[ CAS No. 634-43-5 ] {[proInfo.proName]}

Name: 634-43-5|N-(p-Tolyl)naphthalen-1-amine|95+%
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Quality Control of [ 634-43-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 634-43-5 ]

Product Details of [ 634-43-5 ]

CAS No. :	634-43-5	MDL No. :	MFCD00035709
Formula :	C₁₇H₁₅N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RWYRKFWBKGQTLU-UHFFFAOYSA-N
M.W :	233.31	Pubchem ID :	235835
Synonyms :

Calculated chemistry of [ 634-43-5 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.06
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	78.46
TPSA :	12.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.01
Log Po/w (XLOGP3) :	4.56
Log Po/w (WLOGP) :	4.89
Log Po/w (MLOGP) :	4.43
Log Po/w (SILICOS-IT) :	4.28
Consensus Log Po/w :	4.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.69
Solubility :	0.00482 mg/ml ; 0.0000206 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.54
Solubility :	0.00679 mg/ml ; 0.0000291 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.04
Solubility :	0.0000215 mg/ml ; 0.000000092 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.68

Safety of [ 634-43-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 634-43-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 634-43-5 ]

[ 634-43-5 ] Synthesis Path-Downstream 1~57

1
[ 111-34-2 ]
[ 634-43-5 ]
[ 63151-45-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; benzene Behandeln des Rktprod_. mit Aethanol und wss. Kaliumjodid;

Reference： [1]Piljugin; Opanasenko [Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1015,1016; engl. Ausg. S. 1097]

2
[ 6358-20-9 ]
[ 634-43-5 ]
(9-diethylamino-benzo[a]phenoxazin-5-ylidene)-p-tolyl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol Behandeln der alkoh. Loesung des Chlorids mit Ammoniak;
	With acetic acid Behandeln der alkoh. Loesung des Chlorids mit Ammoniak;

Reference： [1]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]
[2]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]

3
[ 6358-20-9 ]
[ 634-43-5 ]
9-diethylamino-5-p-toluidino-benzo[a]phenoxazinylium; chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol Behandeln der alkoh. Loesung des Chlorids mit Ammoniak;
	With acetic acid Behandeln der alkoh. Loesung des Chlorids mit Ammoniak;

4
[ 634-43-5 ]
[ 55198-74-8 ]
(4-dimethylamino-phenyl)-(4-p-toluidino-[1]naphthyl)-ketone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate Zersetzung der entstandenen Verbindung mit alkoholischem Kali;
	With trichlorophosphate Zersetzung der entstandenen Verbindung mit alkoholischem Kali;

Reference： [1]Noelting [Chemische Berichte, 1904, vol. 37, p. 1910][Chemisches Zentralblatt, 1903, vol. 74, # I, p. 87] Noelting [Bulletin de la Societe industrielle de Mulhouse, vol. 72, p. 221][Chemisches Zentralblatt, 1903, vol. 74, # I, p. 87]
[2]Current Patent Assignee: Noelting - DE79390, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 221][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 221]

5
[ 634-43-5 ]
[ 55198-74-8 ]
(4-dimethylamino-phenyl)-(4-p-toluidino-[1]naphthyl)-ketone-imine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate Einleiten von Ammoniak in die alkoh. Loesung der erhaltenen Verbindung;

Reference： [1]Noelting [Chemische Berichte, 1904, vol. 37, p. 1910][Chemisches Zentralblatt, 1903, vol. 74, # I, p. 87]

6
[ 634-43-5 ]
[ 59935-39-6 ]
(4-dimethylamino-3-nitro-phenyl)-bis-(4-p-toluidino-[1]naphthyl)-methane [ No CAS ]

Reference： [1]Noelting [Bulletin de la Societe industrielle de Mulhouse, vol. 72, p. 230][Chemische Berichte, 1904, vol. 37, p. 1912]

7
[ 634-43-5 ]
(4-dimethylamino-phenyl)-(4-p-toluidino-[1]naphthyl)-ketone [ No CAS ]
(4-dimethylamino-phenyl)-bis-(4-p-toluidino-[1]naphthyl)-methylium; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate auf dem Wasserbade;

