[ CAS No. 2246-44-8 ] {[proInfo.proName]}

Name: 2246-44-8|2-Methylnaphthalen-1-amine|95%
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Quality Control of [ 2246-44-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 2246-44-8 ]

CAS No. :	2246-44-8	MDL No. :	MFCD00059135
Formula :	C₁₁H₁₁N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JMBLSGAXSMOKPN-UHFFFAOYSA-N
M.W :	157.21	Pubchem ID :	16733
Synonyms :

Calculated chemistry of [ 2246-44-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.09
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	53.32
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	2.86
Log Po/w (WLOGP) :	2.74
Log Po/w (MLOGP) :	2.83
Log Po/w (SILICOS-IT) :	2.74
Consensus Log Po/w :	2.61

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.23
Solubility :	0.0919 mg/ml ; 0.000585 mol/l
Class :	Soluble
Log S (Ali) :	-3.07
Solubility :	0.135 mg/ml ; 0.00086 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.09
Solubility :	0.0129 mg/ml ; 0.0000818 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 2246-44-8 ]

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

Application In Synthesis of [ 2246-44-8 ]

* 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 [ 2246-44-8 ]
Downstream synthetic route of [ 2246-44-8 ]

[ 2246-44-8 ] Synthesis Path-Upstream 1~6

1
[ 2586-62-1 ]
[ 2246-44-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With ((+/-)-binap)Ni[P(OPh)3]2*2PhCH₃; ammonia; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 1,4-dioxane at 120℃; for 18 h; Inert atmosphere; Sealed tube	General procedure: An oven-dried vial (35x12 mm) equipped with a PTFE-sealedxscrew cap was loaded with a magnetic stirrer bar, ((+/-)-binap)Ni[P(OPh)3]2*2PhCH3 (9) (39 mg, 25 mmol, 5mol-percent), (+/-)-binap (15 mg, 25 mmol, 5 mol-percent), and the corresponding aryl halide (0.50 mmol, 1.0 equiv.). The vial was then transferred into an argon-filled glovebox, where NaOtBu (216 mg, 2.20 mmol, 4.40 equiv.) and NH3 (0.5 M in 1,4-dioxane, 3.0 mL, 1.5 mmol, 3.0 equiv.) were added. The reaction vial was capped, removed from the glovebox, and placed into a preheated oil bath at 120 C to stir for 18 h. On cooling, the reaction mixture was diluted with Et2O (15 mL), and washed with 1 M NaOH (10 mL) and H2O (210 mL). The organic layer was fused onto silica and purified via flash column chromatography (EtOAc/hexanes or EtOAc/MeOH) to give the corresponding aniline. 2-Methylnaphthalen-1-amine (19k) Following the general procedure using 1-bromo-2-methylnaphthalene (84 mL mg, 0.50 mmol), the desired compound 19k was obtained after purification via flash column chromatography(hexanes/EtOAc 90 : 10) as a dark orange oil (73 mg, 0.46 mmol, 93 percent). The spectral data were in accordance with those reported in the literature.[64] Rf 0.20 (hexanes/EtOAc 90 : 10). δH (CDCl3, 500 MHz) 7.85–7.80 (2H, m, 2Ar–H),7.50–7.43 (2H, m, 2Ar–H), 7.33 (1H, d, J 8.3, Ar–H), 7.28 (1H, d, J 8.3, Ar–H), 4.11 (2H, br s, NH2), 2.38 (3H, s, CH3). δC (CDCl3, 125 MHz) 139.0 (Ar–C), 133.2 (Ar–C), 129.4 (Ar–CH), 128.6 (Ar–CH), 124.92 (Ar–CH), 124.87 (Ar–CH), 123.4 (Ar–C), 120.3 (Ar–CH), 118.3 (Ar–CH), 116.3 (Ar–CH), 17.8 (CH3).

Reference： [1] Australian Journal of Chemistry, 2015, vol. 68, # 12, p. 1842 - 1853
[2] Journal of Organic Chemistry, 2010, vol. 75, # 14, p. 4887 - 4890

2
[ 881-03-8 ]
[ 2246-44-8 ]

Reference： [1] Journal of the American Chemical Society, 1942, vol. 64, p. 2657,2660
[2] Journal of the American Chemical Society, 1942, vol. 64, p. 1475,1476
[3] Journal of the American Chemical Society, 1942, vol. 64, p. 2657,2660
[4] Journal of the American Chemical Society, 1942, vol. 64, p. 1475,1476
[5] Helvetica Chimica Acta, 1937, vol. 20, p. 1024,1028,1029,1030
[6] Chemische Berichte, 1921, vol. 54, p. 2917
[7] Justus Liebigs Annalen der Chemie, 1913, vol. 402, p. 28
[8] Bulletin de la Societe Chimique de France, 1972, p. 1551 - 1561
[9] Journal of Organic Chemistry, 1991, vol. 56, # 5, p. 1739 - 1747
[10] Chemistry - A European Journal, 2002, vol. 8, # 3, p. 632 - 640
[11] Patent: US2003/18147, 2003, A1,
[12] Patent: EP1260515, 2002, A1,
[13] Tetrahedron, 2012, vol. 68, # 46, p. 9371 - 9375,5
[14] Tetrahedron,

3
[ 34774-85-1 ]
[ 2246-44-8 ]

Reference： [1] Journal of Organic Chemistry, 1977, vol. 42, p. 3240 - 3243

4
[ 91-57-6 ]
[ 2246-44-8 ]

Reference： [1] Journal of Organic Chemistry, 1987, vol. 52, # 5, p. 753 - 759

5
[ 2246-44-8 ]
[ 2586-62-1 ]

