[ CAS No. 3846-73-9 ] {[proInfo.proName]}

Name: 3846-73-9|4-Methylquinolin-8-ol|96%
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Quality Control of [ 3846-73-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 3846-73-9 ]

CAS No. :	3846-73-9	MDL No. :	MFCD02170459
Formula :	C₁₀H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OYUKRQOCPFZNHR-UHFFFAOYSA-N
M.W :	159.19	Pubchem ID :	345169
Synonyms :

Calculated chemistry of [ 3846-73-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.1
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.73
TPSA :	33.12 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) :	-5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.89
Log Po/w (XLOGP3) :	2.41
Log Po/w (WLOGP) :	2.25
Log Po/w (MLOGP) :	1.49
Log Po/w (SILICOS-IT) :	2.44
Consensus Log Po/w :	2.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.96
Solubility :	0.174 mg/ml ; 0.00109 mol/l
Class :	Soluble
Log S (Ali) :	-2.75
Solubility :	0.285 mg/ml ; 0.00179 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.5
Solubility :	0.0503 mg/ml ; 0.000316 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.08

Safety of [ 3846-73-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3846-73-9 ]

* 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 [ 3846-73-9 ]
Downstream synthetic route of [ 3846-73-9 ]

[ 3846-73-9 ] Synthesis Path-Upstream 1~6

1
[ 78-94-4 ]
[ 95-55-6 ]
[ 3846-73-9 ]

Yield	Reaction Conditions	Operation in experiment
27.5%	With hydrogenchloride In water at 120℃; for 6 h;	Hydrochloric acid (37percent, 45.5 ml) and 2-aminophenol (10.91 g, 0.1 mol) were put into a 250 ml two-necked round flask, mixed thoroughly and heated to 120 °C. The mixture was added methyl vinyl ketone (14.32 ml, 0.175 mol) dropwise and reflux for 6 h. After being cooled to room temperature, the mixture was neutralized with aqueous sodium hydroxide solution and then extracted with dichloromethane (CH₂Cl₂) (50 ml × 3). The solution was dried with anhydrous MgSO₄ and then the solvent was removed on a rotary evaporator. The crude product was further purified by column chromatography (silica gel) with CH₂Cl₂as the eluent, followed by a recrystallization in the mixture of CH₂Cl₂ and n-hexane (1:1, v/v) to give a colorless solid (4.38 g, yield 27.5percent). δ_H (400 MHz; (CD₃)₂CO; Me₄Si): 8.68 (d, 1H, J=4.4 Hz), 7.55 (dd, 1H, J₁=8.4 Hz, J₂=1.5 Hz), 7.51 (dd, 1H, J₁=8.4 Hz, J₂=7.2 Hz), 7.41 (dd, 1H, J₁=4.4 Hz, J₂=0.8 Hz), 7.12 (dd, 1H, J₁=7.2 Hz, J₂=1.5 Hz), 2.71 (d, 3H, J=0.8 Hz).

Reference： [1] Chemical Communications, 2015, vol. 51, # 84, p. 15458 - 15461
[2] Journal of the Chinese Chemical Society, 2004, vol. 51, # 4, p. 735 - 742
[3] Tetrahedron Letters, 2016, vol. 57, # 25, p. 2797 - 2799
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 3986
[5] Patent: US4843082, 1989, A,
[6] Patent: US2014/296251, 2014, A1, . Location in patent: Paragraph 0246 - 0248
[7] Patent: WO2014/163622, 2014, A1, . Location in patent: Page/Page column 34
[8] Patent: TWI543969, 2016, B, . Location in patent: Page/Page column 52
[9] Journal of Fluorescence, 2018, vol. 28, # 5, p. 1121 - 1126

2
[ 18826-95-4 ]
[ 95-55-6 ]
[ 826-81-3 ]
[ 3846-73-9 ]

Reference： [1] Russian Journal of General Chemistry, 2016, vol. 86, # 7, p. 1613 - 1618[2] Zh. Obshch. Khim., 2016, vol. 86, # 7, p. 1135 - 1140,6

3
[ 61703-95-5 ]
[ 3846-73-9 ]

Reference： [1] Patent: US2005/10048, 2005, A1, . Location in patent: Page/Page column 41
[2] Organometallics, 2010, vol. 29, # 6, p. 1465 - 1471

4
[ 90-04-0 ]
[ 78-94-4 ]
[ 3846-73-9 ]

Reference： [1] Tetrahedron, 1996, vol. 52, # 8, p. 2937 - 2944

5
[ 109-87-5 ]
[ 95-55-6 ]
[ 67-64-1 ]
[ 3846-73-9 ]

Reference： [1] Journal of the American Chemical Society, 1948, vol. 70, p. 410
[2] Acta Microbiologica Academiae Scientiarum Hungaricae, 1957, vol. 4, p. 279,280

6
[ 491-35-0 ]
[ 3846-73-9 ]

Reference： [1] Chemische Berichte, 1890, vol. 23, p. 2687

[ 3846-73-9 ] Synthesis Path-Downstream 1~59

1
[ 491-35-0 ]
[ 3846-73-9 ]

Reference： [1]Chemische Berichte,1890,vol. 23,p. 2687

2
[ 3846-73-9 ]
[ 100-39-0 ]
[ 101441-65-0 ]