Reference： [1]Noelting [Bulletin de la Societe industrielle de Mulhouse, vol. 72, p. 235;][Chemische Berichte, 1904, vol. 37, p. 1914,1918][Chemisches Zentralblatt, 1903, vol. 74, # I, p. 87]

8
[ 634-43-5 ]
[ 100-34-5 ]
(4-phenylazo-[1]naphthyl)-p-tolyl-amine [ No CAS ]

Reference： [1]Fischer,O.; Hepp [Justus Liebigs Annalen der Chemie, 1890, vol. 256, p. 252][Justus Liebigs Annalen der Chemie, 1891, vol. 262, p. 246]

9
[ 634-43-5 ]
[ 86011-72-5 ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; sulfur

Reference： [1]Talukdar; Shirley [Journal of the American Chemical Society, 1958, vol. 80, p. 3462,3464, 3466]

10
[ 634-43-5 ]
[ 13493-36-2 ]

Yield	Reaction Conditions	Operation in experiment
	With arsenic trichloride; 1,2-dichloro-benzene
	With arsenic trichloride In 1,2-dichloro-benzene

Reference： [1]Burton; Gibson [Journal of the Chemical Society, 1926, p. 2246]
[2]Buu-Hoi,N.P. et al. [Journal of Heterocyclic Chemistry, 1966, vol. 3, p. 374 - 376]

11
[ 634-43-5 ]
[1]naphthyl-nitroso-p-tolyl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ethanol; sodium nitrite unter Eiskuehlung;

Reference： [1]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]

12
[ 634-43-5 ]
[ 108-24-7 ]
[ 963-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; zinc(II) chloride at 230℃;

Reference： [1]Buu-Hoi; Lecocq [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1944, vol. 218, p. 792]

13
[ 634-43-5 ]
[ 108-24-7 ]
N-[1]naphthyl-N-p-tolyl-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 180℃;

Reference： [1]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]

14
[ 540-23-8 ]
[ 134-32-7 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 280℃;

Reference： [1]Girard; Vogt [Bulletin de la Societe Chimique de France, 1872, vol. <2>18, p. 68][Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1871, p. 719]

15
[ 134-32-7 ]
[ 106-49-0 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-aminobenzene sulfonic acid at 230℃;
	With iodine at 260 - 270℃;
	With ammonium iodide at 230℃;

With iodine at 260 - 270℃;

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - US1921076, 1927, A
[2]Knoevenagel [Journal fur praktische Chemie (Leipzig 1954), 1914, vol. <2>89, p. 45]
[3]Hodgson; Marsden [Journal of the Chemical Society, 1938, p. 1181][Journal of the Society of Chemical Industry, London, 1939, vol. 58, p. 154,156,290]
[4]Current Patent Assignee: Knoll & Co. - DE241853, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 180][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 180]

16
[ 90-15-3 ]
[ 106-49-0 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	With calcium chloride at 280℃;

Reference： [1]Friedlaender [Chemische Berichte, 1883, vol. 16, p. 2078]

17
[ 634-43-5 ]
[ 98-88-4 ]
N-[1]naphthyl-N-p-tolyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 130 - 140℃;

Reference： [1]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]

18
[ 634-43-5 ]
[ 123-62-6 ]
[ 63039-89-4 ]

Yield	Reaction Conditions	Operation in experiment
	With zinc(II) chloride

Reference： [1]Buu-Hoi [Journal of the Chemical Society, 1950, p. 1146,1151]

19
[ 634-43-5 ]
[ 100-10-7 ]
(4-dimethylamino-phenyl)-bis-(4-p-toluidino-[1]naphthyl)-methane [ No CAS ]

Reference： [1]Noelting [Bulletin de la Societe industrielle de Mulhouse, vol. 72, p. 228][Chemische Berichte, 1904, vol. 37, p. 1911]

20
[ 634-43-5 ]
[ 90-94-8 ]
bis-(4-dimethylamino-phenyl)-(4-p-toluidino-[1]naphthyl)-methylium; chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate

