[ CAS No. 5417-63-0 ] {[proInfo.proName]}

Name: 5417-63-0|3-Aminonaphthalen-2-ol|97%
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Quality Control of [ 5417-63-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 5417-63-0 ]

CAS No. :	5417-63-0	MDL No. :	MFCD00004113
Formula :	C₁₀H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZHVPTERSBUMMHK-UHFFFAOYSA-N
M.W :	159.19	Pubchem ID :	79449
Synonyms :

Calculated chemistry of [ 5417-63-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.38
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.26
Log Po/w (XLOGP3) :	1.91
Log Po/w (WLOGP) :	2.14
Log Po/w (MLOGP) :	1.88
Log Po/w (SILICOS-IT) :	1.77
Consensus Log Po/w :	1.79

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.65
Solubility :	0.359 mg/ml ; 0.00225 mol/l
Class :	Soluble
Log S (Ali) :	-2.5
Solubility :	0.498 mg/ml ; 0.00313 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.13
Solubility :	0.119 mg/ml ; 0.000748 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 5417-63-0 ]

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 [ 5417-63-0 ]

* 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 [ 5417-63-0 ]
Downstream synthetic route of [ 5417-63-0 ]

[ 5417-63-0 ] Synthesis Path-Upstream 1~10

1
[ 32361-60-7 ]
[ 5417-63-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5110 - 5118

2
[ 92-44-4 ]
[ 5417-63-0 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 496
[2] Chemische Berichte, 1894, vol. 27, p. 763
[3] Patent: DE117471, , ,

3
[ 608515-85-1 ]
[ 5417-63-0 ]

Reference： [1] Chemische Berichte, 1925, vol. 58, p. 2850

4
[ 412036-46-5 ]
[ 5417-63-0 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 373,375

5
[ 6962-30-7 ]
[ 5417-63-0 ]

Reference： [1] Chemische Berichte, 1925, vol. 58, p. 2850
[2] Chemische Berichte, 1925, vol. 58, p. 2850

6
[ 5341-58-2 ]
[ 5417-63-0 ]

Reference： [1] Chemische Berichte, 1925, vol. 58, p. 2850
[2] Chemische Berichte, 1925, vol. 58, p. 2850

7
[ 883-62-5 ]
[ 5417-63-0 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 373,375

8
[ 58698-35-4 ]
[ 5417-63-0 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 373,375

9
[ 7147-28-6 ]
[ 5417-63-0 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 373,375

10
[ 5417-63-0 ]
[ 771-97-1 ]

Reference： [1] Helvetica Chimica Acta, 1937, vol. 20, p. 520,524

[ 5417-63-0 ] Synthesis Path-Downstream 1~25

1
[ 57267-03-5 ]
[ 5417-63-0 ]
2,3-Dihydro-naphtho[2,3-d]oxazole-2-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Synthetic Communications,1984,vol. 14,p. 947 - 954

2
[ 51076-95-0 ]
[ 5417-63-0 ]
[ 41014-41-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	In ethanol
	In ethanol

Reference： [1]Mylari, Banavara L.; Scott, Pamela J.; Zembrowski, William J. [Synthetic Communications, 1989, vol. 19, # 16, p. 2921 - 2924]
[2]Mylari; Beyer; Scott; Aldinger; Dee; Siegel; Zembrowski [Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 457 - 465]

3
[ 605-70-9 ]
[ 5417-63-0 ]
Naphthalene-1,4-dicarboxylic acid bis-[(3-hydroxy-naphthalen-2-yl)-amide] [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1982,p. 1423 - 1433

4
[ 636-94-2 ]
[ 5417-63-0 ]
2,5-bis(2-naphth<2,3-d>oxazolyl)phenol [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 1613 - 1622

5
[ 610-22-0 ]
[ 5417-63-0 ]
[ 640295-90-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4125 - 4128

6
[ 21524-39-0 ]
[ 5417-63-0 ]
1-cyanobenzo[b]phenoxazine [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 385 - 390

7
[ 60835-75-8 ]
[ 5417-63-0 ]
[ 1004519-68-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃;

Reference： [1]Costero, Ana M.; Rodríguez-Muñiz, Gemma M.; Gil, Salvador; Peransi, Sergio; Gaviña, Pablo [Tetrahedron, 2008, vol. 64, # 1, p. 110 - 116]

