[ CAS No. 125163-12-4 ] {[proInfo.proName]}

Name: 125163-12-4|4-Fluoro-5-methoxy-2-nitroaniline|98%
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SKU: A457449
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3d Animation Molecule Structure of 125163-12-4

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Quality Control of [ 125163-12-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 125163-12-4 ]

SDS Specification

Alternatived Products of [ 125163-12-4 ]

Product Details of [ 125163-12-4 ]

CAS No. :	125163-12-4	MDL No. :	MFCD00247494
Formula :	C₇H₇FN₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FRMLKSWJWIKLPO-UHFFFAOYSA-N
M.W :	186.14	Pubchem ID :	53216869
Synonyms :

Calculated chemistry of [ 125163-12-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.12
TPSA :	81.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.33
Log Po/w (XLOGP3) :	1.69
Log Po/w (WLOGP) :	1.75
Log Po/w (MLOGP) :	0.49
Log Po/w (SILICOS-IT) :	-0.59
Consensus Log Po/w :	0.93

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.27
Solubility :	1.0 mg/ml ; 0.00539 mol/l
Class :	Soluble
Log S (Ali) :	-3.01
Solubility :	0.183 mg/ml ; 0.000983 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.83
Solubility :	2.77 mg/ml ; 0.0149 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.98

Safety of [ 125163-12-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 125163-12-4 ]

* 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 [ 125163-12-4 ]

[ 125163-12-4 ] Synthesis Path-Downstream 1~6

1
[ 67-56-1 ]
[ 78056-39-0 ]
[ 125163-12-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydroxide; at 20℃; for 20h;	To a suspension of commercially available <strong>[78056-39-0]4,5-difluoro-2-nitroaniline</strong> 24 (10 g, 57.44 mmol) in methanol (200 mL) was added KOH,2 M (60 mL, 120 mmol) and the mixture was stirred vigorously at room temperature for 20 h. The mixture was concentrated under reduced pressure, the residue was taken up in dichloromethane (500 mL) and washed with water (100 mL), dried over sodium sulfateand concentrated under reduced pressure to give the product as a yellow solid, 10.77 g (quant). MS (ESP) m/z 187 (MH+); 1H NMR(DMSO-d6) delta: 7.75 (d, 1H); 7.52 (br s, 2H); 6.63 (d, 1H); 3.87 (s, 3H).
		EXAMPLE 72; Preparation of 4-fluoro-5-methoxy-2-nitroaniline; [0148] To an ice cooled 100 ml round bottom flask charged with 30 ml of methanol was added 0.40 g (17.4 mmol) of sodium. After the solution was homogeneous, Ig (5.71 mmol) of 4,5 difluoro, 2-nitro aniline was added. The solution turns a bright yellow and a precipitate slowly forms. After 1 hour the solution was concentrated and 2N HCl added to the residue. The mixture was extracted with ethyl acetate (3 X 30 ml) and the organic layers combined, dried (MgStheta4) and concentrated to yield a yellow solid.IH NMR (CDCl3): delta 7.83 (d,lH, ArH), 6.20 (d,lH,ArH), 6.18 (bs, 2H, NH2), 3.92(s,3H,CH3);MS (ESI) m/z 185 ([M-H]-);Anal, calcd for C7H7FN2O3: C:45.17 H:3.79 N:15.05 Found: C:45.77 H:3.92 N:14.05.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5392 - 5409
[2]Synthesis,2013,vol. 45,p. 272 - 280
[3]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 1517 - 1523
[4]Patent: WO2006/68928,2006,A1 .Location in patent: Page/Page column 64

2
[ 458-11-7 ]
[ 125163-12-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 1517 - 1523

3
[ 124-41-4 ]
[ 104222-34-6 ]
[ 125163-12-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	In methanol; at 100℃; for 3.0h;Sealed tube;	A mixture of <strong>[104222-34-6]5-chloro-4-fluoro-2-nitroaniline</strong> (200 mg,1.05 mmol) and sodium methoxide (567 mg, 10.5 mmol) in methanol (10 mL) was heated at 100 C in a sealed tube for 3 h. Then the solution was cooled to room temperature, diluted with 20 mL ofwater, extracted with EtOAc (3 50 mL) and washed with brine.The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give intermediate 2 as a yellow solid (176 mg,yield 90%). Rf 0.5 (CH2Cl2/MeOH: 50/1); 1H NMR (400 MHz, CDCl3)d 7.85 (d, J 11.6 Hz, 1H), 6.21 (d, J 7.2 Hz, 3H), 3.91 (s, 3H).

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 80,p. 535 - 542

4
[ 78056-39-0 ]
[ 125163-12-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium methylate In methanol	1 Step 1: Step 1: Preparation of 4-fluoro-5-methoxy-2-nitroaniline To an ice cooled 100 ml round bottom flask charged with methanol (30 mL) was added sodium methoxide (1.551 g, 28.7 mmol). After the solution was homogeneous, 4,5-difluoro-2-nitroaniline (2 g, 11.49 mmol) was added portion wise. The solution turns a bright yellow and slowly yellow precipitation was observed. Solvent was removed under reduced pressure and the residue was diluted with water and acidified using 1.5N HCl solution. The aqueous layer was extracted with ethyl acetate twice, the combined organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated to dryness to get 4-fluoro-5-methoxy-2-nitroaniline (1.8 g, 9.48 mmol, 82% yield) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.76 (d, J=12.55 Hz, 1H) 7.54 (br. s., 2H) 6.65 (s, 1H) 3.86 (s, 3H). 19F NMR: δ ppm -147.64 (1F); MS:MS m/z 185.2 (M+-1)

