[ CAS No. 155020-51-2 ] {[proInfo.proName]}

Name: 155020-51-2|2,3-Difluoro-4-methoxyaniline|98%
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Quality Control of [ 155020-51-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 155020-51-2 ]

SDS Specification

Alternatived Products of [ 155020-51-2 ]

Product Details of [ 155020-51-2 ]

CAS No. :	155020-51-2	MDL No. :	MFCD04115986
Formula :	C₇H₇F₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MEETZAMYCFAKKW-UHFFFAOYSA-N
M.W :	159.13	Pubchem ID :	3798495
Synonyms :

Calculated chemistry of [ 155020-51-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.25
TPSA :	35.25 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) :	-6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.62
Log Po/w (XLOGP3) :	1.41
Log Po/w (WLOGP) :	2.4
Log Po/w (MLOGP) :	2.02
Log Po/w (SILICOS-IT) :	1.95
Consensus Log Po/w :	1.88

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.05
Solubility :	1.41 mg/ml ; 0.00886 mol/l
Class :	Soluble
Log S (Ali) :	-1.75
Solubility :	2.8 mg/ml ; 0.0176 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.71
Solubility :	0.309 mg/ml ; 0.00194 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.38

Safety of [ 155020-51-2 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P322-P330-P332+P313-P337+P313-P340-P361-P362-P363-P403-P403+P233-P405-P501	UN#:	2811
Hazard Statements:	H302-H311-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 155020-51-2 ]

* 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.

Downstream synthetic route of [ 155020-51-2 ]

[ 155020-51-2 ] Synthesis Path-Downstream 1~41

1
[ 66684-59-1 ]
[ 155020-51-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With palladium on activated charcoal; hydrogen; In methanol; for 4.5h;	Degussa grade Pd/C (1.125 g, 1.058 mmol) was added to a 250 mL round bottom flask previously purged with argon. The Pd was carefully wetted with a few milliliters ofMeOH before the full amount of solvent (42.3 ml) was added. The head space of the flask was evacuated until the solvent began to slightly bubble and then back-filled 3x with N2. <strong>[66684-59-1]2,3-difluoro-1-methoxy-4-nitrobenzene</strong> (2.0 g, 10.58 mmol) was added to the black suspension, and a balloon of H2 gas was attached. The heterogeneous mixture was sparged with H2 for 30 mm, before being allowed to stir under an atmosphere of H2 for anadditional 4 h. The reaction mixture was then filtered over celite to remove Pd/C. The177celite was rinsed with EtOAc, and the filtrate was concentrated to afford Intermediate I-41A(1.63g, 10.24 mmol, 97 %yield) as a purple solid. LC-MS: Method H, RT = 0.83 mm, MS (ESI) m/z: 160.1 (M+H) ?H NMR (400MHz, CHLOROFORM-d) 6.59 (td, J=8.6, 2.2 Hz, 1H), 6.49-6.43 (m, 1H), 3.83 (s, 3H), 3.51 (br. s., 2H).
90%	With hydrogenchloride; tin(ll) chloride; In ethanol; water; ethyl acetate; at 20.0℃; for 16.0h;	2, 3-Difluoro-4-methoxyaniline To a mixture of <strong>[66684-59-1]2,3-difluoro-1-methoxy-4-nitrobenzene</strong> 1 (1 equiv.) in EtOH (0.5 M) was added SnCl2 (5 equiv.). Then HCl (25 mL) was added and the reaction was stirred at room temperature for 16 h. Ethyl acetate and H2O were added, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, and filtered, then the filtrate was concentrated in vacuo to give 2, 3-difluoro-4-methoxyaniline (90%) as a brown solid.
	With iron; ammonium chloride; In ethanol; water; at 80.0℃; for 4.0h;	Step 1 Preparation of Compound a2 (0413) Compound a1 (3.0g, 16mmol) was dissolved in ethanol (30mL) and water (10mL), and iron (2.7g, 48 mmol) and ammonium chloride (2.6g, 48mmol) were added into the reaction mixture, the reaction mixture was stirred at 80 C for 4 hours. The mixtures are filtered, and water was added into the mother liquor. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The organic layer was condensed under reduced pressure to afford Compound a2 (2.5g) as crude. [M+H]=159.6, Method Condition 4 : retention time 1.07 min