Reference： [1] Journal of Organic Chemistry, 1977, vol. 42, p. 2426 - 2431

6
[ 2246-44-8 ]
[ 54357-18-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1964, vol. 7, p. 466 - 468
[2] Journal of the Chemical Society, 1958, p. 1426
[3] Tetrahedron,

[ 2246-44-8 ] Synthesis Path-Downstream 1~88

1
[ 64-67-5 ]
[ 2246-44-8 ]
[ 60632-35-1 ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 1475,1476

2
[ 14368-49-1 ]
[ 2246-44-8 ]
2-methyl-4-(4-nitro-phenylazo)-[1]naphthylamine [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1943,vol. 62,p. 75,84

3
[ 14289-29-3 ]
[ 2246-44-8 ]
4-(4-amino-3-methyl-[1]naphthylazo)-benzenesulfonic acid amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 811

4
[ 2154-66-7 ]
[ 2246-44-8 ]
4-(4-amino-3-methyl-[1]naphthylazo)-benzenesulfonic acid [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1913,vol. 402,p. 28

5
[ 881-03-8 ]
[ 2246-44-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium on activated charcoal; In methanol;	a) Synthesis of 1-amino-2-methylnaphthalene 10 g (53.42 mmol) of 2-methyl-1-nitronaphthalene dissolved in 125 ml of methanol and 0.57 g (0.057 g of Pd, 0.54 mmol) of palladium on activated charcoal were introduced successively into an autoclave. The suspension was heated to 50 C. during 4 hours under a pressure of 10*105 Pa of hydrogen, then filtered at ambient temperature. The solution obtained was evaporated and distilled in vacuo. This gave 6.7 g of 1-amino-2-methylnaphthalene in the form of a yellow oil with a boiling point of between 145 and 150 C. at 133.3 Pa. 1H NMR (CDCl3-300K-500 MHz) delta=2.40 (s, 3H, -CH3), 4.15 (s, broad, 2H, -NH2), 7.33 (d, 2H, H3 naphth, 3JH3-H4~- 8 Hz), 7.28 (d, 2H, H2 naphth), 7.47 (m 2H, H6-7 naphth), 7.82 (m, 2H, H8-5 naphth) in ppm.
	With hydrogen;palladium on activated charcoal; In methanol;	a) Synthesis of 1-amino-2-methylnaphthalene 10 g (53.42 mmol) of 2-methyl-1-nitronaphthalene dissolved in 125 ml of methanol and 0.57 g (0.057 g of Pd, 0.54 mmol) of palladium on activated charcoal were introduced successively into an autoclave. The suspension was heated to 50C during 4 hours under a pressure of 10 * 105Pa of hydrogen, then filtered at ambient temperature. The solution obtained was evaporated and distilled in vacuo. This gave 6.7 g of 1-amino-2-methylnaphthalene in the form of a yellow oil with a boiling point of between 145 and 150C at 133.3 Pa. 1H NMR (CDCl3- 300K - 500 MHz) delta = 2.40 (s, 3H, -CH 3), 4.15 (s, broad, 2H, -NH 2), 7.33 (d, 2H, H3 naphth,3JH3-H4~ 8 Hz), 7.28 (d, 2H, H2 naphth), 7.47 (m 2H, H6-7 naphth), 7.82 (m, 2H, H8-5 naphth) in ppm.
	With hydrazine hydrate; 10% Pd/C; In ethanol; at 65℃; for 3h;Inert atmosphere;	2-Methyl-1-nitronaphthalene (15.53 g, 82.96 mmol) in ethanol (100 mL) was heated to 65 C under argon, ferrihydrite catalyst (2.5 g) (or 10% Pd/C, 2 g), hydrazine hydrate (10 mL, 10.32 g, 205.6 mmol) were added and this mixture was stirred for 3 h at 65 C. Filtration over Celite, rotoevaporation, and vacuum drying gave the raw amine as brown oil, which was then dissolved in dichloromethane (20 mL). After dropwise addition of acetic anhydride (10 mL, 10.8 g, 105.8 mmol) in dichloromethane (15 mL), the mixture was stirred 1 h at room temperature and rotoevaporated. Recrystallization of the residue in ethanol gave the acetamide in 91% yield (86% when catalyzed by Pd/C) as white crystals. 1H (300 MHz, DMSO-d6): 9.70 (s, 1H), 7.89 (d, J=6.6 Hz, 1H), 7.86 (d, J=7.8 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.53-7.45 (m, 2H), 7.41 (d, J=8.5 Hz, 1H), 2.30 (s, 3H), 2.17 (s, 3H); 13C (75 MHz, CDCl3): delta 164.6, 149.9, 128.7, 128.1, 127.6, 126.6, 125.2, 122.2, 23.2, 18.6; MS (CI, CH4): m/z calcd for C13H13NO: 199.2; found 200.1 [MH+]. Anal. Calcd for C13H13NO: C, 78.36; H, 6.58; N, 7.03. Found: C, 78.34; H, 6.62; N, 7.01.

