[ CAS No. 251115-21-6 ]

Name: 251115-21-6|4-Bromo-2-nitro-1-(trifluoromethyl)benzene|98%
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Quality Control of [ 251115-21-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 251115-21-6 ]

CAS No. :	251115-21-6	MDL No. :	MFCD11226284
Formula :	C₇H₃BrF₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WPDWGHAFCXNYDI-UHFFFAOYSA-N
M.W :	270.00 g/mol	Pubchem ID :	18371261
Synonyms :

Calculated chemistry of [ 251115-21-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.97
TPSA :	45.82 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) :	-5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.72
Log Po/w (XLOGP3) :	3.33
Log Po/w (WLOGP) :	4.53
Log Po/w (MLOGP) :	2.68
Log Po/w (SILICOS-IT) :	1.43
Consensus Log Po/w :	2.74

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.8
Solubility :	0.0431 mg/ml ; 0.00016 mol/l
Class :	Soluble
Log S (Ali) :	-3.97
Solubility :	0.029 mg/ml ; 0.000107 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.52
Solubility :	0.0821 mg/ml ; 0.000304 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 251115-21-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 251115-21-6 ]

* 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 [ 251115-21-6 ]
Downstream synthetic route of [ 251115-21-6 ]

[ 251115-21-6 ] Synthesis Path-Upstream 1~2

1
[ 251115-21-6 ]
[ 703-91-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iron; ammonium chloride In tetrahydrofuran; ethanol; water at 80℃; for 1 h;	To a suspension of 4-bromo-2-nitro- 1 -(trifluoromethyl)benzene (4.0 g, 14.9mmol) in ethanol (23OmL), THF (85mL), and water (4OmL) was added ammonium chloride (1.0 g, 18.8mmol) and ferrous powder (5.06 g, 90mmol). The resulting mixture was heated at 80 ⁰C for 1 hr and the progress of the reaction was monitored by TLC. Upon complete consumption of staring material, the reaction mixture was filtered off while it was hot. The filtrate was evaporated under vacuum and the crude residue was diluted with ethyl acetate (10OmL) and washed with water (3 x 5OmL). The combined organic layer was washed with brine, dried over Na₂SO₄ and evaporated under vacuum to afford 5-bromo-2-(trifluoromethyl)aniline as a solid (3.2g, 90percent).
79%	at 0 - 20℃; for 2 h;	5-bromo-2-(trifluoromethyl)aniline (1) : To a solution of 4-bromo-2-nitro-l- (trifluoromethyl)benzene (2.0 g, 7.4 mmol) in acetic acid (10.0 mL), Iron powder (1.2 g, 21.8 mmol) was added at 0 °C. The resulting reaction mixture was stirred at room temperature for 2 h. After completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was diluted with water, basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (2x50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 1 (1.4 g, 79percent) as a brown gummy solid. 1H NMR (400 MHz, DMSO-d₆): δ 5.86 (brs, 2H), 6.73-6.73 (dd, J = 1.2, 8.4 Hz, 1H), 7.02 (s, 1H), 7.23-7.25 (d, J = 8.4 Hz, 1H). MS m/z (M+H): 240.1

Reference： [1] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 100
[2] Patent: WO2014/149164, 2014, A1, . Location in patent: Paragraph 00763; 00895