Reference： [1]Patent: WO2018/13774,2018,A1 .Location in patent: Page/Page column 177; 178
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 1362 - 1370
[3]Patent: US2016/96841,2016,A1 .Location in patent: Paragraph 0308
[4]Patent: EP3059225,2016,A1 .Location in patent: Paragraph 0413

2
[ 108-24-7 ]
[ 155020-51-2 ]
[ 155020-52-3 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1362 - 1370

3
[ 771-69-7 ]
[ 155020-51-2 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1362 - 1370

4
[ 155020-51-2 ]
[ 155020-53-4 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1362 - 1370

5
[ 155020-51-2 ]
[ 1026596-14-4 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1362 - 1370

6
[ 155020-51-2 ]
[ 155020-46-5 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1362 - 1370

7
[ 155020-51-2 ]
7-chloro-4-<3'-<(diethylamino)methyl>-5',6'-difluoro-4'-hydroxyanilino>quinoline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1362 - 1370

8
[ 155020-51-2 ]
7-chloro-4-<3'-<(diethylamino)methyl>-2',6'-difluoro-4'-hydroxyanilino>quinoline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1362 - 1370

9
[ 155020-51-2 ]
4-Amino-6-diethylaminomethyl-2,3-difluoro-phenol; hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1362 - 1370

10
[ 155020-51-2 ]
[ 940298-94-2 ]

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 1256 - 1260

11
[ 393-55-5 ]
[ 155020-51-2 ]
[ 1138820-03-7 ]

Yield	Reaction Conditions	Operation in experiment
86%		As shown in step 1-i of Scheme 1,<strong>[393-55-5]2-fluoronicotinic acid</strong> (8.5 g, 59.0 mmol) was suspended in 100 mL of anhydrous dichloromethane and 0.274 mL of anhydrous DMF. The mixture was cooled to 5C with an ice bath. Oxalyl chloride (5.41 mL, 62.0 mmol) was added dropwise to the cooled mixture. After addition, the mixture was warmed to room temperature and stirred for 15 hours, at which time all solids had gone into solution. The mixture was cooled to 00C and 2,3-difluoro-4-methoxyaniline (Compound 1001, 10.0 g, 62.84 mmol) in 30 mL of DCM was added dropwise. Followed by the dropwise addition of DIEA (20.6 mL, 118.1 mmol). The mixture was warmed to room temperature and stirred for 16 hours, after which time the reaction was quenched with 60 mL of 2M HCl. The organics were washed twice with 50 mL of saturated sodium bicarbonate, once with 50 mL of water, and once with 50 mL of brine. The organics were then dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The residue was slurried in 350 mL of hexanes, stirred for 30 minutes, collected by vacuum filtration, washed well with hexanes, and dried under vacuum to afford 2-fluoro-N-(2,3-difluoro-4-methoxyphenyl)pyridine-3- carboxamide (Compound 1002, 14.3 g, 86% yield): 1H NuMR (300 MHz, CDCl3) delta 8.68 - 8.62 (m, 2H), 8.40 (dt, J = 4.7, 1.6 Hz, IH), 8.06 - 7.99 (m, IH), 7.44 (td, J = 5.0, 2.5 Hz, IH), 6.82 - 6.75 (m, IH) and 3.91 (d, J = 5.4 Hz, 3H).

