[ CAS No. 394-25-2 ] {[proInfo.proName]}

Name: 394-25-2|4-Methoxy-3-nitrobenzotrifluoride|98%
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SKU: A193305
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Quality Control of [ 394-25-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 394-25-2 ]

SDS Specification

Alternatived Products of [ 394-25-2 ]

Product Details of [ 394-25-2 ]

CAS No. :	394-25-2	MDL No. :	MFCD00007099
Formula :	C₈H₆F₃NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MAAFHLOZHBKYTG-UHFFFAOYSA-N
M.W :	221.13	Pubchem ID :	96748
Synonyms :

Calculated chemistry of [ 394-25-2 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.76
TPSA :	55.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.68
Log Po/w (XLOGP3) :	2.26
Log Po/w (WLOGP) :	3.77
Log Po/w (MLOGP) :	1.68
Log Po/w (SILICOS-IT) :	0.75
Consensus Log Po/w :	2.03

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.73
Solubility :	0.409 mg/ml ; 0.00185 mol/l
Class :	Soluble
Log S (Ali) :	-3.05
Solubility :	0.196 mg/ml ; 0.000886 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.8
Solubility :	0.35 mg/ml ; 0.00158 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.92

Safety of [ 394-25-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501	UN#:	1759
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 394-25-2 ]

* 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 [ 394-25-2 ]
Downstream synthetic route of [ 394-25-2 ]

[ 394-25-2 ] Synthesis Path-Upstream 1~4

1
[ 121-17-5 ]
[ 367-86-2 ]
[ 32137-19-2 ]
[ 394-25-2 ]
[ 40700-38-7 ]
[ 400-99-7 ]

Reference： [1] Journal of Organic Chemistry, 1991, vol. 56, # 22, p. 6406 - 6411

2
[ 121-17-5 ]
[ 367-86-2 ]
[ 32137-19-2 ]
[ 394-25-2 ]
[ 40700-38-7 ]
[ 400-99-7 ]

Reference： [1] Journal of Organic Chemistry, 1991, vol. 56, # 22, p. 6406 - 6411

3
[ 394-25-2 ]
[ 349-65-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen In methanol at 20℃;	Example 51Synthesis of 4-(8-methoxy-5- (trifluorornethyl) quinazolin-2-ylamino) phenyl)(moφholino)methanone (Compound 500) <n="365"/>PP028218.0002Step 1. Preparation of 2-methoxy-5- (trifluoromethyl) anilineA mixture of 4-methoxy-3-nitrobezotrifluoride and 10percent of 10percent Pd / C in methanol was stirred under Hfe atmosphere overnight at room temperature. The reaction mixture was filtered through celite, concentrated and dried under vacuum to provide product as an off white solid in 99percentyield. ES/MS m/z 192.1 (MH⁺).

Reference： [1] Synthesis, 2006, # 19, p. 3316 - 3340
[2] Patent: WO2007/117607, 2007, A2, . Location in patent: Page/Page column 363-364
[3] Journal of the American Chemical Society, 1952, vol. 74, p. 3011,3012
[4] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1955, vol. 28, p. 969,972[5] Chem.Abstr., 1956, p. 4880
[6] Journal of the Chemical Society, 1954, p. 3852
[7] Journal of the Chemical Society, 1949, p. Spl. 113
[8] Patent: EP617023, 1994, A1,
[9] Patent: US5475015, 1995, A,

4
[ 394-25-2 ]
[ 7439-89-6 ]
[ 349-65-5 ]

Reference： [1] Patent: US4388472, 1983, A,

[ 394-25-2 ] Synthesis Path-Downstream 1~31

1
[ 367-86-2 ]
[ 394-25-2 ]

Reference： [1]Journal of the Chemical Society,1949,p. Spl. 113

2
[ 394-25-2 ]
[ 349-65-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃;	Example 51Synthesis of 4-(8-methoxy-5- (trifluorornethyl) quinazolin-2-ylamino) phenyl)(mophiholino)methanone (Compound 500) <n="365"/>PP028218.0002Step 1. Preparation of 2-methoxy-5- (trifluoromethyl) anilineA mixture of 4-methoxy-3-nitrobezotrifluoride and 10% of 10% Pd / C in methanol was stirred under Hfe atmosphere overnight at room temperature. The reaction mixture was filtered through celite, concentrated and dried under vacuum to provide product as an off white solid in 99%yield. ES/MS m/z 192.1 (MH+).
	palladium; In ethanol;	EXAMPLE 1 2-Methoxy-5-trifluoromethyl-aniline. 2-Methoxy-5-trifluoromethyl-nitrobenzene (283 mmol, 62,67 g) suspended in ethanol (500 ml) is hydrogenated over palladium on carbon 5% (1.7 g) and the reaction mixture is filtered through celite. The filtrate is concentrated in vacuo yielding the title compound as light grey crystals M.p. 61C.
	palladium; In ethanol;	EXAMPLE 1 2-Methoxy-5-trifluoromethyl-aniline. 2-Methoxy-5-trifluoromethyl-nitrobenzene (283 mmol, 62,67 g) suspended in ethanol (500 ml) is hydrogenated over palladium on carbon 5% (1.7 g) and the reaction mixture is filtered through celite. The filtrate is concentrated in vacuo yielding the title compound as light grey crystals M.p. 61 C.