Yield	Reaction Conditions	Operation in experiment
50.1%	With sodium hydroxide; In ethanol; at 80℃; for 20.0h;	<strong>[3846-73-9]4-methyl-8-hydroxyquinoline</strong> (3.18 g, 0.02 mol) and sodium hydroxide (1.60 g, 0.04 mol) were dissolved in ethanol (80 ml), mixed thoroughly and heated to 80 C. The mixture was added benzyl bromide (2.85 ml, 0.024 mol) dropwise and reflux for 20 h. After cooled to room temperature, the mixture was neutralized with dilute hydrochloric acid and then extracted with CH2Cl2. The solution was dried with anhydrous MgSO4 and then the solvent was removed on a rotary evaporator. The crude product was further purified by a column chromatography (silica gel) with CH2Cl2 as the eluent, giving a colorless solid (2.50 g, yield 50.1%). deltaH (400 MHz; CDCl3; Me4Si): 8.94 (d, 1H, J=4.5 Hz), 7.54-7.59 (m, 3H), 7.45 (t, 1H, J=8.0 Hz), 7.29-7.39 (m, 4H), 7.10 (d, 1H, J=8.0 Hz), 5.49 (s, 2H), 2.74 (s, 3H).
	With potassium hydroxide; In ethanol;Reflux;	The intermediate INT 1 was synthesized through ring closure from 2-aminophenol reacted with methyl vinyl ketone. INT 1 was reacted with various alkyl halides to afford 8-alkoxy-4methylquinoline derivatives as intermediates. Corresponding Rr(CH2)_,OH was reacted with intermediates to synthesize series of compounds J and I. The protective group J was removed by hydrogenation (method illustrated in example 1) to obtain compound K.
	With potassium hydroxide; In ethanol;Reflux;	Example 7 - Preparation of 8-hydroxyquino -yi) or (S-alkovyquino -yl) aikyl alcohols SWT 1 11 = 11-12 n = 11-12 K1 - K2 J1 - J2 Reagents and conditions: (a) methyl vinyl ketone, HCL reflux, (b) Mel. sCCh, acetone, rt 8h; Elf or 2~bromopropane or methylenecyclopropyl bromide, K2CO3, DMF, 60 6C, (c) I) LH.MDS, THF, 0 C, 1 h.: 2) Br(CH2)..i H, rt. (d) BnBr. KOM, EtOH, reflux, (e) H Pd/C, MeOH, rt 24 h. Method: Te intermediate INT was synthesized through ring closure from 2-arninophenol reacted with methyl vin l ketone. INT I was reacled with various aJkyl halides to afford 8-alkoxy- 4methylquino.)me derivatives as intermediates. Corresponding Brt'CHs iOH was reacted with intermediates to synthesize series of compounds 3 and I. The protective group J was removed by hydrogenaiiori (method iliustraied in example I) to obtain compound K. 1 1 -(S-nietlioxyquinoIin-4-yl)imde?aii-i-oI ( I) YD: 34%. lH NMR (400 MHz, CDt) 88.80 (ckt J - 4.4, 0.6 Hz. IH), 7.59 (dd, J ~ 8.4, 0.8 Hz, I H), 7.44-7.49 (m, 1H 7.03 (d. J - 7.6 Hz, Hh 4.08 (3, 3H); 3.63 ( J ::: 6.8 Hz, 2H), 3.03 (t J - 7.6 Hz, 2H), 1.74 (quia - 7.6 Hz, 2H), S .55 (quin, J - 7.2 Hz, 2H), 1.23-1.45 (br, 1SH); MS. m/z 329.9, JM+Hf .

With potassium hydroxide; In ethanol;Reflux;

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2797 - 2799
[2]Journal of the Chinese Chemical Society,2004,vol. 51,p. 735 - 742
[3]Helvetica Chimica Acta,1956,vol. 39,p. 1676,1680
[4]Patent: US2014/296251,2014,A1 .Location in patent: Paragraph 0246 - 0248
[5]Patent: WO2014/163622,2014,A1 .Location in patent: Page/Page column 34-35
[6]Patent: TWI543969,2016,B .Location in patent: Page/Page column 52

3
[ 3846-73-9 ]
[ 90-02-8 ]
[ 109093-26-7 ]

Reference： [1]Journal of Organic Chemistry,1959,vol. 24,p. 1104

4
[ 3846-73-9 ]
[ 121-33-5 ]
[ 109807-23-0 ]

Reference： [1]Journal of Organic Chemistry,1959,vol. 24,p. 1104

5
[ 3846-73-9 ]
8-hydroxy-4-methyl-quinoline-7-sulfonic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1948,vol. 70,p. 410

6
[ 78-94-4 ]
[ 95-55-6 ]
[ 3846-73-9 ]