Reference： [1]Patent: WO2010/48131,2010,A1 .Location in patent: Page/Page column 49-50

12
[ 155020-51-2 ]
4-fluoro-5-isopropyl-2-methoxy-3-(4-methylpiperazin-1-yl)-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/127629,2015,A1

13
[ 155020-51-2 ]
methyl 6-cyano-2-((2,3-difluoro-4-methoxyphenyl)-(isopropyl)amino)-1H-indole-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/127629,2015,A1
[2]Patent: WO2018/94134,2018,A1

14
[ 155020-51-2 ]
3,4-difluoro-5-isopropyl-2-methoxy-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/127629,2015,A1
[2]Patent: WO2018/94134,2018,A1

15
[ 155020-51-2 ]
4-fluoro-5-isopropyl-2-methoxy-3-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/127629,2015,A1

16
[ 155020-51-2 ]
5-cyclobutyl-4-fluoro-2-methoxy-3-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-indolo [2,3-b]quinoline-8-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/127629,2015,A1

17
[ 155020-51-2 ]
5-cyclobutyl-3,4-difluoro-2-methoxy-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/127629,2015,A1

18
[ 155020-51-2 ]
methyl 6-cyano-2-(cyclobutyl(2,3-difluoro-4-methoxyphenyl)amino)-1H-indole-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/127629,2015,A1

19
[ 155020-51-2 ]
5-cyclobutyl-4-fluoro-2-methoxy-3-(4-methylpiperazin-1-yl)-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/127629,2015,A1

20
[ 1191-95-3 ]
[ 155020-51-2 ]
N-cyclobutyl-2,3-difluoro-4-methoxyaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 12h;	Cyclobutanone (14.0 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of <strong>[155020-51-2]2,3-difluoro-4-methoxyaniline</strong> (3.18 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT overnight. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford N-cyclobutyl-<strong>[155020-51-2]2,3-difluoro-4-methoxyaniline</strong> (3.82g, 90% yield).MS m/z= 214 [M+H].

Reference： [1]Patent: WO2015/127629,2015,A1 .Location in patent: Page/Page column 105; 106

21
[ 67-64-1 ]
[ 155020-51-2 ]
2,3-difluoro-N-isopropyl-4-methoxyaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 12h;	Acetone (11.6 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of <strong>[155020-51-2]2,3-difluoro-4-methoxyaniline</strong> (3.18 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford 2,3-difluoro-N-isopropyl-4-methoxyaniline. (2.8 g, 70% yield). 1H NMR (400 MHz, CDC13) δ ppm 6.65 (td, J= 8.7, 2.3 Hz, 1H), 6.39 (td, J= 8.7, 2.3 Hz, 1H), 3.85 (s, 3H), 3.58-3.56 (m, 1H), 3.46 (s, 1H), 1.24 (d, J= 6.2 Hz, 6H).
70%	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 12h;	[0154] Acetone (11.6 g, 200 mmol), acetic acid (1.8 g, 30 mmol), and sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of 2,3-difluoro-4- methoxyaniline (3.18 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at room temperature (RT) for 12 h. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography with hexane/ethyl acetate (9/1, v/v) to afford the title compound (2.8 g, 70% yield). 1H NMR (400 MHz, CDC13) δ ppm 6.65 (td, 7 = 8.7, 2.3 Hz, 1H), 6.39 (td, 7 = 8.7, 2.3 Hz, 1H), 3.85 (s, 3H), 3.58-3.56 (m, 1H), 3.46 (s, 1H), 1.24 (d, 7 = 6.2 Hz, 6H).