Reference： [1]Synthesis,2006,p. 3316 - 3340
[2]Patent: WO2007/117607,2007,A2 .Location in patent: Page/Page column 363-364
[3]Journal of the American Chemical Society,1952,vol. 74,p. 3011,3012
[4]Zhurnal Prikladnoi Khimii,1955,vol. 28,p. 969,972
Chem.Abstr.,1956,p. 4880
[5]Journal of the Chemical Society,1954,p. 3852
[6]Journal of the Chemical Society,1949,p. Spl. 113
[7]Patent: EP617023,1994,A1
[8]Patent: US5475015,1995,A

3
[ 394-25-2 ]
[ 7626-26-8 ]
[ 2377-31-3 ]

Reference： [1]Journal of the Chemical Society,1954,p. 3852
[2]Journal of the Chemical Society,1954,p. 3852

4
[ 121-17-5 ]
[ 394-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; In methanol;	(a) Preparation of 4-methoxy-3-nitro-benzotrifluoride 4-chloro-3-nitrobenzotrifluoride (112.8 g) in methanol (200 ml) was mixed with a solution of sodium (11.6 g) in methanol (800 ml) and stirred for 2 hours. The mixture was kept overnight and then stirred and heated under reflux for 3 hours. The solution was left overnight, filtered, and the solvent removed. The remaining oil was taken up in ether (500 ml) and washed with water. The ether solution was dried and evaporated to give 4-methoxy-3-nitrobenzotrifluoride (106 g).

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 3011,3012
[2]Patent: US4388472,1983,A
[3]Patent: US2056899,1935,

5
[ 121-17-5 ]
[ 367-86-2 ]
[ 32137-19-2 ]
[ 394-25-2 ]
[ 40700-38-7 ]
[ 400-99-7 ]
C₁₄H₆F₇NO₃ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6406 - 6411

6
[ 71-23-8 ]
[ 394-25-2 ]
[ 837-99-0 ]

Reference： [1]Journal of general chemistry of the USSR,1963,vol. 33,p. 131 - 133
Zhurnal Obshchei Khimii,1963,vol. 33,p. 138 - 141

7
[ 64-17-5 ]
[ 394-25-2 ]
[ 655-08-3 ]

Reference： [1]Journal of general chemistry of the USSR,1963,vol. 33,p. 131 - 133
Zhurnal Obshchei Khimii,1963,vol. 33,p. 138 - 141

8
[ 123-51-3 ]
[ 394-25-2 ]
[ 1492-74-6 ]

Reference： [1]Journal of general chemistry of the USSR,1963,vol. 33,p. 131 - 133
Zhurnal Obshchei Khimii,1963,vol. 33,p. 138 - 141

9
[ 78-83-1 ]
[ 394-25-2 ]
[ 787-33-7 ]

Reference： [1]Journal of general chemistry of the USSR,1963,vol. 33,p. 131 - 133
Zhurnal Obshchei Khimii,1963,vol. 33,p. 138 - 141

10
[ 71-41-0 ]
[ 394-25-2 ]
[ 1692-96-2 ]

Reference： [1]Journal of general chemistry of the USSR,1963,vol. 33,p. 131 - 133
Zhurnal Obshchei Khimii,1963,vol. 33,p. 138 - 141

11
[ 394-25-2 ]
[ 71-36-3 ]
[ 787-34-8 ]

Reference： [1]Journal of general chemistry of the USSR,1963,vol. 33,p. 131 - 133
Zhurnal Obshchei Khimii,1963,vol. 33,p. 138 - 141

15
[ 394-25-2 ]
[ 324-14-1 ]

Reference： [1]Zhurnal Prikladnoi Khimii,1955,vol. 28,p. 969,972
Chem.Abstr.,1956,p. 4880

16
[ 394-25-2 ]
[ 398-10-7 ]

Reference： [1]Zhurnal Prikladnoi Khimii,1955,vol. 28,p. 969,972
Chem.Abstr.,1956,p. 4880

17
[ 394-25-2 ]
[ 316-75-6 ]

Reference： [1]Journal of the Chemical Society,1954,p. 3852

18
[ 352-32-9 ]
[ 394-25-2 ]

Reference： [1]Journal of the Chemical Society,1949,p. Spl. 113

19
[ 402-44-8 ]
[ 394-25-2 ]

Reference： [1]Journal of the Chemical Society,1949,p. Spl. 113

20
[ 394-25-2 ]
[ 40622-64-8 ]

Reference： [1]Journal of the Chemical Society,1949,p. Spl. 113

21
[ 402-42-6 ]
[ 394-25-2 ]