Yield	Reaction Conditions	Operation in experiment
27.5%	With hydrogenchloride; In water; at 120℃; for 6.0h;	Hydrochloric acid (37%, 45.5 ml) and 2-aminophenol (10.91 g, 0.1 mol) were put into a 250 ml two-necked round flask, mixed thoroughly and heated to 120 C. The mixture was added methyl vinyl ketone (14.32 ml, 0.175 mol) dropwise and reflux for 6 h. After being cooled to room temperature, the mixture was neutralized with aqueous sodium hydroxide solution and then extracted with dichloromethane (CH2Cl2) (50 ml × 3). The solution was dried with anhydrous MgSO4 and then the solvent was removed on a rotary evaporator. The crude product was further purified by column chromatography (silica gel) with CH2Cl2 as the eluent, followed by a recrystallization in the mixture of CH2Cl2 and n-hexane (1:1, v/v) to give a colorless solid (4.38 g, yield 27.5%). deltaH (400 MHz; (CD3)2CO; Me4Si): 8.68 (d, 1H, J=4.4 Hz), 7.55 (dd, 1H, J1=8.4 Hz, J2=1.5 Hz), 7.51 (dd, 1H, J1=8.4 Hz, J2=7.2 Hz), 7.41 (dd, 1H, J1=4.4 Hz, J2=0.8 Hz), 7.12 (dd, 1H, J1=7.2 Hz, J2=1.5 Hz), 2.71 (d, 3H, J=0.8 Hz).
	With hydrogenchloride; sodium hydroxide;	(A) 4-Methyl-8-quinolinol A solution of 100 ml of concentrated hydrochloric acid, 27.3 g (250 mmol) of 2-aminophenol and 41 ml (500 mmol, 2 eq.) of methyl vinyl ketone was heated to 110-120 C. for 18 hours. The reaction was cooled, poured onto crushed ice, brought to pH 7 using 10N sodium hydroxide and extracted with ethyl acetate. The organic layers were washed with water, brine, dried (magnesium sulfate) and concentrated in vacuo. Purification by flash chromatography (silica gel, 1:2 ethyl acetate/petroleum ether) and crystallization (ethyl acetate) gave 5.3 g of the title compound as a light yellow solid: melting point 135-136 C.
	With hydrogenchloride;Reflux;	The intermediate INT 1 was synthesized through ring closure from 2-aminophenol reacted with methyl vinyl ketone. INT 1 was reacted with various alkyl halides to afford 8-alkoxy-4methylquinoline derivatives as intermediates. Corresponding Rr(CH2)_,OH was reacted with intermediates to synthesize series of compounds J and I. The protective group J was removed by hydrogenation (method illustrated in example 1) to obtain compound K.

With hydrogenchloride; In water;Reflux;

Example 7 - Preparation of 8-hydroxyquino -yi) or (S-alkovyquino -yl) aikyl alcohols SWT 1 11 = 11-12 n = 11-12 K1 - K2 J1 - J2 Reagents and conditions: (a) methyl vinyl ketone, HCL reflux, (b) Mel. sCCh, acetone, rt 8h; Elf or 2~bromopropane or methylenecyclopropyl bromide, K2CO3, DMF, 60 6C, (c) I) LH.MDS, THF, 0 C, 1 h.: 2) Br(CH2)..i H, rt. (d) BnBr. KOM, EtOH, reflux, (e) H FontWeight="Bold" FontSize="10" Pd/C, MeOH, rt 24 h. Method: Te intermediate INT was synthesized through ring closure from 2-arninophenol reacted with methyl vin l ketone. INT I was reacled with various aJkyl halides to afford 8-alkoxy- 4methylquino.)me derivatives as intermediates. Corresponding Brt'CHs iOH was reacted with intermediates to synthesize series of compounds 3 and I. The protective group J was removed by hydrogenaiiori (method iliustraied in example I) to obtain compound K. 1 1 -(S-nietlioxyquinoIin-4-yl)imde?aii-i-oI ( I) YD: 34%. lH NMR (400 MHz, CDt) 88.80 (ckt J - 4.4, 0.6 Hz. IH), 7.59 (dd, J ~ 8.4, 0.8 Hz, I H), 7.44-7.49 (m, 1H 7.03 (d. J - 7.6 Hz, Hh 4.08 (3, 3H); 3.63 ( J ::: 6.8 Hz, 2H), 3.03 (t J - 7.6 Hz, 2H), 1.74 (quia - 7.6 Hz, 2H), S .55 (quin, J - 7.2 Hz, 2H), 1.23-1.45 (br, 1SH); MS. m/z 329.9, JM+Hf .

Reference： [1]Chemical Communications,2015,vol. 51,p. 15458 - 15461
[2]Journal of the Chinese Chemical Society,2004,vol. 51,p. 735 - 742
[3]Tetrahedron Letters,2016,vol. 57,p. 2797 - 2799
[4]Journal of the American Chemical Society,1949,vol. 71,p. 3986
[5]Patent: US4843082,1989,A
[6]Patent: US2014/296251,2014,A1 .Location in patent: Paragraph 0246 - 0248
[7]Patent: WO2014/163622,2014,A1 .Location in patent: Page/Page column 34
[8]Patent: TWI543969,2016,B .Location in patent: Page/Page column 52
[9]Journal of Fluorescence,2018,vol. 28,p. 1121 - 1126

7
[ 109-87-5 ]
[ 95-55-6 ]
[ 67-64-1 ]
[ 3846-73-9 ]

Reference： [1]Journal of the American Chemical Society,1948,vol. 70,p. 410

8
[ 3846-73-9 ]
[ 62748-01-0 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 2937 - 2944
[2]Organometallics,2010,vol. 29,p. 1465 - 1471

9
[ 90-04-0 ]
[ 78-94-4 ]
[ 3846-73-9 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 2937 - 2944

10
[ 3846-73-9 ]
[ 19249-03-7 ]
1,10-Bis(4-methylquinolin-8-yl)-1,4,7,10-tetraoxadecane [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,1997,vol. 33,p. 1669 - 1673