Reference： [1]Noelting [Bulletin de la Societe industrielle de Mulhouse, vol. 72, p. 233;][Chemische Berichte, 1904, vol. 37, p. 1913;][Chemisches Zentralblatt, 1903, vol. 74, # I, p. 87]

21
[ 634-43-5 ]
[ 123-63-7 ]
[ 63151-45-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; benzene Erw_. des Rktprod_. mit Aethanol und wss. Kaliumjodid;

Reference： [1]Piljugin [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 353,360; engl. Ausg. S. 347, 353]

22
[ 634-43-5 ]
[ 74-86-2 ]
[ 59520-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide at 180℃;
	With potassium hydroxide at 180℃;

Reference： [1]Reppe et al. [Justus Liebigs Annalen der Chemie, 1956, vol. 601, p. 81,104]
[2]Current Patent Assignee: I.G. FARBENINDUSTRIE AG (historic) - DE636213, 1935, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 94,273][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 94,273]

23
[ 634-43-5 ]
[ 19670-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid Behandeln der alkoh. Loesung des Chlorids mit Ammoniak;

Reference： [1]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]

24
[ 634-43-5 ]
dibutyl-(5-p-tolylimino-5H-benzo[a]phenoxazin-9-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ethanol Behandeln des Reaktionsprodukts mit wss. NH₃;

Reference： [1]Crossley et al. [Journal of the American Chemical Society, 1952, vol. 74, p. 584]

25
[ 634-43-5 ]
dipentyl-(5-p-tolylimino-5H-benzo[a]phenoxazin-9-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ethanol Behandeln des Reaktionsprodukts mit wss. NH₃;

Reference： [1]Crossley et al. [Journal of the American Chemical Society, 1952, vol. 74, p. 584]

Yield	Reaction Conditions	Operation in experiment
92%	With nickel(II) bromide trihydrate; N,N-dimethyl-cyclohexanamine; C₇₀H₇₅BN₂ In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere; Irradiation;	20 Synthesis of 4-methyldiphenylamine of the following structural formula General procedure: Aniline (69.85 mg, 0.75 mmol) and 4-bromotoluene (85.52 mg, 0.5 mmol) were added under a nitrogen atmosphere.In a 10 mL reaction flask containing 1 mL of N,N-dimethylformamide,NiBr2·3H2O (2.73 mg, 0.01 mmol) was added in that order.Compound 1a (0.096 mg, 0.0001 mmol), ethylene glycol dimethyl ether (0.90 mg, 0.01 mmol), N,N-dimethylcyclohexylamine (114.5 mg, 0.90 mmol), the reaction mixture was warmed to 50 ° C, The reaction was carried out for 12 hours under blue light irradiation at a wavelength of 465 nm. After the reaction was completed, the light was stopped and heated, and the reaction flask was cooled to room temperature, and the reaction liquid was distilled under reduced pressure to remove N,N-dimethylformamide, N,N-II. Methylcyclohexylamine; dilute the residual solution with n-hexane, filter to remove insoluble inorganic salts in the residual liquid, and filter by vacuum distillationThe liquid obtained 89.8 mg of 4-methyldiphenylamine, the yield was 98%.
	Tetralon-(1)-sulfonsaeure-(3) (p-Toluidinsalz), 195grad, 5-10 Min., Ausbeute ca. 70percent;
	Tetralon-(1)-disulfonsaeure-(3.4) (p-Toluidinsalz), 210grad, 5-10 Min., Ausbeute ca.40percent;

	p-Toluidin-hydrochlorid, Tetralon-(1)-sulfonsaeure-(3) (Na- od. K-Salz), 220grad, 10 Min, Ausbeute ca. 80percent;
	p-Toluidin-hydrochlorid, Tetralon-(1)-disulfonsaeure-(3.4) (Na- od. K-Salz), 220grad, 10 Min., Ausbeute ca. 60percent;

29
[ 634-43-5 ]
[ 99153-19-2 ]

