromolith SpeedROD column 4.6 x 50 mm, 10- 90% aqueous MeOH over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z=196 [M+H]+.
	In methanol; aluminum nickel;	Step 2 92 g (0.408 mol) of <strong>[401-93-4]5-chloro-3-trifluoromethyl-nitrobenzene</strong> in 1 l of methanol are hydrogenated in the presence of 10.17 g of Raney nickel. The reaction mixture is filtered through Celite/activated carbon and the residue washed with methanol. Concentration of the filtrate by evaporation yields the oily 5-amino-3-chloro-benzotrifluoride; 1H-NMR (DMSO-d6) delta6.80 (m, 3H), 5.92 (s, H2N).
	In methanol; aluminum nickel;	111b 5-Amino-3-chloro-benzotrifluoride In the presence of 10.17 g of Raney nickel, 92 g (0.408 mol) of <strong>[401-93-4]5-chloro-3-trifluoromethyl-nitrobenzene</strong> are hydrogenated in 1 liter of methanol. The reaction mixture is filtered over Celite/activated carbon and the residue is washed with methanol. Concentration of the filtrate by evaporation yields the oily title compound: 1H-NMR (DMSO-d6) 6.80 (m, 3H), 5.92 (s, H2N); FAB-MS (M+H)+=196.

b. 3-Chloro-5-trifluoromethylaniline Using a procedure similar to that described in Example 20a except starting with [401-93-4]3-chloro-5-trifluoromethylnitrobenzene, the title compound was obtained (77%) as an amber oil; MS(CI): 196 (M+H). 250-MHz 1 H NMR (DMSO-d6): 6.82 (s, 1H), 6.79 (s, 1H), 6.77 (s, 1H), 5.94 (s, 2H).

Reference： [1]Patent: WO2009/3077,2008,A1 .Location in patent: Page/Page column 135
[2]Patent: US2003/158409,2003,A1
[3]Patent: US2002/10181,2002,A1
[4]Patent: US5599814,1997,A

11
[ 69411-05-8 ]
[ 327-78-6 ]
[ 941604-45-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	In tetrahydrofuran; at 20℃;	To a solution of <strong>[69411-05-8]3-Chloro-5-trifluoromethyl-aniline</strong> (425 mul, 3.1 mmol, 1.03 eq.) in dry THF (15 ml) was added 4-Chloro-3-(trifluoromethyl)-phenylisocyanate (665 mg, 3.0 mmol). After stirring overnight at rt the mixture was diluted with cHexane (100 ml), washed twice with 2 N HCl, once with sat. NaHCO3 and brine (100 ml each) and adsorbed on Celite in vacuo. Flash chromatography on silica with cHexane/TBME (4:1 to 2:1) yielded 952 mg product (76%) as a white powder. 1H NMR (DMSO) delta 9.43 (s, 2H), 8.10 (d, J=2.5 Hz, 1H), 7.84 (m, 2H), 7.69 (dd, J=9.0, 2.5 Hz, 1H), 7.64 (d, J=9.0 Hz, 1H), 7.45 (s). MS (ES-): 414.9.

Reference： [1]Patent: US2009/23813,2009,A1 .Location in patent: Page/Page column 3

12
[ 108-24-7 ]
[ 69411-05-8 ]
[ 349-63-3 ]

Yield	Reaction Conditions	Operation in experiment
94%		To a stirred mixture of Preparation 65A (2.51 g, 12.9 mmoL) in EtOH (130 mL) was added acetic anhydride (15.0 mL, 159 mmoL). The mixture was stirred at room temperature for 17 h. The mixture was then poured into a mixture of <n="137"/>40 mL of ice, 10 mL of saturated NaHCCh solution and 60 mL of EtOAc. The aqueous layer was separated and extracted with EtOAc (1 x 60 mL). The combined EtOAc layers were washed with brine (Ix 20 mL), dried (MgSO4), filtered and concentrated in vacuo to give 2.88 g of Preparation 65B in 94% yield. [00497] HPLC: 2.84 min (RT)(Chromolith SpeedROD column 4.6 x 50 mm, 10- 90% aqueous MeOH over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z=238 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta ppm 10.4 (s, IH, NH) 7.96 (s, IH) 7.91 (s,l H) 7.50 (s, IH), 2.09 (s, 3H).

Reference： [1]Patent: WO2009/3077,2008,A1 .Location in patent: Page/Page column 135-136

13
[ 69411-05-8 ]
[ 1885-14-9 ]
[ 884340-21-0 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2255 - 2264

14
[ 69411-05-8 ]
[ 875167-01-4 ]