11
[ 3846-73-9 ]
[ 108-24-7 ]
[ 104294-01-1 ]

Reference： [1]Synthesis,1999,p. 1819 - 1829

Yield	Reaction Conditions	Operation in experiment
		Examples of hydroxyl compounds which were used according to the invention are: ... 2-hydroxy-pyridine, 3-hydroxy-pyridine, 4-hydroxy-pyridine, 5-hydroxy-4-methyl-quinoline, 8-hydroxy-4-methyl-quinoline.
		The reaction was warmed to 0 C., stirred for 15 minutes and 0.30 g (1.9 mmol) of 4-methyl-8-quinolinol in 10 ml of dry tetrahydrofuran was added. The temperature was maintained at 0 C. for 24 hours, then the solution was warmed to room temperature and 3.0 ml (15 mmol, 8 eq.) of 1-bromononane was added. After stirring for one hour at room temperature, water was added and the reaction mixture was extracted with ether. The organic layers were washed with saturated ammonium chloride, brine, dried (magnesium sulfate) and concentrated in vacuo. Flash chromatography (silica gel, 1:9 ethyl acetate:petroleum ether) and subsequent recrystallization (methanol) gave 0.23 g of the title compound as pale green crystals: melting point 67-68 C.

14
[ 3846-73-9 ]
[ 20458-89-3 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4329 - 4331

15
[ 3846-73-9 ]
[ 3674-13-3 ]
8-methyl-2<i>H</i>-4-oxa-9b-aza-cyclopenta[<i>cd</i>]phenalene-1,2a-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Synthesis,2002,p. 1879 - 1884

16
[ 3846-73-9 ]
[ 120-21-8 ]
4-(p-diethylamino-2'-styryl)-8-hydroxyquinoline [ No CAS ]
4-(p-diethylamino-2'-styryl)-8-hydroxyquinoline [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2004,vol. 51,p. 735 - 742

17
[ 3846-73-9 ]
[ 14510-07-7 ]

Reference： [1]Journal of the Chinese Chemical Society,2004,vol. 51,p. 735 - 742
[2]Helvetica Chimica Acta,1956,vol. 39,p. 1676,1680
[3]Tetrahedron Letters,2016,vol. 57,p. 2797 - 2799

18
[ 3846-73-9 ]
[ 111115-16-3 ]

Reference： [1]Journal of the Chinese Chemical Society,2004,vol. 51,p. 735 - 742
[2]Helvetica Chimica Acta,1956,vol. 39,p. 1676,1680
[3]Tetrahedron Letters,2016,vol. 57,p. 2797 - 2799

19
[ 3846-73-9 ]
4-(p-methoxy-2'-styryl)quinolin-8-ol [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2004,vol. 51,p. 735 - 742

20
[ 3846-73-9 ]
4-(2'-naphthalenevinyl)quinolin-8-ol [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2004,vol. 51,p. 735 - 742

21
[ 3846-73-9 ]
[ 249614-28-6 ]

Reference： [1]Synthesis,1999,p. 1819 - 1829

22
[ 3846-73-9 ]
1,2-Di(8-hydroxyquinolin-4-yl)ethane [ No CAS ]

Reference： [1]Synthesis,1999,p. 1819 - 1829

23
[ 3846-73-9 ]
[ 249614-32-2 ]

Reference： [1]Synthesis,1999,p. 1819 - 1829

24
[ 3846-73-9 ]
2,7-dimethyl-1,10-phenanthroline [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 2937 - 2944

25
[ 61703-95-5 ]
[ 3846-73-9 ]

Yield	Reaction Conditions	Operation in experiment
		[1805] Into a 100 mL round bottom flask containing a stirring bar and fitted with a reflux condenser and a septum was placed 10 mL 70% sulfuric acid, sodium iodide (0.23 g, 0.24 mmol) and anisidine (2.96 g, 24 mmol). This mixture was heated to 110 C., and to it was added methyl vinyl ketone (3.2 mL, 38.45 mmol) slowly over 5 hours via a syringe pump. After heating an additional hour, the reaction was cooled and poured into 50 mL 1M aqueous Na2CO3 and extracted with CH2Cl2. The combined organic extracts were extracted with 12M HCl. The acidic extracts were neutralized with 6M NaOH and extracted with CH2Cl2. The combined organic extracts were washed with water, brine dried over Na2SO4, filtered and the solvent removed. The residue was dissolved in EtOAc and passed through a silica pad to get the methyl ether, which was dissolved in 50 mL HBr and heated to reflux for 30 hours, after which the reaction was cooled and neutralized with 1ON NaOH and extracted with CH2Cl2. The combined organic extracts were combined, washed with water, brine, dried over Na2SO4, filtered and the solvent removed in vacuo to give 4-methylquinolin-8-ol. [1806] 1H NMR (CDCl3) delta: 2.70(3H, s); 7.18(1H, t, j=4Hz); 7.27(1H, d, j=4.2 Hz); 7.47(1H, d, j=4Hz); 8.63(1H, d,j=4.2 Hz) ES MS M+1=160

Reference： [1]Patent: US2005/10048,2005,A1 .Location in patent: Page/Page column 41
[2]Organometallics,2010,vol. 29,p. 1465 - 1471