Reference： [1]Noelting [vol. 72, p. 226][Chemische Berichte, 1904, vol. 37, p. 1909][Chemisches Zentralblatt, 1903, vol. 74, # I, p. 88]

30
[ 634-43-5 ]
[ 18821-37-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid Behandeln der alkoh. Loesung des Chlorids mit Ammoniak;

Reference： [1]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]

31
[ 7664-93-9 ]
4-(4,4'-bis-dimethylamino-benzhydrylidene)-4H-naphthalen-1-one-p-tolylimine [ No CAS ]
[ 634-43-5 ]
[ 90-94-8 ]

Reference： [1]Noelting; Saas [Chemische Berichte, 1913, vol. 46, p. 961]

32
[ 106-49-0 ]
[ 90-13-1 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium hydroxide; <i>tert</i>-butyl alcohol In water at 95℃; for 24h;
93%	With 1,1'-bis-(diphenylphosphino)ferrocene; [1,1′-bis(diphenylphosphino)ferrocene]bis(triphenylphosphite)nickel(0); sodium t-butanolate In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;

Reference： [1]Xu, Chen; Gong, Jun-Fang; Wu, Yang-Jie [Tetrahedron Letters, 2007, vol. 48, # 9, p. 1619 - 1623]
[2]Kampmann, Sven S.; Sobolev, Alexandre N.; Koutsantonis, George A.; Stewart, Scott G. [Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 1967 - 1973]

33
[ 634-43-5 ]
[ 113063-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: iodine; sulfur 2: pyridine

Reference： [1]Talukdar; Shirley [Journal of the American Chemical Society, 1958, vol. 80, p. 3462,3464, 3466]

34
[ 634-43-5 ]
[ 113063-00-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: iodine; sulfur 2: pyridine 3: H₂O₂; aqueous acetic acid

Reference： [1]Talukdar; Shirley [Journal of the American Chemical Society, 1958, vol. 80, p. 3462,3464, 3466]

35
[ 634-43-5 ]
[ 116032-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: iodine; sulfur 2: NaNH₂

Reference： [1]Talukdar; Shirley [Journal of the American Chemical Society, 1958, vol. 80, p. 3462,3464, 3466]

36
[ 634-43-5 ]
(4-nitroso-[1]naphthyl)-p-tolyl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: alcohol; concentrated hydrochloric acid; sodium nitrite / unter Eiskuehlung 2: hydrochloric acid; alcohol; diethyl ether / man zerlegt es mit Ammoniak

Reference： [1]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]

37
[ 634-43-5 ]
(4-nitro-phenyl)-(4-p-toluidino-[1]naphthylimino)-acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: alcohol; concentrated hydrochloric acid; sodium nitrite / unter Eiskuehlung 2: hydrochloric acid; alcohol; diethyl ether / man zerlegt es mit Ammoniak 3: alcohol; natrium carbonate

Reference： [1]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]

38
[ 634-43-5 ]
(4-nitroso-[1]naphthyl)-p-tolyl-amine; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: alcohol; concentrated hydrochloric acid; sodium nitrite / unter Eiskuehlung 2: alcohol; diethyl ether; hydrochloric acid

Reference： [1]Gnehm; Ruebel [Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 512,513]

39
[ 68211-49-4 ]
[ 106-49-0 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; bis(tri-ortho-tolylphosphine)palladium⁽⁰⁾; sodium t-butanolate In toluene at 25℃; for 24h; Inert atmosphere;
88%	With sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 110℃; for 0.5h;

Reference： [1]Ogata, Tokutaro; Hartwig, John F. [Journal of the American Chemical Society, 2008, vol. 130, # 42, p. 13848 - 13849]
[2]Gao, Cai-Yan; Yang, Lian-Ming [Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1624 - 1627]

40
[ 90-11-9 ]
[ 106-49-0 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1,1'-bis-(diphenylphosphino)ferrocene; [1,1′-bis(diphenylphosphino)ferrocene]bis(triphenylphosphite)nickel(0); sodium t-butanolate In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;
95%	With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; for 20h; Inert atmosphere; chemoselective reaction;
93%	With potassium hydroxide In water at 60℃; for 16h; Inert atmosphere; Sealed tube;