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 2657,2660
[2]Journal of the American Chemical Society,1942,vol. 64,p. 2657,2660
[3]Helvetica Chimica Acta,1937,vol. 20,p. 1024,1028,1029,1030
[4]Chemische Berichte,1921,vol. 54,p. 2917
[5]Justus Liebigs Annalen der Chemie,1913,vol. 402,p. 28
[6]Bulletin de la Societe Chimique de France,1972,p. 1551 - 1561
[7]Journal of Organic Chemistry,1991,vol. 56,p. 1739 - 1747
[8]Chemistry - A European Journal,2002,vol. 8,p. 632 - 640
[9]Patent: US2003/18147,2003,A1
[10]Patent: EP1260515,2002,A1
[11]Tetrahedron,2012,vol. 68,p. 9371 - 9375,5

6
[ 2246-44-8 ]
[ 1147550-11-5 ]
(2-methyl-[1]naphthyl)-thiourea [ No CAS ]

Reference： [1]Academia Republicii Populare Romine, Baza de Cercetari Stiintifice, Timisoara, Studii si Cercetari, Stiinte Chimice,1957,vol. 5,p. 611,613
Chem.Abstr.,1960,p. 19609

7
[ 2246-44-8 ]
[ 37101-23-8 ]

Reference： [1]Australian Journal of Chemistry,1972,vol. 25,p. 1355 - 1358

8
[ 2246-44-8 ]
[ 37101-21-6 ]

Reference： [1]Australian Journal of Chemistry,1972,vol. 25,p. 1355 - 1358

9
[ 2246-44-8 ]
[ 5859-45-0 ]

Reference： [1]Journal of Organic Chemistry,1977,vol. 42,p. 2426 - 2431

10
[ 2246-44-8 ]
[ 13577-15-6 ]

Reference： [1]Journal of Organic Chemistry,1977,vol. 42,p. 2426 - 2431

11
[ 2246-44-8 ]
[ 62415-75-2 ]

Reference： [1]Journal of Organic Chemistry,1977,vol. 42,p. 2426 - 2431

12
[ 2246-44-8 ]
[ 2586-62-1 ]

Reference： [1]Journal of Organic Chemistry,1977,vol. 42,p. 2426 - 2431

13
[ 2246-44-8 ]
[ 54357-18-5 ]

Reference： [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 466 - 468
[2]Journal of the Chemical Society,1958,p. 1426
[3]Tetrahedron,

14
[ 75-30-9 ]
[ 2246-44-8 ]
[ 130523-26-1 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1739 - 1747

15
[ 4541-32-6 ]
[ 2246-44-8 ]
1-<(2,2-dimethylcyclopentylidene)amino>-2-methylnaphthalene [ No CAS ]

Reference： [1]Chemische Berichte,1993,vol. 126,p. 747 - 754

16
[ 23786-93-8 ]
[ 2246-44-8 ]
1-<(cyclopentylidene)amino>-2-methylnaphthalene [ No CAS ]

Reference： [1]Chemische Berichte,1993,vol. 126,p. 747 - 754

17
[ 2246-44-8 ]
[ 53487-52-8 ]
[ 132588-74-0 ]

Reference： [1]Helvetica Chimica Acta,1990,vol. 73,p. 1515 - 1573

18
[ 2246-44-8 ]
[ 75586-72-0 ]
[ 80961-81-5 ]

Reference： [1]Journal of general chemistry of the USSR,1981,vol. 51,p. 2173 - 2176
Zhurnal Obshchei Khimii,1981,vol. 51,p. 2521 - 2525

19
[ 2246-44-8 ]
[ 65440-45-1 ]
4-(2-methyl-1-naphthylazo)-1-naphthylhydrazone of 2-naphthoic aldehyde [ No CAS ]
[ 80961-76-8 ]

Reference： [1]Journal of general chemistry of the USSR,1981,vol. 51,p. 2173 - 2176
Zhurnal Obshchei Khimii,1981,vol. 51,p. 2521 - 2525
[2]Journal of general chemistry of the USSR,1981,vol. 51,p. 2173 - 2176
Zhurnal Obshchei Khimii,1981,vol. 51,p. 2521 - 2525

20
[ 2246-44-8 ]
[ 98154-51-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 2733 - 2740

21
[ 2246-44-8 ]
[ 75-03-6 ]
[ 60632-35-1 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1739 - 1747

22
[ 591-87-7 ]
[ 2246-44-8 ]
N-allyl-1-(2-methylnaphthyl)amine [ No CAS ]
N,N-diallyl-1-(2-methylnaphthyl)amin [ No CAS ]

Reference： [1]Applied Organometallic Chemistry,2012,vol. 26,p. 550 - 555
[2]Tetrahedron,2008,vol. 64,p. 9625 - 9629
[3]Tetrahedron,2006,vol. 62,p. 3752 - 3760
[4]Tetrahedron,2006,vol. 62,p. 3752 - 3760

23
[ 25835-31-8 ]
[ 2246-44-8 ]
[ 910116-11-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4444 - 4449

24
[ 723309-02-2 ]
[ 2246-44-8 ]
[ 58859-46-4 ]
[ 2719-27-9 ]
[ 723308-10-9 ]

Yield	Reaction Conditions	Operation in experiment
		4-[5-(Cyclohexanecarbonyl-amino)-6-methyl-naphthalene-1-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester (H-22) Compound 5-(cyclohexanecarbonyl-amino)-6-methyl-naphthalene-1-sulfonyl chloride was prepared following general procedure in scheme 10, substituting 2-methyl-naphthalen-1-ylamine for 5,6,7,8-tetrahydro-naphthalen-1-ylarnine, and cyclohexanecarbonyl chloride for 2-methyl-benzoyl chloride. The title compound was made following the general procedure in Scheme 16, substituting 5-(cyclohexanecarbonyl-amino)-6-methyl-naphthalene-1-sulfonyl chloride for 5-Benzoylamio-naphthalene-1-sulfonyl chloride (44), and 4-amino-piperidine-1-carboxylic acid ethyl ester for p-anisidine. 1H NMR (300 MHz, MeOD) delta 8.59 (d, 1H), 8.19 (m, 2H), 7.61 (m, 2H), 4.02 (q, 2H), 3.81 (m, 2H), 3.21 (m, 1H), 2.78 (m, 2H), 2.62 (m, 1H), 2.40 (s, 3H), 2.09 (m, 2H), 1.92 (m, 2H), 1.50 (m, 10H), 1.21 (t, 3H); LC/MS (M+H)+ m/z 502.