Reference： [1]Journal of the Chemical Society,1949,p. Spl. 113

22
[ 79-24-3 ]
[ 121-17-5 ]
[ 394-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dimethyl sulfoxide; toluene;	STR6 Sodium methoxide (1.35 g; 25 mmol; 2.5 equiv) was slurried in DMSO (10 mL) and cooled in a cool water bath. Nitroethane (0.79 mL; 11 Immol; 1.1 equiv) and 4-chloro-3-nitrobenzotrifluoride (1; 1.49 mL; 10 mmol) were mixed and added slowly dropwise with cooling such that the temperature remained between 15 and 20 C. After the addition was complete, the reaction mixture was allowed to warm slowly over 3 h from 15 to 18 C. and then stirred overnight at 18 C. to completely consume 1 according to GC analysis. Toluene (10 mL) was added and the mixture was cooled in ice water and 3 N HCl (10 mL; 30 mmol; 3 equiv) was added dropwise such that the temperature remained below 20 C. After the addition the layers were separated, and the organic solution was dried (Na2 SO4) and concentrated to afford 2.60 g of crude product. Analysis of this material by 1 H NMR and GC indicated that the major product was 6 with 2 and 3 as minor products.
	With sodium methylate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dimethyl sulfoxide; toluene;	Comparative Example 1 : 4-Methoxy-3-nitrobenzotrifluoride (6): Sodium methoxide (1.35 g; 25 mmol; 2.5 equiv) was slurried in DMSO (10 mL) and cooled in a cool water bath. Nitroethane (0.79 mL; 11 mmol; 1.1 equiv) and 4-chloro-3-nitrobenzotrifluoride (1; 1.49 mL; 10 mmol) were mixed and added slowly dropwise with cooling such that the temperature remained between 15 and 20C. After the addition was complete, the reaction mixture was allowed to warm slowly over 3 h from 15 to 18C and then stirred overnight at 18C to completely consume 1 according to GC analysis. Toluene (10 mL) was added and the mixture was cooled in ice water and 3 N HCl (10 mL; 30 mmol; 3 equiv) was added dropwise such that the temperature remained below 20C. After the addition the layers were separated, and the organic solution was dried (Na2SO4) and concentrated to afford 2.60 g of crude product. Analysis of this material by 'H NMR and GC indicated that the major product was 6 with 2 and 3 as minor products. 6: 1H NMR (CDCl3) delta 8.127 (d, 1H, J = 1.8 Hz); 7.803 (dd, 1 H, J = 2.1, 8.7 Hz); 7.203 (d, 1H, J = 9.06 Hz); 4.028 (s, 3H). GC (30 m DB-17, 100C, 3 min; 100-280C, 15/min; 280C, 1 min): tR 9.35 min

Reference： [1]Patent: US6096929,2000,A
[2]Patent: EP988276,2003,B1

23
[ 394-25-2 ]
[ 2181-42-2 ]
[ 1239985-92-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; at 10 - 20℃; for 5.0h;	l-methoxy-3-methyl-2-nitro-4- (trifluoromethyl)benzene was prepared by a procedure similar to that described in "Synthesis of 3, 6-Disubstituted 2-Nitrotoluenes by Methylation of Aromatic Nitro Compounds withDimethylsulfonium Methylide", Kitano, Masafumi, Ohashi Naohito, Synthetic Communications, 30(23), 4247-4254, 2000. To a suspension of NaH (60% by wt. in mineral oil, 362 mg, 9.04 mmol) and trimethylsulfonium iodide (1.84 g, 9.04 mmol) in DMSO (17 ml) and THF (6.7 ml) was added 4-methoxy-3- nitrobenzotrifluoride (1.00 g, 4.52 mmol) as a solution in DMSO (2.7 ml) . The reaction mixture was allowed to stir at 10-200C for 5 hrs . The reaction mixture was quenched by addition to ice water. The aqueous layer was separated and extracted with toluene 7 times. The combined organic extracts were washed with brine, dried over MgSO4, and filtered. The solvent was removed by distillation at reduced pressure. The residue was purified by automated silica gel chromatography (100% hexanes to 98:2 hexanes :ethylacetate) to provide l-methoxy-3-methyl-2-nitro-4- (trifluoromethyl)benzene.

Reference： [1]Patent: WO2006/44823,2006,A2 .Location in patent: Page/Page column 137

24
[ 394-25-2 ]
[ 7439-89-6 ]
[ 349-65-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; isopropyl alcohol; toluene;	(b) Preparation of 3-amino-4-methoxy benzotrifluoride 4-Methoxy-3-nitrobenzotrifluoride (95 g) in isopropanol (1.0 liter) and water (250 ml) was mixed with concentrated hydrochloric acid (15 ml). Iron powder (180 g) was added and the mixture was heated and stirred under reflux. After 90 minutes the mixture was cooled to 50 C. and filtered. The residue was washed with isopropanol and the combined filtrates evaporated. The residue was dissolved in toluene and the solution dried (MgSO4) and evaporated. The residue was triturated with light petroleum (b.p. 30-40) to give the 3-amino-4-methoxybenzotrifluoride as a colourless solid (68 g).

Reference： [1]Patent: US4388472,1983,A

25
[ 394-25-2 ]
[ 159117-83-6 ]