76%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 125℃; for 24h; Inert atmosphere;	1.1.4 N-(p-tolyl)naphthalen-1-amine . p-toluidine (10.10 g, 1.3 eq, 94.2 mmol), palladium(II) acetate (490 mg, 3.0 mol. %, 2.2 mmol), BINAP (2.03 g, 4.5 mol. %, 3.3 mmol), caesium carbonate (35.40 g, 1.5 eq, 108.7 mmol) and 1-naphthylbromide (15.00 g, 1.0 eq, 72.4 mmol) were refluxed in dioxane (210 mL) at 125° C. over 24 hours. Purification by column chromatography on silica gel (n-hexane/DCM=1:1) provided 12.7 g (76% yield, HPLC purity: 99.7%, GC purity: 100%) of secondary amine.
72%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 12h; Inert atmosphere;	22 Synthesis of Intermediate (7) N-(p-tolyl)naphthalene-1-amine Under a nitrogen atmosphere, 250mL round bottom 3-neck flask p- toluidine 3.2g, 1-bromo-naphthalene 4.1g,Tris (dibenzylideneacetone naphthyridin-acetone) dipalladium (0) 0.2g,15% tris (t- butyl) phosphine 0.5g,t- butoxy sodium 3.8g, put the toluene 100ml, and stirred 12 hours at 60°C .The reaction solution after cooling was purified by silica gel filtration,Concentrated, and then carried our dichloromethane and n- hexane mixed solvent to column chromatography to give the intermediate (7) 3.4g. (72% yield)
72%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 12h; Inert atmosphere;	8 synthesis of Intermediate (8) N-(p-tolyl)naphthalene-1-amine 250mL 3-neck round bottom flask under a nitrogen atmosphere 3.2g p- toluidine, 1- bromonaphthalene 4.1g, Tris (dibenzylideneacetone) palladium (0) 0.2g, 15% tris (t- butyl) phosphine 0.5 g, t- butoxy sodium 3.8g, put the toluene 100ml, and stirred 12 hours at 60°C . Carried out after cooling the reaction solution by silica gel filtration, column chromatography, and then was concentrated in dichloromethane and n- hexane mixed solvent to give the intermediate Photography (8) 3.4g. (72% yield)
72%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 12h; Inert atmosphere;	6 Synthesis of N-(p-tolyl)naphthalen-1-amine In a 250 mL round-bottomed three-necked flask, 3.2 g of p-toluidine, 4.1 g of 1-bromonaphthalene, 0.2 g of tris (dibenzylidineacetone) dipalladium (0), 15 g of tris (t-butyl) G, t-butoxysodium 3.8g, and toluene 100ml were placed,At 60 Stir for 12 hours. The reaction solution was cooled, filtered through silica gel, concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 3.4 g of intermediate (8). (Yield: 72%)
	With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate In toluene at 100℃;

Reference： [1]Kampmann, Sven S.; Sobolev, Alexandre N.; Koutsantonis, George A.; Stewart, Scott G. [Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 1967 - 1973]
[2]Location in patent: experimental part Dumrath, Andreas; Luebbe, Christa; Neumann, Helfried; Jackstell, Ralf; Beller, Matthias [Chemistry - A European Journal, 2011, vol. 17, # 35, p. 9599 - 9604]
[3]Ansari, Tharique N.; Taussat, Armand; Clark, Adam H.; Nachtegaal, Maarten; Plummer, Scott; Gallou, Fabrice; Handa, Sachin [ACS Catalysis, 2019, vol. 9, # 11, p. 10389 - 10397]
[4]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - JP2015/512889, 2015, A Location in patent: Paragraph 0079
[5]Current Patent Assignee: SK CHEMICALS CO LTD - KR2016/91196, 2016, A Location in patent: Paragraph 0379-0381
[6]Current Patent Assignee: SK CHEMICALS CO LTD - KR2016/29962, 2016, A Location in patent: Paragraph 0179-0181
[7]Current Patent Assignee: SK CHEMICALS CO LTD - KR2016/84918, 2016, A Location in patent: Paragraph 0187-0189
[8]Li, Gen; Liu, Yongbing; Du, Haifeng [Organic and Biomolecular Chemistry, 2015, vol. 13, # 10, p. 2875 - 2878]