Reference： [1]Patent: US2005/85518,2005,A1

25
[ 723309-02-2 ]
[ 2246-44-8 ]
[ 58859-46-4 ]
[ 2719-27-9 ]
4-[5-(Cyclohexanecarbonyl-amnino)-6-methyl-naphthalene-2-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester [ No CAS ]
[ 723309-03-3 ]

Yield	Reaction Conditions	Operation in experiment
		4-[5-(Cyclohexanecarbonyl-amnino)-6-methyl-naphthalene-2-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester (H-23) Compound 5-(Cyclohexanecarbonyl-amino)-6-methyl-naphthalene-2-sulfonyl chloride was prepared following general procedure in scheme 10, substituting 2-methyl-naphthalen-1-ylamine for 5,6,7,8-tetrahydro-naphthalen-1-ylamine, and cyclohexanecarbonyl chloride for 2-methyl-benzoyl chloride. The title compound was made following the general procedure in Scheme 16, substituting 5-(cyclohexanecarbonyl-amino)-6-methyl-naphthalene-1-sulfonyl chloride for 5-Benzoylamio-naphthalene-1-sulfonyl chloride (44), and 4-amino-piperidine-1-carboxylic acid ethyl ester for p-anisidine. 1H NMR (300 MHz, MeOD) delta 8.41 (s, 1H), 7.90 (m, 3H), 7.59 (m, 1H), 4.04 (q, 2H), 3.88 (m, 2H), 3.25 (m, 1H), 2.83 (m, 2H), 2.65 (m, 1H), 2.40 (s, 3H), 2.11 (m, 2H), 1.94 (m, 2H), 1.50 (m, 10H), 1.21 (t, 3H); LC/MS (M+H)+ m/z 502.

Reference： [1]Patent: US2005/85518,2005,A1

26
[ 2246-44-8 ]
[ 82-86-0 ]
1-(2-methyl-1-naphthylimino)-2-acenaphthenenone [ No CAS ]
bis[N,N′-(2-methyl-1-naphthyl)imino]acenaphthene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	toluene-4-sulfonic acid; In benzene;Dean-Stark trap; Heating / reflux;	L3, e.g., 1-(2-methyl-1-naphthylimino)-2-acenaphthenenone, illustrated below, was synthesized by adding 2-Methylnaphthylamine (0.43 g, 2.74 mmol) to a stirred slurry of 1,2-acenaphthenedione (0.50 g, 2.74 mmol) in benzene (90 mL). A catalytic amount of p-toluenesulfonic acid was added to the resulting slurry and the reaction mixture was then refluxed. The water formed was separated via a Dean-Stark trap. The reaction was refluxed for 2 hours and then left to stand overnight under argon. The reaction mixture was obtained as a deep green/brown solution which contained about 20% of the bisimine and 80% of the desired monoimine by G.C. analysis.

Reference： [1]Patent: US7301040,2007,B2 .Location in patent: Page/Page column 11; 21-22

27
[ 2246-44-8 ]
N-(2-bromo-phenyl)-2-[5-methyl-4-(2-methyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4444 - 4449

28
[ 2246-44-8 ]
N-(2-chloro-4-methyl-phenyl)-2-[5-methyl-4-(2-methyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4444 - 4449

29
[ 2246-44-8 ]
[ 33555-17-8 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 4511 - 4515

30
[ 2246-44-8 ]
2-methyl-1-<(2,2,5,5-tetramethylcyclopentylidene)amino>naphthalene [ No CAS ]

Reference： [1]Chemische Berichte,1993,vol. 126,p. 747 - 754

31
[ 2246-44-8 ]
1-<<2,2-bis(trideuteriomethyl)-5,5-dimethylcyclopentylidene>amino>-2-methylnaphthalene [ No CAS ]

Reference： [1]Chemische Berichte,1993,vol. 126,p. 747 - 754

32
[ 2246-44-8 ]
[ 105200-97-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 2733 - 2740

33
[ 2246-44-8 ]
[ 98154-39-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 2733 - 2740

34
[ 2246-44-8 ]
[ 105200-99-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 2733 - 2740

35
[ 2246-44-8 ]
[ 98154-41-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 2733 - 2740

36
[ 2246-44-8 ]
[ 130523-07-8 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1739 - 1747

37
[ 2246-44-8 ]
[ 130523-08-9 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1739 - 1747

38
[ 2246-44-8 ]
[ 21614-05-1 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1739 - 1747

39
[ 2246-44-8 ]
[ 130523-09-0 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1739 - 1747

40
[ 2246-44-8 ]
[ 130523-24-9 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1739 - 1747

41
[ 2246-44-8 ]
[ 132589-16-3 ]

Reference： [1]Helvetica Chimica Acta,1990,vol. 73,p. 1515 - 1573

42
[ 2246-44-8 ]
[ 132589-17-4 ]

Reference： [1]Helvetica Chimica Acta,1990,vol. 73,p. 1515 - 1573

43
[ 2246-44-8 ]
N-[4-(4-acetyl-phenylazo)-2-methyl-[1]naphthyl]-succinamic acid [ No CAS ]