26
[ 3846-73-9 ]
[ 104-83-6 ]
[ 280135-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In ethanol;	8-(4-Chlorobenzyloxy)-4-methylquinoline (Step A): 4-methyl-8-hydroxy quinoline (2.65 g, 16.6 mmol) [prep. acc. P. Belser, S. Bernhard, U. Guerig, Tetrahedron 52, 1996, 2937-2944] was dissolved in a warm solution of KOH (930 mg, 16.6 mmol) in ethanol (50 mL). The mixture was heated to reflux and a solution of 4-chlorobenzyl chloride (3.5 g, 21.7 mmol) in ethanol (20 ml) was added dropwise to the refluxing solution during a period of 30 min. Refluxing was continued for 16 h. The solution was filtered by suction, and the filtrate was concentrated. The residue was diluted with ethyl acetate (100 ml), extracted with water (100 mL), dried (MgSO4) and concentrated. Flash chromatography (silicagel, hexane:ethyl acetate, 3:1) provided 1.69 (34%) beige solid. 1H NMR (CDCl3): delta 2.69 (s, 3H), 5.41 (s, 2H), 7.00 (d, J=7.7 Hz, 1H), 7.30 (d, J=4.3 Hz, 1H), 7.33 (d, J=8.5 Hz, 2H), 7.40 (dd, J=7.7, 8.3 Hz, 1H), 7.47 (d, J=8.5 Hz, 2H), 7.58 (d, J=8.5 Hz, 1H), 8.85 (d, J=4.3 Hz, 1H); GC-MS (pos.): 283.

Reference： [1]Patent: US6613942,2003,B1

27
[ 3846-73-9 ]
[ 100-39-0 ]
4-(2-phenylethyl)-8-quinolinol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; water;	(A) 4-(2-Phenylethyl)-8-quinolinol A solution of 0.60 ml (4.2 mmol, 2.2 eq.) of diisopropylamine in 10 ml of dry tetrahydrofuran was cooled to -78 C. and 1.6 ml (3.8 mmol, 2 eq.) of 2.4M n-butyl lithium in hexane was added dropwise. The reaction was warmed to 0 C., stirred for 15 minutes and 0.30 g (1.9 mmol) of <strong>[3846-73-9]4-methyl-8-quinolinol</strong> (see Example 1A) in 10 ml of dry tetrahydrofuran was added. The temperature was maintained at 0 C. for 24 hours, then was cooled to -78 C. and 0.23 ml (1.9 mmol, 1 eq.) of benzyl bromide was added. The reaction was stirred at -78 C. for one hour then stirred at room temperature for one hour. Water was added and this was extracted with ether. The organic layers were washed with saturated ammonium chloride, brine, dried (magnesium sulfate) and concentrated in vacuo. Purification by flash chromatography (silica gel, 1:4 ethyl acetate:petroleum ether) and recrystallization (petroleum ether) gave 240 mg of the title compound as pale green crystals: melting point 102-103 C.

Reference： [1]Patent: US4843082,1989,A

28
[ 3846-73-9 ]
[ 111-25-1 ]
4-heptyl-8-quinolinol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane;	(A) 4-Heptyl-8-quinolinol To a solution of 1.10 ml (7.88 mmol) of diisopropylamine in 20 ml of tetrahydrofuran at 0 C. under argon was added 4.1 ml (6.23 mmol) of 1.52M n-butyl lithium in hexanes dropwise. To the lithium diisopropylamide solution was added 502.0 mg (3.15 mmol) of <strong>[3846-73-9]4-methyl-8-quinolinol</strong> (see example 1A) in 10 ml of tetrahydrofuran over 15 minutes at 0 C. The dark solution, which contained some insoluble material, was allowed to stir for five hours at 0 C., cooled to -78 C. and 0.46 ml (3.31 mmol) of 1-bromohexane was added. After 30 minutes at -78 C., the reaction was allowed to warm gradually from -30 C. to room temperature over 1.5 hours. The solution was allowed to stir for 45 minutes at room temperature, quenched with pH 6.5 phosphate buffer and extracted with ether. The ether extract was washed with water and brine, dried (magnesium sulfate) and evaporated to afford 757 mg of a yellow-brown solid. This material was dissolved in hot hexane, filtered to remove an insoluble residue and the filtrate was evaporated. Recrystallization from heptane provided 511.7 mg of the title compound as yellow plates: melting point 92-93.5 C.

Reference： [1]Patent: US4843082,1989,A

29
[ 3846-73-9 ]
nickel(II) nitrate [ No CAS ]
[ 56127-84-5 ]

Reference： [1]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ni: MVol.C1, 167, page 384 - 386

30
[ 3846-73-9 ]
gallium(III) nitrate hexahydrate [ No CAS ]
[ 136739-74-7 ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 6300 - 6307

31
[ 3846-73-9 ]
[ 7733-02-0 ]
[ 14406-95-2 ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1985,vol. 24,p. 158 - 160

32
ammonium acetate [ No CAS ]
[ 7446-70-0 ]
[ 3846-73-9 ]
tris(4-methyl-8-oxy-quinolinato)aluminium(III)hydrate [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1991,vol. 46,p. 901 - 911

33
[ 7446-70-0 ]
[ 3846-73-9 ]
[ 136779-65-2 ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 6300 - 6307

34
ammonium acetate [ No CAS ]
[ 3846-73-9 ]
gallium(III) nitrate nonahydrate [ No CAS ]
tris(4-methyl-8-oxy-quinolinato)gallium(III)hydrate [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1991,vol. 46,p. 901 - 911