41
[ 634-43-5 ]
[ 174081-58-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: N-(p-tolyl)naphthalen-1-amine With potassium carbonate In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere;
70%	With bis-[(trifluoroacetoxy)iodo]benzene In 1,2-dichloro-ethane at 20℃; for 0.5h;	Oxidative Coupling of N-Arylnaphthalenamines 1; General Procedure General procedure: PIFA (0.75 equiv.) was added to a stirred solution of the appropriatenaphthalenamine 1 (0.30 mmol, 1 equiv) in DCE (3 mL) atr.t., and the mixture was stirred for 30 min. When the reactionwas complete, sat. aq NaHCO3 was added to the mixture, andthe aqueous phase was extracted with CH2Cl2. The extractswere dried (Na2SO4) and evaporated to dryness, and the cruderesidue was purified by column chromatography (silica gel,hexane-EtOAc).

Reference： [1]Li, Xin-Le; Huang, Jin-Hua; Yang, Lian-Ming [Organic Letters, 2011, vol. 13, # 18, p. 4950 - 4953]
[2]Morimoto, Koji; Koseki, Doichi; Dohi, Toshifumi; Kita, Yasuyuki [Synlett, 2017, vol. 28, # 20, p. 2941 - 2945]

42
[ 599-86-0 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: [bis(acetoxy)iodo]benzene / 0.08 h / 25 °C / Schlenk technique; Inert atmosphere 2: bismuth(lll) trifluoromethanesulfonate / methanol / 25 °C / Schlenk technique; Inert atmosphere 3: zinc; trifluoroacetic acid / methanol / 25 °C / Schlenk technique; Inert atmosphere

Reference： [1]Zhang, Li; Wang, Weibin; Fan, Renhua [Organic Letters, 2013, vol. 15, # 8, p. 2018 - 2021]

43
[ 585526-04-1 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bismuth(lll) trifluoromethanesulfonate / methanol / 25 °C / Schlenk technique; Inert atmosphere 2: zinc; trifluoroacetic acid / methanol / 25 °C / Schlenk technique; Inert atmosphere

Reference： [1]Zhang, Li; Wang, Weibin; Fan, Renhua [Organic Letters, 2013, vol. 15, # 8, p. 2018 - 2021]

44
C₁₈H₁₇NO [ No CAS ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; zinc In methanol at 25℃; Schlenk technique; Inert atmosphere;

Reference： [1]Zhang, Li; Wang, Weibin; Fan, Renhua [Organic Letters, 2013, vol. 15, # 8, p. 2018 - 2021]

45
[ 13922-41-3 ]
[ 106-49-0 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In water at 20℃; for 5h;	Preparation of diphenylamine; typical procedure General procedure: To a stirred solution of phenylboronic acid (1.0 mmol), aniline (1.0 mmol), and K2CO3 (2.0 mmol) in deionized H2O (10 mL) at room temperature was added an aqueous suspension of FePd nanowires (3.0 mol % in 3 mL of H2O). The mixture was stirred at room temperature for 5h. After completion of the reaction (as monitored by TLC), 2 M HCl was added and the catalyst was separated by applying an external magnet. The catalyst was washed with EtOAc. The mixture was extracted with EtOAc (2 * 20 mL), dried, and concentrated. The residue was subjected to gel permeation chromatography to afford pure product.