Reference： [1]Svensk Kemisk Tidskrift,1944,vol. 56,p. 267,274

44
[ 2246-44-8 ]
[ 83-68-1 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1943,vol. 62,p. 75,84

45
[ 2246-44-8 ]
8-methyl-1H-benz[cd]indol-2-one [ No CAS ]

Reference： [1]Zhurnal Obshchei Khimii,1953,vol. 23,p. 798; engl. Ausg. S. 835

46
[ 2246-44-8 ]
[ 5774-05-0 ]

Reference： [1]Journal of the Chemical Society,1958,p. 1426

47
[ 2246-44-8 ]
(2-methyl-[1]naphthyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Zhurnal Obshchei Khimii,1953,vol. 23,p. 798; engl. Ausg. S. 835

48
[ 2246-44-8 ]
[ 793724-78-4 ]

Reference： [1]Journal of the Chemical Society,1939,p. 944,948

49
[ 2246-44-8 ]
N-(4-amino-2-methyl-[1]naphthyl)-benzenesulfonamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 4925,4928

50
[ 2246-44-8 ]
[ 500361-53-5 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 4925,4928

51
[ 2246-44-8 ]
N,N'-(3,3'-dimethyl-[1,1']binaphthyl-4,4'-diyl)-bis-toluene-4-sulfonamide [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1946,vol. 29,p. 1661,1663,1664

52
[ 2246-44-8 ]
diethyl-(6-methyl-5-o-tolylimino-5H-benzo[a]phenoxazin-9-yl)-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1989,1992

53
[ 2246-44-8 ]
(+/-)-N-methyl-N-(2-methyl-[1]naphthyl)-succinamic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 1475,1476

54
[ 2246-44-8 ]
N-(2-methyl-5,6,7,8-tetrahydro-[1]naphthyl)-acetamide [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1931,vol. 3,p. 448,451

55
[ 2246-44-8 ]
N-ethyl-N-(2-methyl-[1]naphthyl)-succinamic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 1475,1476

56
[ 2246-44-8 ]
(+)-N-methyl-N-(2-methyl-[1]naphthyl)-succinamic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 1475,1476

57
[ 2246-44-8 ]
(-)-N-methyl-N-(2-methyl-[1]naphthyl)-succinamic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 1475,1476

58
[ 2246-44-8 ]
4-(4-acetylamino-3-methyl-[1]naphthylazo)-benzenesulfonic acid-[2]pyridylamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 811

59
[ 2246-44-8 ]
[ 101587-64-8 ]

Reference： [1]Patent: US2816894,1953,

60
[ 2246-44-8 ]
[ 101785-04-0 ]

Reference： [1]Patent: US2816894,1953,

61
[ 2246-44-8 ]
[ 100957-38-8 ]

Reference： [1]Patent: DE963427,1952,

62
[ 2246-44-8 ]
[ 117877-97-1 ]

Reference： [1]Patent: US2816894,1953,

63
[ 2246-44-8 ]
4-(4-acetylamino-3-methyl-[1]naphthylazo)-benzenesulfonic acid acetylamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 811

64
[ 2246-44-8 ]
[ 64345-70-6 ]

Reference： [1]Journal of Organic Chemistry,1978,vol. 43,p. 524 - 525

65
[ 2246-44-8 ]
[ 37113-05-6 ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 569 - 570

66
[ 2246-44-8 ]
m-Tolyl-<3-methyl-naphthyl-(1)>-keton [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 466 - 468

67
[ 2246-44-8 ]
o-Tolyl-<3-methyl-naphthyl-(1)>-keton [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 466 - 468

68
[ 2246-44-8 ]
(4-Fluoro-3-methyl-1-naphthoyl)-m-tolyl-keton [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 569 - 570

69
[ 2246-44-8 ]
[ 95814-11-2 ]

Reference： [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 466 - 468

70
[ 2246-44-8 ]
[ 94465-22-2 ]

Reference： [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 466 - 468

71
[ 2246-44-8 ]
[ 96057-80-6 ]

Reference： [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 466 - 468

72
[ 2246-44-8 ]
[ 35187-92-9 ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 569 - 570

73
[ 2246-44-8 ]
[ 37113-10-3 ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 569 - 570

74
[ 2246-44-8 ]
[ 37113-07-8 ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 569 - 570

75
[ 2246-44-8 ]
[ 2900-27-8 ]
[ 672960-98-4 ]

Yield	Reaction Conditions	Operation in experiment
43%	With 4-methyl-morpholine; isobutyl chloroformate;	TERT-BUTYL [1- (2-METHYL-1-NAPHTHYLCARBAMOYL)-1-PHENYL-METHYL]-CARBAMATE WAS] isolated as an off-white solid (165.7mg, 43%) from BOC-phenyl glycine (250. Omg, 0. 99mmol), N-methylmorpholine (0.12mL, 1. 09mmol), [ISOBUTYLCHLOROFORMATE] (0.14mL, 1. [09MMOL), 2-METHYL-1-NAPHTHYLAMINE] [(187.] 7mg, 1. 19mmol) and N-methylmorpholine (0. [13ML,] 1. 19mmol).