35
[ 3846-73-9 ]
manganese(II) perchlorate [ No CAS ]
4-methyl-quinolin-8-ol; manganese (II)-salt [ No CAS ]

Reference： [1]Spectrochimica Acta,1956,vol. 8,p. 1 - 8
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Mn: MVol.D3, 16.1.25.5, page 179 - 183

36
[ 3846-73-9 ]
manganese(II) nitrate [ No CAS ]
4-methyl-quinolin-8-ol; manganese (II)-salt [ No CAS ]

Reference： [1]Spectrochimica Acta,1956,vol. 8,p. 1 - 8
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Mn: MVol.D3, 16.1.25.5, page 179 - 183

37
[ 3846-73-9 ]
hydrous trichloronitrosylruthenium(III) [ No CAS ]
cis-1-RuCl(4-MeC₉H₅N₈-O)2(NO) [ No CAS ]
cis-2-RuCl(4-MeC₉H₅N₈-O)2(NO) [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 89 - 97

38
[ 3846-73-9 ]
[ 18990-48-2 ]
[ 70212-10-1 ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1982,vol. 21,p. 718 - 719

39
[ 3846-73-9 ]
[ 7646-79-9 ]
[ 18990-48-2 ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1982,vol. 21,p. 718 - 719

40
[ 3846-73-9 ]
[ 124-38-9 ]
[ 422550-71-8 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2 8-Hydroxy-4-methylquinoline-7-carboxylic acid (2b) Into a 100 mL round bottom flask fitted with a stirring bar and a nitrogen inlet was placed 50 mL dry methanol. To this was added sodium (.163 g, 6.78 mmol) and the reaction was allowed to stir until all the metal was dissolved. 4-Methylquinolin-8-ol (0.83 g, 5.21 mmol) was added and the mixture stirred for 15 min, followed by removal of the solvent in vacuo. The resulting white solid was transferred to a high pressure reaction vessel, which was charged with CO2 to 40 bar and heated to 170 C. for 3 days. After cooling and venting the gas, the brown residue was dissolved in water, filtered and acidified with 10% HCl. The water was removed in vacuo and thoroughly dried under hivac. The residue was slurried in MeOH, filtered and the solvent removed to give <strong>[3846-73-9]8-hydroxy-4-methylquinoline</strong>-7-carboxylic acid. 1H NMR (CDCl3) delta: 3.02 (3H, s); 7.73(1H, d, j=8.9 Hz), 8.05(1H, d, j=5.1 Hz); 8.27(1 H, d, j=8.9 Hz); 9.28(1H, d, j=5.3 Hz) ES MS M+1=204

Reference： [1]Patent: US2005/10048,2005,A1 .Location in patent: Page/Page column 42

41
[ 3846-73-9 ]
[ 75-03-6 ]
[ 61704-08-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;	The intermediate INT 1 was synthesized through ring closure from 2-aminophenol reacted with methyl vinyl ketone. INT 1 was reacted with various alkyl halides to afford 8-alkoxy-4methylquinoline derivatives as intermediates. Corresponding Rr(CH2)_,OH was reacted with intermediates to synthesize series of compounds J and I. The protective group J was removed by hydrogenation (method illustrated in example 1) to obtain compound K.
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;	Example 7 - Preparation of 8-hydroxyquino -yi) or (S-alkovyquino -yl) aikyl alcohols SWT 1 11 = 11-12 n = 11-12 K1 - K2 J1 - J2 Reagents and conditions: (a) methyl vinyl ketone, HCL reflux, (b) Mel. sCCh, acetone, rt 8h; Elf or 2~bromopropane or methylenecyclopropyl bromide, K2CO3, DMF, 60 6C, (c) I) LH.MDS, THF, 0 C, 1 h.: 2) Br(CH2)..i H, rt. (d) BnBr. KOM, EtOH, reflux, (e) H Pd/C, MeOH, rt 24 h. Method: Te intermediate INT was synthesized through ring closure from 2-arninophenol reacted with methyl vin l ketone. INT I was reacled with various aJkyl halides to afford 8-alkoxy- 4methylquino.)me derivatives as intermediates. Corresponding Brt'CHs iOH was reacted with intermediates to synthesize series of compounds 3 and I. The protective group J was removed by hydrogenaiiori (method iliustraied in example I) to obtain compound K. 1 1 -(S-nietlioxyquinoIin-4-yl)imde?aii-i-oI ( I) YD: 34%. lH NMR (400 MHz, CDt) 88.80 (ckt J - 4.4, 0.6 Hz. IH), 7.59 (dd, J ~ 8.4, 0.8 Hz, I H), 7.44-7.49 (m, 1H 7.03 (d. J - 7.6 Hz, Hh 4.08 (3, 3H); 3.63 ( J ::: 6.8 Hz, 2H), 3.03 (t J - 7.6 Hz, 2H), 1.74 (quia - 7.6 Hz, 2H), S .55 (quin, J - 7.2 Hz, 2H), 1.23-1.45 (br, 1SH); MS. m/z 329.9, JM+Hf .