Reference： [1]Nasrollahzadeh, Mahmoud; Azarian, Abbas; Ehsani, Ali; Zahraei, Ali [Tetrahedron Letters, 2014, vol. 55, # 17, p. 2813 - 2817]

46
[ 10075-72-6 ]
[ 106-49-0 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With SingaCycle-A₃; potassium hexamethylsilazane In 1,4-dioxane; toluene at 100℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Sugahara, Tomohiro; Murakami, Kei; Yorimitsu, Hideki; Osuka, Atsuhiro [Angewandte Chemie - International Edition, 2014, vol. 53, # 35, p. 9329 - 9333,5][Angew. Chem., 2014, vol. 126, # 35, p. 9483 - 9487,5][Angewandte Chemie, 2014, vol. 126, # 35, p. 9483 - 9487,5]

47
[ 634-43-5 ]
[ 1269472-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(pentafluorophenyl)borate; hydrogen In toluene at 60℃; for 6h; Inert atmosphere; Autoclave;

Reference： [1]Li, Gen; Liu, Yongbing; Du, Haifeng [Organic and Biomolecular Chemistry, 2015, vol. 13, # 10, p. 2875 - 2878]

48
[ 634-43-5 ]
1,6-dibromo-4,9-diisopropylpyrene [ No CAS ]
C₅₆H₄₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; for 12h; Inert atmosphere;	7 synthesis of compound 7 Under a nitrogen atmosphere, 100mL round bottom 3-neck flask was charged with intermediate (4), 0.6g, Intermediate (8), 0.7g, Tris (dibenzylideneacetone) palladium (0) 0.1g, 15% tris (t- butyl) phosphine 0.1 g, t- butoxy sodium 0.8g, put the toluene 15ml, and stirred 12 hours at 80 °C A fter cooling the reaction solution by silica gel filtration, column chromatography carried out in dichloromethane, and then concentrated and n- hexane mixed solvent to obtain the compound (7) 0.6g. (56% yield)

Reference： [1]Current Patent Assignee: SK CHEMICALS CO LTD - KR2016/29962, 2016, A Location in patent: Paragraph 0221-0223

49
[ 90-90-4 ]
[ 634-43-5 ]
(4-(naphthalen-1-yl(p-tolyl)amino)phenyl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With [2,2]bipyridinyl; [NiCl(bpy)(IPr)]; sodium t-butanolate In tetrahydrofuran at 80℃; for 48h; Glovebox; Inert atmosphere;

Reference： [1]Inatomi, Takahiro; Fukahori, Yukino; Yamada, Yuji; Ishikawa, Ryuta; Kanegawa, Shinji; Koga, Yuji; Matsubara, Kouki [Catalysis science and technology, 2019, vol. 9, # 8, p. 1784 - 1793]

50
[ 78-32-0 ]
[ 134-32-7 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; potassium carbonate at 130℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube;
98%	With N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; [Pd(π-cinnamyl)Cl]₂ at 130℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Chen, Zicong; Chen, Xiangmeng; So, Chau Ming [Journal of Organic Chemistry, 2019]
[2]Chen, Zicong; Chen, Xiangmeng; So, Chau Ming [Journal of Organic Chemistry, 2019, vol. 84, # 10, p. 6366 - 6376]

51
[ 634-43-5 ]
C₁₈H₆⁽²⁾H₆Br₂ [ No CAS ]
C₅₂H₃₄⁽²⁾H₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene for 6h; Reflux;	13 Synthesis Example 13. Synthesis of Compound 67 After starting material B-2 (5.00 g, 12.7 mmol) and starting material L-1 (7.40 g, 31.7 mmol) were dissolved in 50 ml of toluene, Na-OtBu (6.10 g, 63.4 mmol), Pd2(dba)3( 0.58 g 0.6 mmol), tBu3-P (0.51 g, 1.3 mmol, 50% Solution in Toluene) was added and stirred under heating/reflux for 6 hours.After confirming the completion of the reaction, 50 ml of water was added, the toluene layer was extracted, and then 50 ml of water was added to extract the toluene layer again.The extracted solution was treated with MgSO4to remove residual moisture and dried in a vacuum oven.Thereafter, using column chromatography (dichloromethane, heptane) method, compound 67 (2.39 g, 3.4 mmol) was obtained in a yield of 27%.