Reference： [1]Patent: WO2004/22534,2004,A1 .Location in patent: Page 98

76
[ 1129-30-2 ]
[ 2246-44-8 ]
2,6-bis(1-(2-methyl-1-naphthylimino)-ethyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; acetic acid;	b) Synthesis of 2,6-bis(1-(2-methyl-1-naphthylimino) ethyl]pyridine 1.20 g (7.35 mmol) of 2,6-diacetylpyridine dissolved in 25 ml of ethanol were introduced into a 100 ml round-bottomed flask under nitrogen, with stirring. 3.0 g (20.25 mmol) of <strong>[2246-44-8]1-amino-2-methylnaphthalene</strong> dissolved in 10 ml of ethanol were then added dropwise, followed by 0.1 ml of glacial acetic acid. The mixture was heated at reflux for 18 hours, with stirring, then cooled to ambient temperature and dried in vacuo so as to obtain crude 2,6-bis[1-(2-methyl-1-naphthylimino)-ethyl]pyridine, which was dissolved in methylene chloride and neutralized with an aqueous solution of sodium carbonate.
	With sodium carbonate; In ethanol; hexane; dichloromethane; water; acetic acid; ethyl acetate;	b) Synthesis of 2,6-bis[1-(2-methyl-1-naphthylimino) ethyl]pyridine. 1.20 g (7.35 mmol) of 2,6-diacetylpyridine dissolved in 25 ml of ethanol were introduced into a 100 ml round-bottomed flask under nitrogen, with stirring. 3.0 g (20.25 mmol) of <strong>[2246-44-8]1-amino-2-methylnaphthalene</strong> dissolved in 10 ml of ethanol were then added dropwise, followed by 0.1 ml of glacial acetic acid. The mixture was heated at reflux for 18 hours, with stirring, then cooled to ambient temperature and dried in vacuo so as to obtain crude 2,6-bis[1-(2-methyl-1-naphthylimino)-ethyl]pyridine,which was dissolved in methylene chloride and neutralized with an aqueous solution of sodium carbonate. The organic phase was separated, and 100 ml of water were added thereto. After dewatering and evaporation of the organic phase, the 2,6-bis[1-(2-methyl-1-naphthylimino)ethyl]pyridine was purified by liquid chromatography on a silica column using a 25/75 v/v AcOEt/n-hexane mixture as eluent. This gave 1.33 g of yellow microcrystalline solid. 1H NMR (CDCl3- 300K - 500 MHz) delta = 2.26 (m, 12H, -CH 3imine and -CH 3 naphthyl), 7.45 (m, 6H, H5-6-7 naphth), 7.58 (d, 2H, H8 naphth, 3JH7-H8~ 8 Hz), 7.65 (d, 2H, H3 naphth,3JH3-H4~ 8 Hz), 7.85 (d, 2H, H4 naphth) 8.06 (t, 1H, Hp py,3JHm-Hp~ 8 Hz), 8.68 (d, 2H, Hm py, 3JHm-Hp~ 8 Hz) in ppm. FTIR (KBr pressing) nu = 1640 (nuC=N) imine) in cm-1.

Reference： [1]Patent: US2003/18147,2003,A1
[2]Patent: EP1260515,2002,A1

77
bis(2-chloroethyl)amine*HCl [ No CAS ]
[ 2246-44-8 ]
[ 217487-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	In chlorobenzene;	f N-(2-Methyl-1-naphthyl)piperazine 14.7 g (82.7 mmol) of bis(2-chloroethyl)amine*HCl were added to 13.0 g (82.7 mmol) of <strong>[2246-44-8]1-amino-2-methylnaphthalene</strong> in 100 ml of chlorobenzene, and the mixture was boiled under nitrogen and at reflux for 90 h. The mixture was then evaporated and the residue was partitioned between methylene chloride and water at pH=9; the organic phase was then evaporated after having been dried. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2). 11.6 g (62%) of product were isolated.
	In chlorobenzene;	f N-(2-Methyl-1-naphthyl)piperazine 14.7 g (82.7 mmol) of bis(2-chloroethyl)amine*HCl were added to 13.0 g (82.7 mmol) of <strong>[2246-44-8]1-amino-2-methylnaphthalene</strong> in 100 ml of chlorobenzene, and the mixture was boiled under nitrogen and at reflux for 90 h. The mixture was subsequently evaporated and the residue was partitioned between methylene chloride and water at pH=9; the organic phase was then evaporated after having been dried. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated.
	In chlorobenzene;	f N-(2-Methyl-1-naphthyl)piperazine 14.7 g (82.7 mmol) of bis(2-chloroethyl)amine*HCl were added to 13.0 g (82.7 mmol) of <strong>[2246-44-8]1-amino-2-methylnaphthalene</strong> in 100 ml of chlorobenzene, and the mixture was boiled under nitrogen and at reflux for 90 h. The mixture was then evaporated and the residue was partitioned between methylene chloride and water at pH=9; the organic phase was then evaporated after having been dried. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2). 11.6 g (62%) of product were isolated.

In chlorobenzene;

f) N-(2-Methyl-1-naphthyl)piperazine 14.7 g (82.7 mM [sic]) of bis(2-chloroethyl)amine*HCl were added to 13.0 g (82.7 mM [sic]) of [2246-44-8]1-amino-2-methylnaphthalene in 100 ml of chlorobenzene and refluxed under nitrogen for 90 h. The mixture was then concentrated and partitioned between methylene chloride and water at pH=9, and the organic phase was dried and concentrated. The crude product was purified by column chromatography (silica gel, eluent/THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated.

Reference： [1]Patent: US6387912,2002,B1
[2]Patent: US6387912,2002,B1
[3]Patent: US6387912,2002,B1
[4]Patent: US6159981,2000,A

78
bis(2-chloroethyl)amine *HCl [ No CAS ]
[ 2246-44-8 ]
[ 217487-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	In chlorobenzene;	f N-(2-Methyl-1-naphthyl)piperazine 14.7 g (82.7 mM [sic]) of bis(2-chloroethyl)amine *HCl were added to 13.0 g (82.7 mM [sic]) of <strong>[2246-44-8]1-amino-2-methylnaphthalene</strong> in 100 ml of chlorobenzene and refluxed under nitrogen for 90 h. The mixture was then concentrated and partitioned between methylene chloride and water at pH=9, and the organic phase was dried and concentrated. The crude product was purified by column chromatography (silica gel, eluent/THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated.