Reference： [1]Patent: WO2015/127629,2015,A1 .Location in patent: Page/Page column 96; 97
[2]Patent: WO2018/94134,2018,A1 .Location in patent: Paragraph 0153-0154

22
[ 7188-38-7 ]
[ 100-52-7 ]
[ 155020-51-2 ]
[ 637-44-5 ]
C₂₈H₂₆F₂N₂O₃ [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1040 - 1043

23
[ 155020-51-2 ]
(1s,4s)-4-(8-(2,3-difluoro-4-methoxyphenylamino)-2-(tetrahydro-2H-pyran-4-ylamino)-9H-purin-9-yl)cyclohexanecarboxamide [ No CAS ]

Reference： [1]Patent: US2016/96841,2016,A1

24
[ 463-71-8 ]
[ 155020-51-2 ]
2,3-difluoro-1-isothiocyanato-4-methoxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2h;	2,3-Difluoro-1-isothiocyanato-4-methoxybenzene To a solution of <strong>[155020-51-2]2,3-difluoro-4-methoxyaniline</strong> (1 equiv.) in DCM (0.8 M) was added DIEA (2.5 equiv.) at 0 C., then SCCl2 (5 equiv.) was added drop-wise at 0 C. The reaction mixture was stirred at room temperature for 2 h. The organic solvent was condensed in vacuo and purified via silica gel to give 2,3-difluoro-1-isothiocyanato-4-methoxybenzene (94%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 7.42-7.27 (m, 1H), 7.08 (dt, J=2.1, 8.9 Hz, 1H), 3.99-3.83 (m, 3H).

Reference： [1]Patent: US2016/96841,2016,A1 .Location in patent: Paragraph 0309

25
[ 79-31-2 ]
[ 155020-51-2 ]
C₁₁H₁₃F₂NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃;Cooling with ice;	Step 2 Preparation of Compound a3 (0414) Compound a2 (2.5g, 16mmol) was dissolved in DMF (30mL), and isobutyric acid (1.7g, 19 mmol) ant · O-(7-Azabenzotriazol-1-yl)-1, 1, 3, -tetramethyluronium hexafluorophosphate (7.8g, 21mmol) and triethyl amine (3.1g, 32mmol) was added to the reaction mixture while cooling in ice. The reaction mixture was stirred at room temperature overnight. Water was added into the mixture and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was condensed under reduced pressure to afford Compound a3 (5.1g) as crude. [M+H]=229.8, Method Condition 4 : retention time 1.54 min

Reference： [1]Patent: EP3059225,2016,A1 .Location in patent: Paragraph 0414

26
[ 155020-51-2 ]
C₁₉H₂₁FN₄O₄ [ No CAS ]

Reference： [1]Patent: EP3059225,2016,A1

27
[ 155020-51-2 ]
C₁₁H₁₂FNO₂ [ No CAS ]

Reference： [1]Patent: EP3059225,2016,A1

28
[ 155020-51-2 ]
C₁₀H₁₀FNO₂ [ No CAS ]

Reference： [1]Patent: EP3059225,2016,A1

29
[ 1147550-11-5 ]
[ 155020-51-2 ]
4,5-difluoro-6-methoxybenzo[d]thiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%		To a solution of Intermediate I-41A (1.63g, 10.24 mmol) in acetonitrile (51.2 ml) was added ammoniumthiocyanate (1.014 g, 13.32 mmol). The mixture was stirred atroom temperature for 10 mm followed by the addition of benzyltrimethylammonium tribromide (4.39 g, 11.27 mmol). After 16 h, the reaction mixture was concentrated down and retaken in DCM. The organic phase was washed with saturated NaHCO3, concentrated and purified by ISCO (120g, 0-100% EtOAc/Hexanes, 16 mm. Product from 55%-100%) to afford Intermediate I-41B (398mg, 1.843 mmol, 18 % yield).LC-MS: Method H, RT = 0.93 mm, MS (ESI) mlz: 217.2 (M+H) ‘H NMR (400MHz, CHLOROFORM-d) 6.96 (dd,J=6.9, 2.1 Hz, 1H), 5.19 (br. s., 2H), 3.92 (s, 3H).

Reference： [1]Patent: WO2018/13774,2018,A1 .Location in patent: Page/Page column 178

30
[ 155020-51-2 ]
4-fluoro-5-isopropyl-2-methoxy-11-oxo-3-((3R,5S)-3,4,5-trimethylpiperazin-1-yl)-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]