Reference： [1]Patent: US2014/296251,2014,A1 .Location in patent: Paragraph 0246 - 0248
[2]Patent: WO2014/163622,2014,A1 .Location in patent: Page/Page column 34

42
[ 3846-73-9 ]
11-(8-methoxyquinolin-4-yl)undecan-1-ol [ No CAS ]

Reference： [1]Patent: US2014/296251,2014,A1

43
[ 3846-73-9 ]
11-(8-ethoxyquinolin-4-yl)undecan-1-ol [ No CAS ]

Reference： [1]Patent: US2014/296251,2014,A1

44
[ 3846-73-9 ]
11-(8-(benzyloxy)quinolin-4-yl)undecan-1-ol [ No CAS ]

Reference： [1]Patent: US2014/296251,2014,A1

45
[ 3846-73-9 ]
4-(11-hydroxyundecyl)quinolin-8-ol [ No CAS ]

Reference： [1]Patent: US2014/296251,2014,A1

46
[ 3846-73-9 ]
[ 74-88-4 ]
[ 61703-95-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; at 20℃; for 8.0h;	The intermediate INT 1 was synthesized through ring closure from 2-aminophenol reacted with methyl vinyl ketone. INT 1 was reacted with various alkyl halides to afford 8-alkoxy-4methylquinoline derivatives as intermediates. Corresponding Rr(CH2)_,OH was reacted with intermediates to synthesize series of compounds J and I. The protective group J was removed by hydrogenation (method illustrated in example 1) to obtain compound K.
	With potassium carbonate; In acetone; at 20℃; for 8.0h;	Example 7 - Preparation of 8-hydroxyquino -yi) or (S-alkovyquino -yl) aikyl alcohols SWT 1 11 = 11-12 n = 11-12 K1 - K2 J1 - J2 Reagents and conditions: (a) methyl vinyl ketone, HCL reflux, (b) Mel. sCCh, acetone, rt 8h; Elf or 2~bromopropane or methylenecyclopropyl bromide, K2CO3, DMF, 60 6C, (c) I) LH.MDS, THF, 0 C, 1 h.: 2) Br(CH2)..i H, rt. (d) BnBr. KOM, EtOH, reflux, (e) H FontWeight="Bold" FontSize="10" Pd/C, MeOH, rt 24 h. Method: Te intermediate INT was synthesized through ring closure from 2-arninophenol reacted with methyl vin l ketone. INT I was reacled with various aJkyl halides to afford 8-alkoxy- 4methylquino.)me derivatives as intermediates. Corresponding Brt'CHs iOH was reacted with intermediates to synthesize series of compounds 3 and I. The protective group J was removed by hydrogenaiiori (method iliustraied in example I) to obtain compound K. 1 1 -(S-nietlioxyquinoIin-4-yl)imde?aii-i-oI ( I) YD: 34%. lH NMR (400 MHz, CDt) 88.80 (ckt J - 4.4, 0.6 Hz. IH), 7.59 (dd, J ~ 8.4, 0.8 Hz, I H), 7.44-7.49 (m, 1H 7.03 (d. J - 7.6 Hz, Hh 4.08 (3, 3H); 3.63 ( J ::: 6.8 Hz, 2H), 3.03 (t J - 7.6 Hz, 2H), 1.74 (quia - 7.6 Hz, 2H), S .55 (quin, J - 7.2 Hz, 2H), 1.23-1.45 (br, 1SH); MS. m/z 329.9, JM+Hf .

Reference： [1]Organic Letters,2018,vol. 20,p. 1195 - 1199
[2]Patent: US2014/296251,2014,A1 .Location in patent: Paragraph 0246 - 0248
[3]Patent: WO2014/163622,2014,A1 .Location in patent: Page/Page column 34
[4]Patent: TWI543969,2016,B .Location in patent: Page/Page column 52

47
[ 3846-73-9 ]
[ 75-26-3 ]
C₁₃H₁₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;	General procedure: Example 7 - Preparation of 8-hydroxyquino -yi) or (S-alkovyquino -yl) aikyl alcohols SWT 1 11 = 11-12 n = 11-12 K1 - K2 J1 - J2 Reagents and conditions: (a) methyl vinyl ketone, HCL reflux, (b) Mel. sCCh, acetone, rt 8h; Elf or 2~bromopropane or methylenecyclopropyl bromide, K2CO3, DMF, 60 6C, (c) I) LH.MDS, THF, 0 C, 1 h.: 2) Br(CH2)..i H, rt. (d) BnBr. KOM, EtOH, reflux, (e) H Pd/C, MeOH, rt 24 h. Method: Te intermediate INT was synthesized through ring closure from 2-arninophenol reacted with methyl vin l ketone. INT I was reacled with various aJkyl halides to afford 8-alkoxy- 4methylquino.)me derivatives as intermediates. Corresponding Brt'CHs iOH was reacted with intermediates to synthesize series of compounds 3 and I. The protective group J was removed by hydrogenaiiori (method iliustraied in example I) to obtain compound K. 1 1 -(S-nietlioxyquinoIin-4-yl)imde?aii-i-oI ( I) YD: 34%. lH NMR (400 MHz, CDt) 88.80 (ckt J - 4.4, 0.6 Hz. IH), 7.59 (dd, J ~ 8.4, 0.8 Hz, I H), 7.44-7.49 (m, 1H 7.03 (d. J - 7.6 Hz, Hh 4.08 (3, 3H); 3.63 ( J ::: 6.8 Hz, 2H), 3.03 (t J - 7.6 Hz, 2H), 1.74 (quia - 7.6 Hz, 2H), S .55 (quin, J - 7.2 Hz, 2H), 1.23-1.45 (br, 1SH); MS. m/z 329.9, JM+Hf .