Reference： [1]Patent: US6159962,2000,A

79
α-bromopropionmethyl ester [ No CAS ]
[ 77100-13-1 ]
[ 2246-44-8 ]
[ 41253-21-8 ]
[ 77099-25-3 ]

Yield	Reaction Conditions	Operation in experiment
	In water; ethyl acetate; butanone;	EXAMPLE 3 Production of STR14 N-(2-methylnaphthyl)-N-[1,2,4-triazolyl(1)-acetyl]-alaninemethyl ester [=compound 10]. 15.9 g of N-(2-methylnaphthyl)-N-chloroacetylalaninemethyl ester (produced by reaction of 2-methylnaphthyl-1-amine and alpha-bromopropionmethyl ester and further reaction of the intermediate with chloroacetyl chloride), 9.1 g of the sodium salt of 1,2,4-triazole and 1 g of KJ in 150 ml of absolute methyl ethyl ketone are refluxed for 17 hours. The reaction mixture is cooled to room temperature, filtered, and concentrated by evaporation. The residue is taken up in 200 ml of ethyl acetate; the solution is then washed twice with 50 ml of water each time, dried with sodium sulfate and concentrated by evaporation. The brown oil remaining is purified through silica gel 60 with acetone as the eluant. The last 4 of 6 fractions are combined and the acetone is evaporated off. The diasterioisomeric mixture of the final productproduct remains as brownish oil, nD23 =1.5920.

Reference： [1]Patent: US4916157,1990,A

80
[ 108-48-5 ]
[ 5061-21-2 ]
[ 2246-44-8 ]
[ 85789-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	With Hg; In water; acetone; Petroleum ether;	EXAMPLE 9 Preparation of 3-(N-chloroacetyl-N-2-methylnaphth-1-ylamino)-gamma-butyrolactone A 200-ml round-bottom flask equipped with a heating mantle and connected to a water aspirator vacuum system was charged with 15.0 g (0.1 mcl) <strong>[2246-44-8]1-amino-2-methylnaphthalene</strong>, 16.4 g (0.1 mol) alpha-bromo-gamma-butyrolactone and 10.7 g (0.1 mol) 2,6-dimethylpyridine. The reaction mixture was maintained at about 94-101 C. and 160 mm of Hg for about 7 hours. The reaction mixture was cooled, diluted with 100 ml acetone and filtered. The filtrate was evaporated under reduced pressure to give an oily residue which was eluted through a silica gel column with 15% acetone/85% petroleum ether to give 14.6 g of 3-(N-2-methylnaphth-1-ylamino)-gamma-butyrolactone, m.p. 92-94 C. Elemental analysis for C15 H15 NO2 showed: %C, calc. 75.0, found 74.5; %H, calc. 5.9, found 5.6; %N, calc. 5.8, found 5.6.

Reference： [1]Patent: US4728669,1988,A

81
[ 1101131-26-3 ]
[ 2246-44-8 ]
[ 1101131-27-4 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 54 - 55

82
[ 2246-44-8 ]
[ 35822-58-3 ]
C₂₂H₂₅NO₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 54 - 55
[2]Chemistry Letters,2010,vol. 39,p. 643 - 645

83
[ 2246-44-8 ]
[ 583-53-9 ]
[ 1152092-29-9 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 6676 - 6677

84
[ 1155861-37-2 ]
[ 2246-44-8 ]
[ 1155860-81-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2354 - 2359

85
[ 2246-44-8 ]
[ 6258-06-6 ]
[ 1213268-78-0 ]

Yield	Reaction Conditions	Operation in experiment
	With copper; In aq. phosphate buffer; at 80 - 120℃;pH 6 - 7;Microwave irradiation;	General procedure: Sodium 1-amino-4-ar(alkyl)amino-2-sulfoanthraquinone derivatives were synthesized according to described procedures, using a Cu0-catalyzed microwave-assisted Ullmann-coupling reaction. The following general procedure was applied: A 10 mL microwave vial was charged with bromaminic acid sodium salt (7,0.2-1 mmol) and the respective amine (1.25-3 equiv). A buffer solution of Na2HPO4 (pH 9.6, 4.5 mL) and NaH2PO4 (pH 4.2,0.5 mL) and finely powdered elemental copper (0.002-0.003 g, 5-10 mol %) were then added. The mixture was irradiated in the microwave oven at 80-120C for 5-24 min (Scheme 1). After cooling to room temperature, ca. 200 mL of water was added to the filtrate and the aqueous solution was extracted 2-3 times with dichloromethane (200 mL). If needed the organic layer was washed with water and NaOH (0.1 N) to enhance transfer of the product to water. The aqueous layer was then concentrated in vacuo to a volume of 10-20 mL, and subsequently submitted to flash column chromatography using a gradient of acetone in water (5-60%) as the eluent. Fractions containing blue product were collected. The solvent was evaporated by rotary evaporation to remove acetone and reduce the water volume. Complete removal of water was then achieved by lyophilization using a freeze dryer affording the product as a blue powder. For some compounds the last step of purification (RP-18 flash chromatography) had to be repeated two to three times to obtain pure product (P95% purity as determined by HPLC-UV (254 nm)-ESI-MS.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2076 - 2086
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4363 - 4371