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; BIOCON LIMITED - US2015/376233, 2015, A1

5
[ 78056-39-0 ]
[ 124-41-4 ]
[ 125163-12-4 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 20℃; for 12h;	35.1 Step 1: preparation of 4-fluoro-5-methoxy-2-nitroaniline Step 1: preparation of 4-fluoro-5-methoxy-2-nitroaniline 3.4g 2-amino-4,5-difluoronitrobenzene was added to a 100mL round-bottomed flask, and dissolved by adding 30mL MeOH. 2.16g sodium methoxide was slowly added at room temperature. The mixture was reacted for another 12h at room temperature before the reaction was stopped. The reaction solution was filtered, and the filter cake was washed with 10mL cold MeOH, and dried in vacuum to give the title compound, which was used directly in the next step. LC-MS m/z: [M+H]+ =187.

Reference： [1]Current Patent Assignee: NANJING SANHOME INVESTMENT GROUP CO LTD - EP2940031, 2015, A1 Location in patent: Paragraph 0147

6
[ 58743-83-2 ]
[ 125163-12-4 ]
N-(4-fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy[1,1'-biphenyl]-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium tertiary butoxide; dicyclohexyl[2’,4’,6’-tris(propan-2-yl)[1,1’-biphenyl]-2-yl]phosphane In toluene at 100℃; for 16h;	9.1 Step 1: N-(4-Fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy-[1,1'-biphenyl]-4-amine. A mixture of 4-fluoro-5-methoxy-2-nitroaniline (155 mg, 0.84 mmol), 1-bromo-4-(4-methoxyphenyl)benzene (200 mg, 0.76 mmol), tris(dibenzylideneacetone)dipalladium(0) (35 mg, 0.04 mmol), XPhos (36 mg, 0.08 mmol), sodium tert-butoxide (146 mg, 1.52 mmol), and toluene (2 mL) was degassed with 2 vacuum/N2 cycles, stirred at 100 °C for 16 h, and then allowed to cool to rt. The mixture was diluted with EtOAc (15 mL) and water (10 mL). Celite was added, and the mixture was filtered through Celite. The filter cake was washed with EtOAc (10 mL). The organic layer was washed with brine (10 mL), dried (Na2SO4), filtered, concentrated, and then purified by silica gel chromatography (0-15% EtOAc in hexanes) to give N-(4-fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy-[1,1'-biphenyl]-4-amine (73 mg, 26%) as an orange solid. 1H NMR (400 MHz, DMSO-d6): δ 9.74 (s, 1H), 8.02 (d, J = 11.9 Hz, 1H), 7.67 (m, 4H), 7.48 (d, J = 8.6 Hz, 2H), 7.04 (d, J = 8.8 Hz, 2H), 6.85 (d, J = 7.8 Hz, 1H), 3.83-3.81 (m, 3H), 3.81-3.80 (m, 3H); LCMS: 369.2 [M+H]+.
26%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium tertiary butoxide; dicyclohexyl[2’,4’,6’-tris(propan-2-yl)[1,1’-biphenyl]-2-yl]phosphane In toluene at 100℃; for 16h;	9.1 Step 1: N-(4-Fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy-[1,1'-biphenyl]-4-amine. A mixture of 4-fluoro-5-methoxy-2-nitroaniline (155 mg, 0.84 mmol), 1-bromo-4-(4-methoxyphenyl)benzene (200 mg, 0.76 mmol), tris(dibenzylideneacetone)dipalladium(0) (35 mg, 0.04 mmol), XPhos (36 mg, 0.08 mmol), sodium tert-butoxide (146 mg, 1.52 mmol), and toluene (2 mL) was degassed with 2 vacuum/N2 cycles, stirred at 100 °C for 16 h, and then allowed to cool to rt. The mixture was diluted with EtOAc (15 mL) and water (10 mL). Celite was added, and the mixture was filtered through Celite. The filter cake was washed with EtOAc (10 mL). The organic layer was washed with brine (10 mL), dried (Na2SO4), filtered, concentrated, and then purified by silica gel chromatography (0-15% EtOAc in hexanes) to give N-(4-fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy-[1,1'-biphenyl]-4-amine (73 mg, 26%) as an orange solid. 1H NMR (400 MHz, DMSO-d6): δ 9.74 (s, 1H), 8.02 (d, J = 11.9 Hz, 1H), 7.67 (m, 4H), 7.48 (d, J = 8.6 Hz, 2H), 7.04 (d, J = 8.8 Hz, 2H), 6.85 (d, J = 7.8 Hz, 1H), 3.83-3.81 (m, 3H), 3.81-3.80 (m, 3H); LCMS: 369.2 [M+H]+.

Reference： [1]Current Patent Assignee: METACRINE INC - WO2022/72491, 2022, A1 Location in patent: Paragraph 00417
[2]Current Patent Assignee: METACRINE INC - WO2022/72491, 2022, A1 Location in patent: Paragraph 00417

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H221	Flammable gas
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H305	May be harmful if swallowed and enters airways
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H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
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H316	Causes mild skin irritation
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H320	Causes eye irritation
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H401	Toxic to aquatic life
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H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 125163-12-4 ] {[proInfo.proName]}

Quality Control of [ 125163-12-4 ]

Related Doc. of [ 125163-12-4 ]

Product Details of [ 125163-12-4 ]

Calculated chemistry of [ 125163-12-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 125163-12-4 ]

Application In Synthesis of [ 125163-12-4 ]

[ 125163-12-4 ] Synthesis Path-Downstream 1~6

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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