Reference： [1]Current Patent Assignee: MATERIAL SCIENCE CO LTD - KR2020/52820, 2020, A Location in patent: Paragraph 0277-0280

52
[ 5720-05-8 ]
[ 134-32-7 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With C₃₇H₃₅NiO₂P₂S₂⁽¹⁺⁾*F₆P^(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃; for 10h;

Reference： [1]Kumari, Kavita; Kumar, Saurabh; Singh, Krishna Nand; Drew, Michael G. B.; Singh, Nanhai [New Journal of Chemistry, 2020, vol. 44, # 28, p. 12143 - 12153]

53
[ 86-57-7 ]
[ 106-49-0 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With bis(acetylacetonato)palladium(II); potassium phosphate tribasic trihydrate; 2-(2,6-diethyl-4-methylphenyl)-5-(2,4,6-triisopropylphenyl)imidazo[1,5-a]pyridin-2-ium chloride In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;

Reference： [1]Chen, Kai; Chen, Wanzhi; Chen, Wei; Liu, Miaochang; Wu, Huayue [ACS Catalysis, 2019, p. 8110 - 8115]

54
[ 634-43-5 ]
C₂₁H₂₀BrClSi [ No CAS ]
C₃₈H₃₄ClNSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 10h;	4 After adding reactant A-60 (60mmol) and reactant B-60 (60mmol) in dry toluene in the reaction vessel, add Pd2(dba)3 (0.66mmol),P(t-Bu)3 (3.6mmol), t-BuONa (120mmol); the temperature was raised to 110°C, and the mixture was stirred for 10h,Use diatomaceous earth to filter while hot to remove salts and catalysts. Cool the filtrate to room temperature. Then add distilled water to the filtrate for washing. After separation, the organic phase is retained. The aqueous phase is extracted with ethyl acetate, and then dried with magnesium sulfate. After the organic layer, use a rotary evaporator to remove the solvent, place it in toluene, raise the temperature to 100°C to completely dissolve the solid organic matter, then gradually reduce the temperature until most of the solid precipitates, filter, and rinse the filter cake with petroleum ether. Put it in a 65 oven to dry for 12h,Intermediate C-60 (27.9 g, yield: 82%) was obtained.

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN112851590, 2021, A Location in patent: Paragraph 0074-0078

55
[ 106-49-0 ]
[ 86-53-3 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium hexamethylsilazane In toluene at 140℃; for 6h; Inert atmosphere; Schlenk technique;

Reference： [1]Wu, Ke; Rong, Qiang; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu; Jin, Liqun; Hu, Xinquan [Advanced Synthesis and Catalysis, 2021, vol. 363, # 20, p. 4708 - 4713]

56
C₁₇H₁₄N₂ [ No CAS ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hexamethylsilazane / toluene / 6 h / 140 °C / Inert atmosphere; Schlenk technique 2: potassium hexamethylsilazane; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride / toluene / 6 h / 140 °C / Inert atmosphere; Schlenk technique
	Multi-step reaction with 2 steps 1: potassium hexamethylsilazane; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride / toluene / 6 h / 140 °C / Inert atmosphere; Schlenk technique 2: potassium hexamethylsilazane; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride / toluene / 6 h / 140 °C / Inert atmosphere; Schlenk technique

Reference： [1]Wu, Ke; Rong, Qiang; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu; Jin, Liqun; Hu, Xinquan [Advanced Synthesis and Catalysis, 2021, vol. 363, # 20, p. 4708 - 4713]
[2]Wu, Ke; Rong, Qiang; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu; Jin, Liqun; Hu, Xinquan [Advanced Synthesis and Catalysis, 2021, vol. 363, # 20, p. 4708 - 4713]

57
[ 624-31-7 ]
[ 134-32-7 ]
[ 634-43-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	With 1,1'-bis(diphenylphosphanyl)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium tertiary butoxide In toluene at 120℃; for 18h;

Reference： [1]Cremer, Christopher; Patureau, Frederic W.; Vemuri, Pooja Y. [Organic Letters, 2022, vol. 24, # 8, p. 1626 - 1630]

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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
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Health hazards
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
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H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
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H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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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. 634-43-5 ] {[proInfo.proName]}

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[ 634-43-5 ] Synthesis Path-Downstream 1~57

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Aryls

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[ 634-43-5 ]