1548-62-5|2-Nitro-6-(trifluoromethyl)phenol| Ambeed

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Quality Control of [ 1548-62-5 ] Purity: 98% SDS Specification

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Product Details of [ 1548-62-5 ]

CAS No. :	1548-62-5
Formula :	C₇H₄F₃NO₃
M.W :	207.11
SMILES Code :	OC1=C(C(F)(F)F)C=CC=C1[N+]([O-])=O
MDL No. :	MFCD05155649
InChI Key :	FMPKXGYPBUWNNG-UHFFFAOYSA-N
Pubchem ID :	901834

Safety of [ 1548-62-5 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H317-H318-H410
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Computational Chemistry of [ 1548-62-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	6.0
Num. H-bond donors	1.0
Molar Refractivity	42.29
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.45
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	2.83
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.47
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.	1.37
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	0.27
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.88

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.09
Solubility	0.168 mg/ml ; 0.000809 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.	-3.87
Solubility	0.0276 mg/ml ; 0.000133 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	-2.1
Solubility	1.66 mg/ml ; 0.00802 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	No
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.	-5.55 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	0.0
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	2.0 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)	1.79

Application In Synthesis of [ 1548-62-5 ]

* 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 [ 1548-62-5 ]

[ 1548-62-5 ] Synthesis Path-Downstream 1~17

1
[ 444-30-4 ]
[ 1548-62-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium nitrate; sulfuric acid;sodium nitrite; In dichloromethane;	a) Preparation of 2-nitro-6-trifluoromethylphenol 2-trifluoromethylphenol (3.00 g, 18.5 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.73 g, 20.4 mmol). The addition of sulfuric acid (23 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2 Cl2) gave the desired product(1.84 g, 47%). 1 H NMR (CD3 COCD3): delta 8.35 (d, 1H), 7.95 (d, 1H), 7.13 (t, 1H).
47%	With sodium nitrate; sulfuric acid;sodium nitrite; In dichloromethane;	a)Preparation of 2-nitro-6-trifluoromethylphenol 2-trifluoromethylphenol (3.00 g, 18.5 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.73 g, 20.4 mmol). The addition of sulfuric acid (23 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2 Cl2) gave the desired product(1.84 g, 47%). 1 H NMR (CD3COCD3): d 8.35 (d,1H), 7.95 (d, 1H), 7.13 (t, 1H).
47%	With sodium nitrate; sulfuric acid;sodium nitrite; In dichloromethane;	a) Preparation of 2-nitro-6-trifluoromethylphenol 2-trifluoromethylphenol (3.00 g, 18.5 mmol) was dissolved in methylene chloride (40 mL) followed by the addition of sodium nitrate (1.73 g, 20.4 mmol). The addition of sulfuric acid (23 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2CH2) gave the desired product (1.84 g, 47%). 1H NMR(CD3COCD3): d 8.35 (d, 1H), 7.95 (d, 1H), 7.13 (t, 1H).

44%	With Concentrated HNO3; In AcOH;	17A. 2-Nitro-6-(trifluoromethyl)phenol To a solution of commercially available 2-trifluoromethylphenol (2.5 g, 15.42 mmol) in AcOH (3 mL) cooled to 0 C. was added dropwise concentrated HNO3 (1.5 mL). After the addition, the mixture was stirred at at 0 C. for 5 min, at rt for 10 min, then poured into ice/water, and extracted with ether (3*). The combined ether extracts were washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluding with 0% to 10% EtOAc/hexane to yield the title compound (1.4 g, 44% yield).
44%	With Concentrated HNO3; In acetic acid;	17A. 2-Nitro-6-(trifluoromethyl)phenol To a solution of commercially available 2-trifluoromethylphenol (2.5 g, 15.42 mmol) in AcOH (3 mL) cooled to 0 C. was added dropwise concentrated HNO3 (1.5 mL). After the addition, the mixture was stirred at at 0 C. for 5 min, at rt for 10 min, then poured into ice/water, and extracted with ether (3*). The combined ether extracts were washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluding with 0% to 10% EtOAc/hexane to yield the title compound (1.4 g, 44% yield).