2
[ 680-15-9 ]
[ 3460-18-2 ]
[ 251115-21-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(l) iodide In 1-methyl-pyrrolidin-2-one at 80℃;	To a solution of 1, 4-dibromo-2-nitrobenzene (5 g, 17.8mmol) in N- methylpyrrolidinone (4OmL) were added methyl difluoro(fluorosulfonyl)acetate (4.5mL, 35.6mmol) and copper(l) iodide. The mixture was heated at 80 ⁰C overnight, decolorized with activated charcoal, diluted with brine and extracted with ethyl acetate (3X3OmL). The combined extracts was dried over MgSO₄, concentrated in vacuum and purified by flash chromatography (0-lOOpercent ethyl acetate in petroleum) to give 4-bromo-2-nitro-l-(trifluoromethyl)benzene (4.1 g, 85percent) as a yellow oil.
85%	With copper(l) iodide In 1-methyl-pyrrolidin-2-one at 80℃;	b) 4-Bromo-2-nitro-1 -(trif luoromethyl)benzeneTo a solution of 1 ,4-dibromo-2-nitrobenzene (5 g, 17.8 mmol) in N- methylpyrrolidinone (40 mL) were added methyl difluoro(fluorosulfonyl)acetate (4.5 mL, 35.6 mmol) and copper(l) iodide. The mixture was heated at 80 ⁰C overnight, decolorized with activated charecoal, diluted with brine and extracted with ethyl acetate (3 x 30 mL). The combined extracts was dried over MgSOφ concentrated in EPO <DP n="69"/>vacuo and purified by flash chromatography (0-100percent ethyl acetate in hexanes) to give the title compound (4.1 g, 85percent) as a yellow oil. ¹ H NMR (400MHz, CDCI3) δ8.15 (s, 1 H), 7.90 (d, J = 8.1 Hz, 1 H), 7.75 (d, J = 8.1 Hz, 1 H).
85%	With copper(l) iodide In 1-methyl-pyrrolidin-2-one at 80℃; for 24 h;	PREPARATION 45 3-fluoro-3'-nitro-4'-(trifluoromethyl)-4-biphenylamine To a solution of 1,4-dibromo-2-nitrobenzene (5.0 g, 17.8 mMol) in 1-methyl-2-pyrrolidinone (25 mL) was added copper(I) iodide (0.85 g, 4.5 mMol) and methyl 2-(fluorosulfonyl)difluoroacetate (4.6 mL, 36.1 mMol). The reaction mixture was heated at 80° C. for 24 h. After cooling to room temperature, the reaction mixture was diluted with water and the organics were extracted with ethyl acetate, filtered to remove insolubles, washed with brine, dried over magnesium sulfate, and concentrated in vacuo. Purification of the residue by silica gel chromatography (5percent ethyl acetate/hexanes) gave the intermediate 4-bromo-2-nitro-1-(trifluoromethyl)benzene (4.10 g, 85percent) as a yellow oil. ¹H NMR (400 MHz, CDCl₃) δ 8.06 (d, 1H, J=1.5 Hz), 7.87-7.92 (m, 1H), 7.73 (d, 1H, J=8.3 Hz).

Reference： [1] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 100
[2] Patent: WO2006/113432, 2006, A2, . Location in patent: Page/Page column 67-68; 37
[3] Patent: US2007/142460, 2007, A1, . Location in patent: Page/Page column 18

[ 251115-21-6 ] Synthesis Path-Downstream 1~20

1
[ 251115-21-6 ]
[ 89415-43-0 ]
3'-nitro-4'-(trifluoromethyl)-4-biphenylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4939 - 4952

2
[ 680-15-9 ]
[ 3460-18-2 ]
[ 251115-21-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 80℃;	To a solution of 1, 4-dibromo-2-nitrobenzene (5 g, 17.8mmol) in N- methylpyrrolidinone (4OmL) were added methyl difluoro(fluorosulfonyl)acetate (4.5mL, 35.6mmol) and copper(l) iodide. The mixture was heated at 80 0C overnight, decolorized with activated charcoal, diluted with brine and extracted with ethyl acetate (3X3OmL). The combined extracts was dried over MgSO4, concentrated in vacuum and purified by flash chromatography (0-lOOpercent ethyl acetate in petroleum) to give 4-bromo-2-nitro-l-(trifluoromethyl)benzene (4.1 g, 85%) as a yellow oil.
85%	With copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 80℃;	b) 4-Bromo-2-nitro-1 -(trif luoromethyl)benzeneTo a solution of 1 ,4-dibromo-2-nitrobenzene (5 g, 17.8 mmol) in N- methylpyrrolidinone (40 mL) were added methyl difluoro(fluorosulfonyl)acetate (4.5 mL, 35.6 mmol) and copper(l) iodide. The mixture was heated at 80 0C overnight, decolorized with activated charecoal, diluted with brine and extracted with ethyl acetate (3 x 30 mL). The combined extracts was dried over MgSOphi concentrated in EPO <DP n="69"/>vacuo and purified by flash chromatography (0-100% ethyl acetate in hexanes) to give the title compound (4.1 g, 85%) as a yellow oil. 1 H NMR (400MHz, CDCI3) delta8.15 (s, 1 H), 7.90 (d, J = 8.1 Hz, 1 H), 7.75 (d, J = 8.1 Hz, 1 H).
85%	With copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 80℃; for 24h;	PREPARATION 45 3-fluoro-3'-nitro-4'-(trifluoromethyl)-4-biphenylamine To a solution of 1,4-dibromo-2-nitrobenzene (5.0 g, 17.8 mMol) in 1-methyl-2-pyrrolidinone (25 mL) was added copper(I) iodide (0.85 g, 4.5 mMol) and methyl 2-(fluorosulfonyl)difluoroacetate (4.6 mL, 36.1 mMol). The reaction mixture was heated at 80 C. for 24 h. After cooling to room temperature, the reaction mixture was diluted with water and the organics were extracted with ethyl acetate, filtered to remove insolubles, washed with brine, dried over magnesium sulfate, and concentrated in vacuo. Purification of the residue by silica gel chromatography (5% ethyl acetate/hexanes) gave the intermediate 4-bromo-2-nitro-1-(trifluoromethyl)benzene (4.10 g, 85%) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 8.06 (d, 1H, J=1.5 Hz), 7.87-7.92 (m, 1H), 7.73 (d, 1H, J=8.3 Hz).