86
[ 2246-44-8 ]
[ 74-88-4 ]
[ 190514-63-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 5031 - 5036

87
[ 2586-62-1 ]
[ 2246-44-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With ((+/-)-binap)Ni[P(OPh)3]2*2PhCH3; ammonia; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In 1,4-dioxane; at 120℃; for 18h;Inert atmosphere; Sealed tube;	General procedure: An oven-dried vial (35x12 mm) equipped with a PTFE-sealedxscrew cap was loaded with a magnetic stirrer bar, ((+/-)-binap)Ni[P(OPh)3]2*2PhCH3 (9) (39 mg, 25 mmol, 5mol-%), (+/-)-binap (15 mg, 25 mmol, 5 mol-%), and the corresponding aryl halide (0.50 mmol, 1.0 equiv.). The vial was then transferred into an argon-filled glovebox, where NaOtBu (216 mg, 2.20 mmol, 4.40 equiv.) and NH3 (0.5 M in 1,4-dioxane, 3.0 mL, 1.5 mmol, 3.0 equiv.) were added. The reaction vial was capped, removed from the glovebox, and placed into a preheated oil bath at 120 C to stir for 18 h. On cooling, the reaction mixture was diluted with Et2O (15 mL), and washed with 1 M NaOH (10 mL) and H2O (210 mL). The organic layer was fused onto silica and purified via flash column chromatography (EtOAc/hexanes or EtOAc/MeOH) to give the corresponding aniline. 2-Methylnaphthalen-1-amine (19k) Following the general procedure using 1-bromo-2-methylnaphthalene (84 mL mg, 0.50 mmol), the desired compound 19k was obtained after purification via flash column chromatography(hexanes/EtOAc 90 : 10) as a dark orange oil (73 mg, 0.46 mmol, 93 %). The spectral data were in accordance with those reported in the literature.[64] Rf 0.20 (hexanes/EtOAc 90 : 10). deltaH (CDCl3, 500 MHz) 7.85-7.80 (2H, m, 2Ar-H),7.50-7.43 (2H, m, 2Ar-H), 7.33 (1H, d, J 8.3, Ar-H), 7.28 (1H, d, J 8.3, Ar-H), 4.11 (2H, br s, NH2), 2.38 (3H, s, CH3). deltaC (CDCl3, 125 MHz) 139.0 (Ar-C), 133.2 (Ar-C), 129.4 (Ar-CH), 128.6 (Ar-CH), 124.92 (Ar-CH), 124.87 (Ar-CH), 123.4 (Ar-C), 120.3 (Ar-CH), 118.3 (Ar-CH), 116.3 (Ar-CH), 17.8 (CH3).

Reference： [1]Australian Journal of Chemistry,2015,vol. 68,p. 1842 - 1853
[2]Journal of Organic Chemistry,2010,vol. 75,p. 4887 - 4890
[3]Organic Letters,2019,vol. 21,p. 5694 - 5698

88
[ 2246-44-8 ]
[ 1258956-50-1 ]
[ 1258956-53-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium t-butanolate; DavePhos;bis(dibenzylideneacetone)-palladium(0); In toluene; at 100℃; for 8h;Inert atmosphere;	N-(2-Methyl-1-naphthyl)-2-(1-naphthyl)-8-quinolinamine A mixture of 8-bromo-2-(1-naphthyl)quinoline (3.25 g, 9.7 mmol), 2-methyl-1-naphthalenamine (1.76 g, 11.2 mmol), Pd(dba)2 (0.12 g, 0.2 mmol), L=(N-[2'-(dicyclohexylphosphino)[1,1'-biphenyl]-2-yl]-N,N-dimethylamine (0.15 g, 0.4 mmol), NaOtBu (1.15 g, 12 mmol) and toluene (20 mL) is stirred for 8 h under an argon atmosphere at 100 C. in oil bath. The mixture is then poured into water and extracted with benzene (3*40 mL). The combined organic phases are washed with water and brine and then concentrated. The residue is purified by column chromatography (silica gel 40, hexane/toluene 4:1). Yield 3.1 g (78%).
3.1 g (78%)	Pd(dba)2; In toluene;	N-(2-Methyl-1-naphthyl)-2-(1-naphthyl)-8-quinolinamine A mixture of 8-bromo-2-(1-naphthyl)quinoline (3.25 g, 9.7 mmol), 2-methyl-1-naphthalenamine (1.76 g, 11.2 mmol), Pd(dba)2 (0.12 g, 0.2 mmol), L=(N-[2'-(dicyclohexylphosphino)[1,1'-biphenyl]-2-yl]-N,N-dimethylamine (0.15 g, 0.4 mmol), NaOtBu (1.15 g, 12 mmol) and toluene (20 mL) is stirred for 8 h under an argon atmosphere at 100 C. in oil bath. The mixture is then poured into water and extracted with benzene (3*40 mL). The combined organic phases are washed with water and brine and then concentrated. The residue is purified by column chromatography (silica gel 40, hexane/toluene 4:1). Yield 3.1 g (78%).

Reference： [1]Patent: US8153544,2012,B2 .Location in patent: Page/Page column 14-15
[2]Patent: US7858718,2010,B1

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Ghs Precautionary Statements

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Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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P103	Read label before use
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P220	Keep/Store away from clothing/combustible materials.
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P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
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
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
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. 2246-44-8 ] {[proInfo.proName]}

Quality Control of [ 2246-44-8 ]

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[ 2246-44-8 ] Synthesis Path-Upstream 1~6

[ 2246-44-8 ] Synthesis Path-Downstream 1~88

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Aryls

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[ 2246-44-8 ]