Yield	Reaction Conditions	Operation in experiment
84%		A solution of NaN02 (6.50g) was added to a suspension of 3-chloro-5- (trifluoromethyl)aniline (18.44g) in concentrated HCI / acetic acid (83ml_ / 30ml_) at 0C and the mixture stirred for one hour. The diazonium salt formed was transferred into a saturated solution of sulfur dioxide in glacial acetic acid (350ml_) at 0C and the mixture was warmed up to room temperature for one hour. The mixture was poured onto ice-water and extracted with diethyl ether. The combined organic layers were washed with sodium hydrogen carbonate, dried over sodium sulphate, concentrated and purified by silica chromatography eluting with ethyl actetate / hexane to yield 3- chloro-5-(trifluoromethyl)benzenesulfonyl chloride (22g, 84%).1H NMR (400 MHz, Chloroform-D) d ppm 8.0 (m, 1 H) 8.2 (m, 1 H) 8.2 (t, J=1.9 Hz, 1 H)
84%		Intermediate 1 3-Chloro-5-(trifluoromethyl)benzenesulfonyl chloride [0115] [0116] A solution of NaNO2 (6.50 g) was added to a suspension of <strong>[69411-05-8]3-chloro-5-(trifluoromethyl)aniline</strong> (18.44 g) in concentrated HCl/acetic acid (83 mL/30 mL) at 0 C. and the mixture stirred for one hour. The diazonium salt formed was transferred into a saturated solution of sulfur dioxide in glacial acetic acid (350 mL) at 0 C. and the mixture was warmed up to room temperature for one hour. The mixture was poured onto ice-water and extracted with diethyl ether. The combined organic layers were washed with sodium hydrogen carbonate, dried over sodium sulphate, concentrated and purified by silica chromatography eluting with ethyl actetate/hexane to yield 3-chloro-5-(trifluoromethyl)benzenesulfonyl chloride (22 g, 84%). [0117] 1H NMR (400 MHz, Chloroform-D) d ppm 8.0 (m, 1H) 8.2 (m, 1H) 8.2 (t, J=1.9 Hz, 1H).

Reference： [1]Patent: WO2011/141729,2011,A1 .Location in patent: Page/Page column 16
[2]Patent: US2013/116270,2013,A1 .Location in patent: Paragraph 0115; 0116; 0117

15
[ 69411-05-8 ]
[ 51512-09-5 ]
[ 1450730-36-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5195 - 5198

16
[ 610-94-6 ]
[ 69411-05-8 ]
N-(3-chloro-5-(trifluoromethyl)phenyl)anthranilic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9110 - 9121

17
[ 610-94-6 ]
[ 69411-05-8 ]
N-(3-chloro-5-(trifluoromethyl)phenyl)anthranilic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9110 - 9121

18
trans-1'-tert-butyl-4'-ethyl-3-iodo-2-oxo-[1,3'-bipiperidine]-1',4'-dicarboxylate [ No CAS ]
[ 69411-05-8 ]
trans-1'-tert-butyl 4'-ethyl 3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-2-oxo-[1,3'-b]piperidinej-1',4’-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		[0092] Synthesis of trans-V-tert-buty 4'-ethyl 3-((3-chloro-5-(trifluoromethyl) phenyl)amino)-2-oxo-[l,3'-bipiperidine]- ,4'-dicarboxylate. A 1.0 M solution of lithium bis(trimethyldisilyl)amide in THF (13 mL, 12 mmol, 2.0 equiv) was added through an addition funnel at 10-15 C to a solution of <strong>[69411-05-8]3-chloro-5-(trifluoromethyl)aniline</strong> (15 g, 78 mmol, 1.2 equiv) in THF (13 mL). The mixture was allowed to stir at room temperature for 20 min and a solution of crude trans- -tert-butyl-4'-ethyl-3-iodo-2-oxo-[l,3'-bipiperidine]- ,4'- dicarboxylate 9 (3.7 g, 65 mmol, 1.0 equiv) in THF (13 mL) was added through an addition funnel at 10-15 C over 30 min. After addition, the reaction was allowed to stir at the temperature for 30 min. Upon completion, the reaction was cooled to 5 C and quenched slowly with water (10 mL), keeping the temperature below 20 C. The quenched reaction was extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with saturated brine (30 mL), dried (Na2S04), filtered, and concentrated in vacuo. The resulting crude product was purified over silica gel eluting with a gradient of 10% to 75%> of EtOAc in heptanes to give the desire product 10. ESI- MS (M+H-56) +: 463.1. 1H NMR (400 MHz, CDC13) delta: 6.92 (s, 1H), 6.71-6.69 (m, 2H), 4.17- 4.06 (m, 4H), 3.78-3.68 (m, 2H), 3.46-3.36 (m, 3H), 3.23-3.07 (m, 2H), 2.73-2.65 (m, 1H), 2.44- 2.37 (m, 1H), 2.03-1.85 (m, 3H), 1.71-1.61 (m, 2H), 1.46 (s, 9H), 1.27-1.19 (m, 3H).

Reference： [1]Patent: WO2013/185084,2013,A1 .Location in patent: Paragraph 0092

19
[ 1510832-77-5 ]
[ 69411-05-8 ]
[ 1510832-80-0 ]

Reference： [1]Patent: WO2013/185082,2013,A2 .Location in patent: Page/Page column 0146

20
[ 69411-05-8 ]
N-[4'-(3-amino-[1,2,4]oxadiazol-5-ylamino)-6'-chloro-2'-trifluoromethyl-biphenyl-3-yl]-methanesulfonamide [ No CAS ]
N-[4'-(5-amino-[1,2,4]oxadiazol-3-ylamino)-6'-chloro-2'-trifluoromethyl-biphenyl-3-yl]-methanesulfonamide [ No CAS ]