Reference： [1]Patent: WO2014/163622,2014,A1 .Location in patent: Page/Page column 34

48
[ 5834-16-2 ]
[ 3846-73-9 ]
[ 55-21-0 ]
N-((8-hydroxy-4-methylquinolin-7-yl)(3-methylthiophen-2-yl)methyl)benzamide [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 15458 - 15461

49
[ 3846-73-9 ]
C₂₁H₂₄N₂O₃ [ No CAS ]

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2797 - 2799

50
[ 3846-73-9 ]
tris-(E)-(4-(2-ethylhexyl cyanoacrylate)-8-hydroxyquinoline)aluminum [ No CAS ]

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2797 - 2799

51
[ 18826-95-4 ]
[ 95-55-6 ]
[ 826-81-3 ]
[ 3846-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	With iron(III) chloride hexahydrate; In tetrachloromethane; at 150℃; for 8.0h;Inert atmosphere;	General procedure: A vial charged with 0.02 mmol of FeCl3·6H2O [FeCl3, FeCl2·4H2O,Fe(C5H5)2, Fe(acac)3, Fe(OAc)2, Fe2(CO)9], 2 mmol of aniline 1, 4 mmol of carbon tetrachloride and 8 mmol of 1,3-diol under argon was sealed, placed into a pressure reactor, and heated at 150C with stirring for 8 h. After the reaction completed the mixture was dissolved in hydrochloric acid, and separated. The aqueous layer was neutralized with 10% sodium hydroxide and extracted with methylene chloride. The organic layer was filtered and evaporated. The residue was distilled in a vacuum. Analytically pure samples were isolated by semi-preparative HPLC. Physical and chemical constants and spectral characteristics corresponded to those reported in [5, 6, 8-22].

Reference： [1]Russian Journal of General Chemistry,2016,vol. 86,p. 1613 - 1618
Zh. Obshch. Khim.,2016,vol. 86,p. 1135 - 1140,6

52
[ 3846-73-9 ]
C₂₄H₂₂N₂O₄ [ No CAS ]
C₂₄H₂₂N₂O₄ [ No CAS ]
C₂₄H₂₂N₂O₄ [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1195 - 1199
[2]Organic Letters,2018,vol. 20,p. 1195 - 1199

53
[ 3846-73-9 ]
[ 103854-62-2 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1195 - 1199

54
[ 3846-73-9 ]
[ 1589471-09-9 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1195 - 1199

55
[ 3846-73-9 ]
(E)-3-(8-methoxyquinolin-4-yl)acrylaldehyde [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1195 - 1199

56
[ 3846-73-9 ]
C₂₀H₁₂Br₄N₂O₂Zn [ No CAS ]

Reference： [1]Journal of Fluorescence,2018,vol. 28,p. 1121 - 1126

57
[ 3846-73-9 ]
C₁₀H₇Br₂NO [ No CAS ]

Reference： [1]Journal of Fluorescence,2018,vol. 28,p. 1121 - 1126

58
[ 3846-73-9 ]
[ 7646-85-7 ]
[ 14406-95-2 ]

Reference： [1]Journal of Fluorescence,2018,vol. 28,p. 1121 - 1126

59
[ 3846-73-9 ]
chloro(1-phenylpyrazole)iridium(III) dimer [ No CAS ]
C₂₈H₂₂IrN₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With 2-methoxy-ethanol; potassium carbonate; at 120℃; for 20.0h;Inert atmosphere; Sealed tube;	Dimer (0.1 g, 0.10 mmol, 1.0 eq), ligand (0.2 g, 9.3 mmol, 9.3 eq), potassium carbonate (0.3 g, 2.2 mmol, 22.0 eq), and ethylene glycol monomethyl ether (2 mL) are added into a seal tube (60 mL), the seal tube is air replaced with nitrogen for 5 times, heated to 120 C., allowed to react for 20 h, cooled to room temperature, filtered, and then rinsed with 30 ml EA, and finally the organic phase is purified through chromatography with the eluent of DCM:MeOH=30:1 (volume ratio) to obtain 50 mg yellow solid with a yield of 58%. A luminous spectrum of the obtained complex in DCM at room temperature is shown in FIG. 7, in which a main emission peak is at 537 nm. Thus, the obtained complex is a yellow light material. 1H-NMR (300 MHz, DMSO) delta: 8.78 (dd, J=5.1, 2.9 Hz, 2H), 8.29 (d, J=5.5 Hz, 1H), 7.58 (dd, J=8.7, 3.9 Hz, 3H), 7.45 (dd, J=6.0, 4.0 Hz, 2H), 7.00-6.82 (m, 3H), 6.78-6.54 (m, 5H), 6.27 (d, J=7.5 Hz, 1H), 6.18 (d, J=7.3 Hz, 1H), 2.64 (s, 3H). ESI MS: 639.1, [M+H]+.

Reference： [1]Patent: US2019/92798,2019,A1 .Location in patent: Paragraph 0115-019

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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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. 3846-73-9 ] {[proInfo.proName]}

Quality Control of [ 3846-73-9 ]

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[ 3846-73-9 ] Synthesis Path-Upstream 1~6

[ 3846-73-9 ] Synthesis Path-Downstream 1~59

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