[ CAS No. 50548-43-1 ] {[proInfo.proName]}

Name: 50548-43-1|4-Dibenzofuranamine|95%
Brand: Ambeed
SKU: A277146
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Quality Control of [ 50548-43-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 50548-43-1 ]

SDS Specification

Alternatived Products of [ 50548-43-1 ]

Product Details of [ 50548-43-1 ]

CAS No. :	50548-43-1	MDL No. :	MFCD11110988
Formula :	C₁₂H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QKBTTXJHJNXCOQ-UHFFFAOYSA-N
M.W :	183.21	Pubchem ID :	459351
Synonyms :

Calculated chemistry of [ 50548-43-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	13
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	58.12
TPSA :	39.16 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-4.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	3.5
Log Po/w (WLOGP) :	3.18
Log Po/w (MLOGP) :	2.17
Log Po/w (SILICOS-IT) :	2.72
Consensus Log Po/w :	2.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.87
Solubility :	0.0248 mg/ml ; 0.000136 mol/l
Class :	Soluble
Log S (Ali) :	-4.01
Solubility :	0.0181 mg/ml ; 0.0000987 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.6
Solubility :	0.00457 mg/ml ; 0.0000249 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.45

Safety of [ 50548-43-1 ]

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

Application In Synthesis of [ 50548-43-1 ]

* 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 [ 50548-43-1 ]
Downstream synthetic route of [ 50548-43-1 ]

[ 50548-43-1 ] Synthesis Path-Upstream 1~13

1
[ 50548-43-1 ]
[ 50548-45-3 ]

Reference： [1] Journal of the American Chemical Society, 1939, vol. 61, p. 1365,1369

2
[ 1399050-09-9 ]
[ 50548-43-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogen In ethanol	Palladium hydroxide (20percent, 0.75 g, 1.068 mmol) was added to a Parr hydrogenation bottle, and the bottle was purged with nitrogen. Next, 4-azidodibenzo[b,d]furan (7.39 g, 35.3 mmol) and 150 mL ethanol were added, and the reaction mixture was hydrogenated on Parr hydrogenator overnight. The reaction mixture was filtered through a pad of Celite^.(R)., and the Celite^.(R). was washed with dichloromethane. The filtrate was evaporated, and the residue was purified by column chromatography eluting with 50percent dichloromethane/hexanes (5.58 g, 86percent).

Reference： [1] Patent: WO2012/121936, 2012, A2, . Location in patent: Page/Page column 71
[2] Patent: US2012/228583, 2012, A1,

3
[ 100124-06-9 ]
[ 50548-43-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 6, p. 1114 - 1116
[2] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18253 - 18256

4
[ 50548-37-3 ]
[ 50548-43-1 ]
[ 1332882-09-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogenchloride In methanol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran	N-(dibenzo[b,d]furan-4-yl)acetamide (90 g, 400 mmol) was suspended in the mixture of concentrated HCl (240 mL) and methanol (240 mL). The reaction was refluxed for 2 h and then cooled to room temperature. Saturated sodium carbonate was used to neutralize the solution. The residue was collected by filtration and redissolved in DCM. After dried over sodium sulfate, the solution was concentrated to give dibenzo[b,d]furan-4-amine (67 g, 92percent yield) as brown solid. Synthesis of 1,3-Dibromodibenzo[b,d]furan-4-amine.

Reference： [1] Patent: US2011/204333, 2011, A1,

5
[ 50548-37-3 ]
[ 50548-43-1 ]

Reference： [1] Patent: EP2423206, 2012, A1, . Location in patent: Page/Page column 54

6
[ 132-64-9 ]
[ 50548-43-1 ]

Reference： [1] Tetrahedron Letters, 1984, vol. 25, # 4, p. 429 - 432
[2] Journal of the American Chemical Society, 1945, vol. 67, p. 349
[3] Patent: EP2423206, 2012, A1,
[4] Patent: US2012/228583, 2012, A1,
[5] Patent: WO2012/121936, 2012, A2,

7
[ 19261-06-4 ]
[ 50548-43-1 ]

Reference： [1] Journal of the American Chemical Society, 1944, vol. 66, p. 1884
[2] Journal of the American Chemical Society, 1935, vol. 57, p. 1123,1125

8
[ 137959-93-4 ]
[ 50548-43-1 ]

Reference： [1] Journal of the American Chemical Society, 1945, vol. 67, p. 349

9
[ 67-62-9 ]
[ 132-64-9 ]
[ 50548-43-1 ]

Reference： [1] Iowa State College Journal of Science, 1943, vol. 18, p. 98,99
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 580,582
[3] Journal of the American Chemical Society, 1953, vol. 75, p. 4843

10
[ 873974-43-7 ]
[ 50548-43-1 ]

Reference： [1] Iowa State College Journal of Science, 1945, vol. 20, p. 15,17

11
[ 86607-81-0 ]
[ 50548-43-1 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1941, vol. 16, p. 62[2] Chem. Zentralbl., 1942, vol. 113, # I, p. 195
[3] Nippon Kagaku Kaishi, 1938, vol. 59, p. 945,950[4] Chem.Abstr., 1939, p. 603