8
[ 24415-66-5 ]
[ 5417-63-0 ]
3-(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamino)naphthalen-2-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3649 - 3653

9
[ 112-26-5 ]
[ 5417-63-0 ]
[ 1280220-16-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 6h;	3-Amino-2-naphthol (1.05 g, 6.6 mmol), 1,8-dichloro-3,6-dioxaoctane (0.5 mL, 3.3 mmol), and K2CO3 (1.4 g) in DMF (2 mL) were heated at 130 C for 6 h. After water addition, crude product was precipitated. Pure product was obtained with the use of column chromatography with the mixture of methylene chloride-acetone (20:1) as an eluent. Yield 0.6 g (42%) of the same product as in the route A.

Reference： [1]Tetrahedron,2011,vol. 67,p. 1862 - 1872

10
[ 55244-11-6 ]
[ 5417-63-0 ]
[ 1314518-63-2 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 3421 - 3429

11
[ 6948-30-7 ]
[ 5417-63-0 ]
[ 109-77-3 ]
[ 1375352-78-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol at 80℃; for 24h;	37 Example 37:3,5-Diamino-l-(3-bromo-4,5-dimethoxy-phenyl)-lH-benzo[f\|chromene-2-carbonitrile (37)(37) 3-Aminonaphthol (700.5 mg, 4.4 mmol), 5-bromo-3,4-dimethoxy-benzaldehyde (1.077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 μ, 1.46 mmol) and then stirred at 80 °C under LC-MS control for 24 h. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and the precipitates were collected by filtration, washed well with 50 % aqueous ethanol and dried under vacuum to yield the title compound ( 1.55 g, 3.43 mmol, 78 %).

Reference： [1]Current Patent Assignee: HEIDELBERG UNIVERSITY; Helmholtz Association - WO2012/62901, 2012, A2 Location in patent: Page/Page column 55-56

12
[ 10373-78-1 ]
[ 5417-63-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: Camphorquinone; 3-Amino-2-naphthol In ethanol for 2h; Reflux; Stage #2: With air In ethyl acetate at 20℃; for 76h; Reflux;

Reference： [1]Nowicka-Scheibe, Joanna [Synthetic Communications, 2013, vol. 43, # 16, p. 2198 - 2207]