References: [1]Patent: US5886044,1999,A .
[2]Patent: US5780483,1998,A .
[3]Patent: US6262113,2001,B1 .
[4]Patent: US2004/19063,2004,A1 .
[5]Patent: US2004/181064,2004,A1 .
[6]Journal of Organic Chemistry,1962,vol. 27,p. 4660 - 4662.
[7]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6842 - 6851.

3
[ 1548-62-5 ]
[ 7772-99-8 ]
[ 72534-45-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethanol;	a) Preparation of 3-trifluoromethyl-2-hydroxyaniline To the solution of <strong>[1548-62-5]2-trifluoromethyl-6-nitrophenol</strong> (4.2 g, 20.3 mmol) in ethanol (20 ml, Tin (II) chloride (22.9 g, 101 mmol) was added. The reaction mixture was stirred at reflux for about 4 hours, tThen it was cooled to room temperature. The NaHCO3 (aq) was added until pH=7 was obtained and then the mixture was extracted with ethyl acetate (3*). The combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give desired product (3.4 g, 94%). EI-MS m/z 178 (M+).
88%	In ethanol;	b) Preparation of 2-amino-6-trifluoromethylphenol A mixture of 6-trifluoromethyl-2-nitrophenol(1.84 g, 8.67 mmol) and tin (II) chloride (6.0 g, 26.2 mmol) in ethanol(150 mL) was heated at 80 C. under argon. After 2 hours, the starting material has disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2 Cl2) gave the desired product(1.35 g, 88%). 1 H NMR (CD3 OD): delta 6.93 (d, 1H), 6.82 (t, 1H), 6.78 (d, 1H).
88%	In ethanol;	b)Preparation of 2-amino-6-trifluoromethylphenol A mixture of 6-trifluoromethyl-2-nitrophenol(1.84 g, 8.67 mmol) and tin (II) chloride (6.0 g, 26.2 mmol) in ethanol(150 mL) was heated at 80 C. under argon. After 2 hours, the starting material has disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2 Cl2) gave the desired product(1.35 g, 88%). 1 H NMR (CD3 OD): d 6.93 (d, 1H), 6.82 (t, 1H), 6.78 (d, 1H).

References: [1]Patent: US6271261,2001,B1 .
[2]Patent: US5886044,1999,A .
[3]Patent: US5780483,1998,A .

4
[ 358-23-6 ]
[ 1548-62-5 ]
C₈H₃F₆NO₅S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6842 - 6851.

5
[ 1548-62-5 ]
C₂₃H₂₀F₇NO₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6842 - 6851.

6
[ 1548-62-5 ]
C₂₃H₂₂F₇NO₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6842 - 6851.

7
[ 1548-62-5 ]
C₂₄H₂₁F₁₀NO₄S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6842 - 6851.

8
[ 1548-62-5 ]
[ 609852-10-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6842 - 6851.

9
[ 1548-62-5 ]
[ 72534-45-3 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium 10% on activated carbon; hydrogen; In methanol; water; at 20.0℃; under 1551.49 Torr; for 3.0h;	Step A: 2-amino-6-(trifluoromethyl) phenol A 30 ml hydrogen bottle was charged with <strong>[1548-62-5]2-nitro-6-(trifluoromethyl)phenol</strong> (1.3 g, 6.3 mmol) in MeOH, and wet Pd/C(130 mg , purity: 10%) was added under 2 protection. The reaction mixture was degassed and charged by H2 (30 psi), then the reaction mixture was stirred at room temperature for 3 h. TLC (petroleum ether: EtOAc= 2: 1) showed that the starting material was consumed. The solvent was evaporated to give the desired product, which was directly used in the next step. 1HNMR (CDC13, 400 MHz): delta 6.91 (d, J=8.4 Hz, 2 H), 6.83 (t, J=8.0 Hz, 1 H).

References: [1]Patent: WO2016/49099,2016,A1 .Location in patent: Page/Page column 151.

10
[ 1548-62-5 ]
2-(4-bromophenyl)-8-(trifluoromethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]