Reference： [1]Patent: WO2010/91310,2010,A1 .Location in patent: Page/Page column 100
[2]Patent: WO2006/113432,2006,A2 .Location in patent: Page/Page column 67-68; 37
[3]Patent: US2007/142460,2007,A1 .Location in patent: Page/Page column 18

3
[ 251115-21-6 ]
[ 1051316-42-7 ]
6-[3-nitro-4-(trifluoromethyl)phenyl]-3,4-dihydro-2(1H)-quinolinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃;	c) 6-[3-Nitro-4-(trifluoromethyl)phenyl]-3,4-dihydro-2(1 H)-quinolinone To a solution of (2-oxo-1 ,2,3,4-tetrahydro-6-quinolinyl)boronic acid (720 mg,3.79 mmol) in dioxane (10 rtaunl_) and aqueous potassium carbonate (2 M, 10 mL) were added tetrakis(triphenylphosphine)palladium (0) (219 mg, 0.19 mmol) and 4-bromo- 2-nitro-1-(trifluoromethyl)benzene (1.0 g, 3.79 mmol). The mixture was heated at 90 0C overnight, cooled, poured into water and extracted with ethyl acetate (3 x 30 mL). The combined extracts were dried over MgSC>4, concentrated in vacuo and purified by flash chromatography (0-100% ethyl acetate in hexanes) to give the title compound (764 mg, 60%) as a yellow solid. 1 H NMR (400MHz, CDCI3) delta 8.27 (br s, 1 H), 8.07 (s, 1 H), 7.89 (d, J = 1.0 Hz 1 H), 7.49 (m, 2H), 6.93 (d, J = 8.8 Hz, 1 H), 3.31(t, J = 7.6 Hz, 2H), 2.74 (t, J = 7.6 Hz, 2H). MS(ES+) m/e 337 [M+H]+.

Reference： [1]Patent: WO2006/113432,2006,A2 .Location in patent: Page/Page column 68

4
[ 251115-21-6 ]
[ 703-91-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iron; ammonium chloride; In tetrahydrofuran; ethanol; water; at 80℃; for 1h;	To a suspension of 4-bromo-2-nitro- 1 -(trifluoromethyl)benzene (4.0 g, 14.9mmol) in ethanol (23OmL), THF (85mL), and water (4OmL) was added ammonium chloride (1.0 g, 18.8mmol) and ferrous powder (5.06 g, 90mmol). The resulting mixture was heated at 80 0C for 1 hr and the progress of the reaction was monitored by TLC. Upon complete consumption of staring material, the reaction mixture was filtered off while it was hot. The filtrate was evaporated under vacuum and the crude residue was diluted with ethyl acetate (10OmL) and washed with water (3 x 5OmL). The combined organic layer was washed with brine, dried over Na2SO4 and evaporated under vacuum to afford 5-bromo-2-(trifluoromethyl)aniline as a solid (3.2g, 90%).
79%	With iron; acetic acid; at 0 - 20℃; for 2h;	5-bromo-2-(trifluoromethyl)aniline (1) : To a solution of 4-bromo-2-nitro-l- (trifluoromethyl)benzene (2.0 g, 7.4 mmol) in acetic acid (10.0 mL), Iron powder (1.2 g, 21.8 mmol) was added at 0 C. The resulting reaction mixture was stirred at room temperature for 2 h. After completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was diluted with water, basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (2x50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 1 (1.4 g, 79%) as a brown gummy solid. 1H NMR (400 MHz, DMSO-d6): delta 5.86 (brs, 2H), 6.73-6.73 (dd, J = 1.2, 8.4 Hz, 1H), 7.02 (s, 1H), 7.23-7.25 (d, J = 8.4 Hz, 1H). MS m/z (M+H): 240.1

Reference： [1]Patent: WO2010/91310,2010,A1 .Location in patent: Page/Page column 100
[2]Patent: WO2014/149164,2014,A1 .Location in patent: Paragraph 00763; 00895

5
[ 7223-38-3 ]
[ 251115-21-6 ]
[ 1350816-39-5 ]