13
[ 17261-28-8 ]
[ 5417-63-0 ]
C₂₉H₂₀NOP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In toluene at 150℃; for 15h; Inert atmosphere;	2.1. Synthesis of 2-(2-(diphenylphosphoryl)phenyl)naphtho[2,3-d]oxazole (2-PPN) 3-Amino-2-naphthol (0.159 g, 1.0 mmol), 2-(diphenylphosphino)benzoic acid (0.306 g,1.0 mmol) and p-toluene sulfonic acid (0.190 g, 1.0 mmol) were added to toluene (30 mL).The mixture was heated to 150C for 15 hr under nitrogen. The progress of reaction wasmonitored by TLC. After the reaction mixture cooled, the solution was extracted withwater, and the organic solution was evaporated. Then the crude intermediate in 10 mLdichloromethane were stirred in a round-bottom flask, and then H2O2 (1.2 mL, 10 mmol,30%) was slowly added into the mixture while stirring at room temperature. The organic layer was separated and washed with water. The extract was evaporated to dryness affordinga pale yellow solid. The residue was dissolved in CHCl3 and added to methanol in orderto get solid precipitate. The crude product was purified by column chromatography withCHCl3: ethyl acetate (5:1) eluent to afford pale yellow solid (0.222 g, yield 50%).
	With toluene-4-sulfonic acid In toluene at 150℃; for 15h; Inert atmosphere;	1 After dissolving 3-amino-2-naphthol (0.159 g, 1.0 mmol), 2 (diphenylphosphino) benzoic acid (0.306 g, 1.0 mmol) and paratoluenesulfonicacid (0.190 g, 1.0 mmol) in 30 ml of toluene,The mixture was stirred at 150 under N2 (g) air flow for 15 hours.The product was separated into H2O and toluene layers using H2O,after toluene layer only collected separately dissolved in minimum amount of CHCl3 and the solvent evaporated in evaporator was performed by a silica gel column (Merck 60, 70-230 mesh).The column was prepared using a solution of CHCl3: ethyl acetate in a volume ratio of 5: 1 (v: v),The extracted product was recrystallized with CHCl3 and ethyl acetate in a volume ratio of 5: 2. The recrystallized product was dissolved in 10 ml of CH2Cl2,While stirring, 2 ml of H2O2 (30%) was slowly added dropwise and the reaction was allowed to proceed overnight.The product was separated into a H2O layer and a CH2Cl2 layer using H2O,The CH2Cl2 layer alone was collected and the solvent was evaporated by evaporator and 2- (2-diphenylphosphoryl) phenyl) naphtho [2,3-d] oxazole (2-PPN),obtained.
	With toluene-4-sulfonic acid In toluene at 150℃; for 15h; Inert atmosphere;	2.3.1. 2-(2-(diphenylphosphoryl)phenyl)naphtho[2,3-d]oxazole (2-PPN) Figure 1 shows the synthetic scheme for 2-PPN. Thesynthesis of the PPN derivatives followed closely related procedures.11 12 After 3-amino-2-naphthol (0.159 g,1.0 mmol), 2-(diphenylphosphino)benzoic acid (0.306 g,1.0 mmol) and p-toluenesulfonic acid (0.190 g, 1.0 mmol)were dissolved in 30 ml toluene, the mixture was stirredfor 15 hours at 150 C under an N2 atmosphere in around bottom flask. The reaction progress was monitored via TLC. After cooling to ambient temperature, the mixturewas extracted with toluene, and the organic solutionwas collected and evaporated. Then the crude intermediatewas stirred in 10 mL CH2 Cl2, and then H2 O2 (1.2 mL,10 mmol, 30%) was added drop-wise while stirring atroom temperature. The organic solution was separatedand washed with deionized water, and the extract wasevaporated to dryness, affording to a pale yellow solid.This residue was dissolved in CHCl3 and was addedto methanol in order to obtain a solid precipitate. Thecrude product was chromatographed on silica gel withCHCl3:ethyl acetate, 5:1 to obtain pure 2-PPN.Anal.Calc.(%) for C29H20NO2P, C:78.19, H:4.53,N:3.14, O:7.18. Found (%, XPS) C:77.93, H:4.69, N:2.95,O:6.46. 1H-NMR (500 MHz, CDCl3, ppm) 8.18-8.21(m, 2H), 7.99 (s, 1H), 7.90 (q, = 11.5 Hz, 1H), 7.78-7.82 (m, 4H), 7.73-7.76 (m, 4H), 7.62 (q, =7.5 Hz, 1H),7.42-7.47 (m, 6H), 7.43 (s, 1H). 13C-NMR (125 MHz,CDCl3, ppm) 164.02, 149.22, 141.18, 135.37, 135.29,133.66, 133.25, 132.89, 132.40, 132.04, 131.71, 131.67,131.60, 131.59, 131.48, 131.46, 131.26, 131.03, 130.98,130.93, 130.84, 128.26, 128.17, 125.41, 124.55, 117.61,106.57. FT-IR (KBr, cm-1 1549 (C N), 1456 (P-C),1435 (aromatic C C), 1190 (stretch P O), 1113 (C-O).

Reference： [1]Kim, Ik-Hwan; Kang, Eunguk; Kim, Dong-Eun; Shin, Hoon-Kyu; Lee, Burm-Jong [Molecular Crystals and Liquid Crystals, 2014, vol. 597, # 1, p. 88 - 94]
[2]Current Patent Assignee: INJE UNIVERSITY - KR101581821, 2015, B1 Location in patent: Paragraph 0030-0031
[3]Kim, Ik-Hwan; Kim, Kyeong Hyeon; Jo, Hyunhee; Lee, Burm-Jong; Kim, Dong-Eun; Shin, Hoon-Kyu [Journal of Nanoscience and Nanotechnology, 2017, vol. 17, # 5, p. 3298 - 3303]

14
[ 17282-03-0 ]
[ 201230-82-2 ]
[ 5417-63-0 ]
3-methylnaphtho[2,3-b]pyrido[3,2-f ][1,4]oxazepin-5(6H)-one [ No CAS ]

Reference： [1]Catalysis Science and Technology,2015,vol. 5,p. 4433 - 4443

15
[ 17028-61-4 ]
[ 5417-63-0 ]
C₁₈H₁₄N₂O₅ [ No CAS ]

