[ CAS No. 113512-71-3 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 113512-71-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 113512-71-3 ]

SDS Specification

Alternatived Products of [ 113512-71-3 ]

Product Details of [ 113512-71-3 ]

CAS No. :	113512-71-3	MDL No. :	MFCD04973718
Formula :	C₆H₅F₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CXADAFQCFSVRGN-UHFFFAOYSA-N
M.W :	145.11	Pubchem ID :	2782999
Synonyms :

Calculated chemistry of [ 113512-71-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	32.79
TPSA :	46.25 ?2

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) :	-6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.22
Log Po/w (XLOGP3) :	1.09
Log Po/w (WLOGP) :	2.1
Log Po/w (MLOGP) :	1.68
Log Po/w (SILICOS-IT) :	1.5
Consensus Log Po/w :	1.52

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.87
Solubility :	1.96 mg/ml ; 0.0135 mol/l
Class :	Very soluble
Log S (Ali) :	-1.65
Solubility :	3.22 mg/ml ; 0.0222 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.0
Solubility :	1.45 mg/ml ; 0.01 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.26

Safety of [ 113512-71-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 113512-71-3 ]

* 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 [ 113512-71-3 ]

[ 113512-71-3 ] Synthesis Path-Downstream 1~12

1
[ 3282-30-2 ]
[ 113512-71-3 ]
[ 152169-44-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride; sodium chloride; In pyridine;	(4) 18.9 g (130 mmol) of the above <strong>[113512-71-3]5-amino-2,4-difluorophenol</strong> was dissolved in 45 mL of pyridine, 16.0 mL of pivaloyl chloride was added dropwise under ice-cooling and the mixture was stirred at the same temperature for 30 minutes. 1N hydrochloric acid was added to the reaction solution and the mixture was extracted with ether. The organic layer was washed once with 1N hydrochloric acid, once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was triturated with n-hexane to give 27.0 g of 2,4-difluoro-5-pivaloylaminophenol (yield: 91%). NMR (90MHz, CDCl3) delta (ppm) 1.35 (s, 9H), 6.90 (t, 1H, J=10.4Hz), 7.65 (brs, 1H), 7.94 (brs, 1H), 8.24 (dd, 1H, J=9.1, 8.0Hz) MS (M/Z) 229 (M+) Molecular formula C11H13F2NO2=229
	With hydrogenchloride; In pyridine;	5-Amino-2,4-difluorophenol (18.9 g, 130 mmol) obtained above was dissolved in pyridine (45mL) and pivaloyl chloride (16.0 mL) was added dropwise to the mixture for 8 minutes under ice-cooling. The reaction mixture was stirred for additional 30 minutes at the same temperature. Hydrochloric acid (1 N) was added to the reaction mixture and the mixture was extracted with ether. The organic layer was washed with 1 N hydrochloric acid, water, and brine once respectively, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was triturated to give 2,4-difluoro-5-pivaloylaminophenol (27.0 g, yield: 91%). 1H NMR (90 MHz, CDCl3) delta (ppm) 1.35 (s, 9H), 6.90 (t, J = 10.4Hz, 1H), 7.65 (brs, 1H), 7.94 (brs, 1H), 8.24 (dd, J = 9.1, 8.0Hz, 1H) EI-MS (m/e) 229 M+molecular formula C11H13F2NO2= 229

Reference： [1]Synthesis,1997,p. 1446 - 1450
[2]Patent: EP638566,1995,A1
[3]Patent: EP755928,1997,A1

2
[ 113512-57-5 ]
[ 113512-71-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	carbon palladium; In nitrogen; ethyl acetate;	(3) 24.9 g (142 mmol) of the above 2,4-difluoro-5-nitrophenol was dissolved in 150 mL of ethyl acetate, 5.0 g of 10% palladium/carbon was added and the mixture was stirred at 50 to 60 C for 27 hours under a stream of hydrogen. The gaseous phase in the reaction vessel was substituted with nitrogen, the reaction solution was filtered by suction and the solvent was distilled off under reduced pressure. The residue was triturated with n-hexane to give 19.8 g of 5-amino-2,4-difluorophenol (yield: 96%). NMR (90MHz, CDCl3) delta (ppm) 4.75 (brs, 2H), 6.37 (t, 1H, J=9.1Hz), 6.87 (t, 1H, J=11.1Hz), 9.21 (s, 1H) MS (M/Z) 145 (M+) Molecular formula C6H5F2NO=145
96%	With hydrogen;palladium dihydroxide; In ethyl acetate; for 6h;	To a suspension of 2,4-difluoro-5-nitrophenol (1.01 g, 5.77 mmol) in EtOAc was added palladium hydroxide (0.08 g, 0.57 mmol) and the resulting slurry was stirred under a hydrogen atmosphere for 6 h. The mixture was filtered through a Celite pad, washing with EtOAc (2*10 mL) and the filtrate was concentrated to afford 5-amino-2,4-difluorophenol (0.8 g, 96% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) delta 9.28 (s, 1H), 6.91 (t, J=7.2 Hz, 1H), 6.35 (t, J=8.8 Hz, 1H), 4.84 (brs, 2H); MS (ESI) m/z: 146.0 (M+H+).
96%	With hydrogen; palladium(II) hydroxide; In ethyl acetate; for 6h;	To a suspension of 2,4-difluoro-5-nitrophenol (1.01 g, 5.77 mmol) in EtOAc was added palladium hydroxide (0.08 g, 0.57 mmol) and the resulting slurry was stirred under a hydrogen atmosphere for 6h. The mixture was filtered through a Celite pad, washing with EtOAc (2x10 mL) and the filtrate was concentrated to afford 5-amino-2,4- difluorophenol (0.8 g, 96% yield) as a solid. FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO-i/6) delta 9.28 (s, 1H), 6.91 (t, J = 7.2 Hz, 1H), 6.35 (t, J = 8.8 Hz, 1H), 4.84 (brs, 2H); MS (ESI) m/z: 146.0 (M+H+).

