[ CAS No. 1548-62-5 ] {[proInfo.proName]}

Name: 1548-62-5|2-Nitro-6-(trifluoromethyl)phenol|98%
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SKU: A114914
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Quality Control of [ 1548-62-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1548-62-5 ]

SDS Specification

Alternatived Products of [ 1548-62-5 ]

Product Details of [ 1548-62-5 ]

CAS No. :	1548-62-5	MDL No. :	MFCD05155649
Formula :	C₇H₄F₃NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FMPKXGYPBUWNNG-UHFFFAOYSA-N
M.W :	207.11	Pubchem ID :	901834
Synonyms :

Calculated chemistry of [ 1548-62-5 ]

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 :	66.05 Å²

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) :	-5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.45
Log Po/w (XLOGP3) :	2.83
Log Po/w (WLOGP) :	3.47
Log Po/w (MLOGP) :	1.37
Log Po/w (SILICOS-IT) :	0.27
Consensus Log Po/w :	1.88

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.09
Solubility :	0.168 mg/ml ; 0.000809 mol/l
Class :	Soluble
Log S (Ali) :	-3.87
Solubility :	0.0276 mg/ml ; 0.000133 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.1
Solubility :	1.66 mg/ml ; 0.00802 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.79

Safety of [ 1548-62-5 ]

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

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.

Upstream synthesis route of [ 1548-62-5 ]
Downstream synthetic route of [ 1548-62-5 ]

[ 1548-62-5 ] Synthesis Path-Upstream 1~1

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

Yield	Reaction Conditions	Operation in experiment
47%	With sodium nitrate; sulfuric acid 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 (4percent MeOH/CH₂ Cl₂) gave the desired product(1.84 g, 47percent). ¹ H NMR (CD₃ COCD₃): δ 8.35 (d, 1H), 7.95 (d, 1H), 7.13 (t, 1H).
47%	With sodium nitrate; sulfuric acid 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 (4percentMeOH/CH₂ Cl₂) gave the desired product(1.84 g, 47percent). ¹ H NMR (CD3COCD3): d 8.35 (d,1H), 7.95 (d, 1H), 7.13 (t, 1H).
47%	With sodium nitrate; sulfuric acid 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 (4percentMeOH/CH₂CH₂) gave the desired product (1.84 g, 47percent). 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 0percent to 10percent EtOAc/hexane to yield the title compound (1.4 g, 44percent 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 0percent to 10percent EtOAc/hexane to yield the title compound (1.4 g, 44percent yield).

Reference： [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, # 22, p. 6842 - 6851

[ 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).

Reference： [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).

Reference： [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 ]

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

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

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

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

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

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

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

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

Reference： [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).

Reference： [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 ]