Reference： [1]CrystEngComm,2016,vol. 18,p. 704 - 713

16
[ 5417-63-0 ]
[ 109-77-3 ]
[ 112641-20-0 ]
3,5-diamino-1-(2-fluoro-3-trifluoromethylphenyl)-1H-benzo[f]chromene-2-carbonitrile [ No CAS ]

Reference： [1]EXCLI Journal,2017,vol. 16,p. 868 - 902

17
[ 25952-53-8 ]
[ 5417-63-0 ]
N-ethylnaphtho[2,3-d]oxazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In isopropyl alcohol; at 80℃; for 0.25h;Microwave irradiation;	General procedure: A mixture of o-phenylenediamine (1.0 mmol) and EDC.HCl (1.1 mmol) in 2-propanol (10 mL) was irradiated in microwave apparatus at 200 W (80 C) for 15 min. The reaction was monitored by TLC (eluent CH2Cl2 / MeOH 95:5). After completion, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 25 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure and the obtained crude product was purified by flash column chromatography using silica gel (100-200 mesh) with 1-5% MeOH/CH2Cl2 as eluent. The fractions containing product were collected and concentrated under reduced pressure to afford N-ethyl-1Hbenzo[d]imidazol-2-amine (1a, 90% yield) as an off white solid.

Reference： [1]Synthetic Communications,2019,vol. 49,p. 1308 - 1315

18
[ 2273-45-2 ]
[ 90-02-8 ]
[ 5417-63-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
92%	In methanol; toluene for 12h; Reflux; Dean-Stark;	2.4.1. 10,10-Di-methyl-1-aza-10-stanna-9,11-dioxapentacycle[8.11.0.01,80.12,21]henicosa-1,3,5,7,13,15,17,19-nonaene (1a) General procedure: Compound 1a was synthesized as follow: a solution of 3-amino-2-napthol 0.05 g (0.31 mmol), salicylaldehyde 0.038 g (0.31 mmol) anddimethyltin oxide 0.051 g (0.31 mmol) was solved in a solvent mixturetoluene/methanol (4:1/v:v) (50 mL), heated under reflux for 12 h usinga Dean-Stark tramp for removal of water as azeotropic mixture, thensolution was allowed to cool to room temperature. The solvent mixturewas removed under vacuum, after work-up compound 1a was isolated as red solid with 92% yield (0.1185 g). M.p. 163-166 °C. FTIR νmax(ATR): 1620 (C]N), 566 (SneC), 550 (SneO) cm-1. IE+ MS, m/z (%):411 (M+, 68), 396 (M+-Me), 5), 381 (M+-2Me), 100). 1H NMR(300 MHz, CDCl3) δ: 8.83 (2H, s, 3JSn-H=47.6 Hz, H-7), 7.72 (1H, s, H-17), 7.68 (1H, d, J=8.2 Hz, H-14), 7.58 (1H, d, J=8.2 Hz, H-13), 7.43(1H, td, J=8.6, 1.7 Hz, H-15,16), 7.31 (ddd, J=8.2, 7.0, 1.1 Hz, H-4),7.19 (1H, td, J=8.0, 1.1 Hz, H-3), 7.08 (1H, s, H-10), 6.80 (1H, d,J=8.6 Hz, H-6), 6.78 (1H, td, J=7.8, 0.9 Hz, H-5), 0.79 (6H, s, Me 2J(119/117Sn-1H)=77.9/74.6 Hz) ppm. 13C NMR (75 MHz, CDCl3) δ:170.0 (C-1), 164.5 (C-7), 156.4 (C-9), 137.8 (C-4), 135.8 (C-8, C-3),134.4 (C-11), 127.9 (C-14), 126.6 (C-12, 16), 126.1 (C-17), 123.0 (C-15), 122.9 (C-6), 118.1 (C-2), 117.6 (C-5), 113.4 (C-13, 3J(119/Sn-13C)=18 Hz), 111.1 (C-10, 3J(119Sn-13C)=9.0 Hz) 1.14 (Me 1J(119/117Sn-13C)=660/631 Hz) ppm. 119Sn NMR (112.0 MHz, CDCl3) δ:-142 ppm. HRMS (IE+): m/z [M]+ Calc. for C19H17NO2Sn: 411.0281;Found: 411.0286.Compounds 1b-1r were synthesized following a similar strategy asfor compound 1a, only time reactions were changed which are describedat Supplementary Material.