94.6%	With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20℃; for 16h;	To a stirred solution of 2,4- difluoro-5-nitrophenol (1, 25 g, 0.143 mol) in EtOAc (200 mL), 10% Pd/C (4.55 g, 0.043 mol) was added. The reaction mixture was stirred at RT under H2 for 16 h. After the reaction completion (TLC), the reaction mixture was filtered by using celite bed, washed with EtOAc (1000 mL) and concentrated under reduced pressure to afford 5-amino-2,4- difluorophenol (2) as off brown solid (20.10 g, 94.6%); LCMS (ESI positive ion) m/z: calculated: 145.03; observed: 146.2 (M+l).
	palladium on activated carbon; In nitrogen; ethyl acetate;	2,4-Difluoro-5-nitrophenol (24.9 g, 142 mmol) obtained above was dissolved in ethyl acetate (150 mL) and 10% palladium on activated carbon (5.0 g) was added to the mixture. The reaction mixture was stirred under hydrogen stream at 50 to 60 C for 27 hours. After the atmosphere in reactor was replaced with nitrogen, the reaction mixture was filtrated with suction. The solvent in filtrate was distilled off under reduced pressure, the residue was triturated with hexane to give 5-amino-2,4-difluorophenol (19.8 g, yield: 96%). 1H NMR (90 MHz, CDCl3) delta (ppm) 4.75 (brs, 2H), 6.37 (t, J = 9.1 Hz, 1H), 6.87 (t, J = 11.1 Hz, 1H), 9.21 (s, 1H) EI-MS (m/e) 145 M+molecular formula C6H5F2NO = 145

Reference： [1]Synthesis,1997,p. 1446 - 1450
[2]Patent: EP638566,1995,A1
[3]Patent: US2008/90856,2008,A1 .Location in patent: Page/Page column 35
[4]Patent: WO2013/36232,2013,A2 .Location in patent: Paragraph 00225
[5]Patent: WO2018/178338,2018,A1 .Location in patent: Page/Page column 142
[6]Patent: EP755928,1997,A1

3
[ 2457-47-8 ]
[ 113512-71-3 ]
5-(5-chloropyridin-3-yloxy)-2,4-difluorobenzenamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%		To a solution of <strong>[113512-71-3]5-amino-2,4-difluorophenol</strong> (0.3 g, 2.07 mmol) in DMSO (2 mL) was added potassium t-butoxide (0.23 g, 2.07 mmol) at RT. After stirring for 1 h, 3,5-dichloropyridine (0.37 g, 2.5 mmol) and potassium carbonate (0.14 g, 1 mmol) were added and the mixture was heated to 190 C. for 1 h in microwave reactor. Water (30 mL) was added, and the product was extracted with EtOAc (2*35 mL) and the combined organic layers were washed with brine solution, dried (Na2SO4), concentrated in vacuo and purified by chromatography (EtOAc/hexane) to afford 5-(5-chloropyridin-3-yloxy)-2,4-difluorobenzenamine (0.35 g, 66% yield) as a solid. 1H NMR (400 MHz, Acetone-d6) delta 8.33-8.30 (m, 2H), 7.44 (t, J=2.4 Hz, 1H), 7.13 (t, J=10.8 Hz, 1H), 6.78 (t, J=8.4 Hz, 1H), 4.85 (brs, 2H); MS (ESI) m/z: 257.0 (M+H+).
66%		To a suspension of 2,4-difluoro-5-nitrophenol (1.01 g, 5.77 mmol) in EtOAc was added palladium hydroxide (0.08 g, 0.57 mmol) and the resulting slurry was stirred under a hydrogen atmosphere for 6h. The mixture was filtered through a Celite pad, washing with EtOAc (2x10 mL) and the filtrate was concentrated to afford 5-amino-2,4- difluorophenol (0.8 g, 96% yield) as a solid. FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO-i/6) delta 9.28 (s, 1H), 6.91 (t, J = 7.2 Hz, 1H), 6.35 (t, J = 8.8 Hz, 1H), 4.84 (brs, 2H); MS (ESI) m/z: 146.0 (M+H+). [00226] To a solution of <strong>[113512-71-3]5-amino-2,4-difluorophenol</strong> (0.3 g, 2.07 mmol) in DMSO (2 mL) was added potassium t-butoxide (0.23 g, 2.07 mmol) at RT. After stirring for lh, 3,5-dichloropyridine (0.37 g, 2.5 mmol) and potassium carbonate (0.14 g, 1 mmol) were added and the mixture was heated to 190 C for lh in microwave reactor. Water (30 mL) was added, and the product was extracted with EtOAc (2x35 mL) and the combined organic layers were washed with brine solution, dried (Na2SC>4), concentrated in vacuo and purified by chromatography (EtOAc/hexane) to afford 5-(5-chloropyridin-3-yloxy)- 2,4-difluorobenzenamine (0.35 g, 66% yield) as a solid. FontWeight="Bold" FontSize="10" H NMR (400 MHz, Acetone-i 6) delta 8.33 - 8.30 (m, 2H), 7.44 (t, J = 2.4 Hz, 1H), 7.13 (t, J = 10.8 Hz, 1H), 6.78 (t, J = 8.4 Hz, 1H), 4.85 (brs, 2H); MS (ESI) m z: 257.0 (M+H+).

Reference： [1]Patent: US2008/90856,2008,A1 .Location in patent: Page/Page column 35
[2]Patent: WO2013/36232,2013,A2 .Location in patent: Paragraph 00226

4
[ 367-27-1 ]
[ 113512-71-3 ]