12
[ 854395-98-5 ]
[ 50548-43-1 ]

Reference： [1] Nippon Kagaku Kaishi, 1938, vol. 59, p. 945,950[2] Chem.Abstr., 1939, p. 603

13
[ 667937-27-1 ]
[ 50548-43-1 ]

Reference： [1] Nippon Kagaku Kaishi, 1938, vol. 59, p. 945,950[2] Chem.Abstr., 1939, p. 603

[ 50548-43-1 ] Synthesis Path-Downstream 1~88

1
[ 67-62-9 ]
[ 132-64-9 ]
[ 50548-43-1 ]

Reference： [1]Iowa State College Journal of Science,1943,vol. 18,p. 98,99

2
[ 19261-06-4 ]
[ 50548-43-1 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1884
[2]Journal of the American Chemical Society,1935,vol. 57,p. 1123,1125

3
[ 50548-43-1 ]
[ 18721-64-7 ]
(2-dibenzofuran-4-ylamino-ethyl)-malonic acid diethyl ester [ No CAS ]

Reference： [1]Iowa State College Journal of Science,1943,vol. 18,p. 98,99

4
[ 50548-43-1 ]
[ 454-89-7 ]
[ 574-83-4 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 426

5
[ 50548-43-1 ]
[ 108-24-7 ]
[ 50548-37-3 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369

6
[ 50548-43-1 ]
[ 104-77-8 ]
N,N-diethyl-N'-dibenzofuran-4-yl-propanediyldiamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 580,582

7
[ 50548-43-1 ]
[ 121-60-8 ]
N-acetyl-sulfanilic acid dibenzofuran-4-ylamide [ No CAS ]

Reference： [1]Iowa State College Journal of Science,1943,vol. 18,p. 98,99

8
[ 50548-43-1 ]
[ 174187-07-6 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 3149,3151

9
[ 50548-43-1 ]
[ 6783-65-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1957,vol. <4> 4,p. 136,145
[2]Chemistry of Heterocyclic Compounds,1999,vol. 35,p. 557 - 560

10
dibenzofuran-4-carboxylic acid amide [ No CAS ]
[ 50548-43-1 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369
[2]Journal of the American Chemical Society,1944,vol. 66,p. 1884

11
[ 137959-93-4 ]
[ 50548-43-1 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 349

12
[ 873974-43-7 ]
[ 50548-43-1 ]

Reference： [1]Iowa State College Journal of Science,1945,vol. 20,p. 15,17

13
[ 86607-81-0 ]
[ 50548-43-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1941,vol. 16,p. 62
Chemisches Zentralblatt,1942,vol. 113,p. 195

14
[ 132-64-9 ]
[ 50548-43-1 ]

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 429 - 432
[2]Journal of the American Chemical Society,1945,vol. 67,p. 349
[3]Patent: EP2423206,2012,A1
[4]Patent: US2012/228583,2012,A1
[5]Patent: WO2012/121936,2012,A2

15
[ 50548-43-1 ]
2-(dibenzofuran)hydrazine hydrochloride [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 529 - 532
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 631 - 634

16
C₂₄H₁₈N₃O₄P [ No CAS ]
[ 50548-43-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 1524 - 1530

17
[ 50548-43-1 ]
[ 75-87-6 ]
[ 258327-61-6 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1999,vol. 35,p. 557 - 560

19
[ 137959-93-4 ]
ammonium hydroxide [ No CAS ]
copper (I)-bromide [ No CAS ]
[ 50548-43-1 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 349

20
[ 19261-06-4 ]
ammonium hydroxide [ No CAS ]
Na₂S₂O₅ [ No CAS ]
[ 50548-43-1 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1884

21
[ 50548-43-1 ]
[ 3282-30-2 ]
N-(dibenzofuran-4-yl)-2,2-dimethylpropionamide [ No CAS ]

Reference： [1]Australian Journal of Chemistry,2001,vol. 54,p. 177 - 180

22
[ 50548-43-1 ]
[ 32387-96-5 ]
2,3-diphenyl-quinoxaline-6-carboxylic acid dibenzofuran-4-ylamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 815 - 820

23
[ 50548-43-1 ]
N-(6-formyldibenzofuran-4-yl)-2,2-dimethylpropionamide [ No CAS ]

Reference： [1]Australian Journal of Chemistry,2001,vol. 54,p. 177 - 180

24
[ 50548-43-1 ]
[ 240-25-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1999,vol. 35,p. 557 - 560
[2]Chemistry of Heterocyclic Compounds,1999,vol. 35,p. 557 - 560

25
[ 50548-43-1 ]
3-hydroxybenzo[b]furo[3,2-g]indole [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1999,vol. 35,p. 557 - 560

26
[ 132-64-9 ]
benzofurane, thionaphthene, methylbenzothiophene, various hydrocarbons [ No CAS ]
[ 50548-43-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 1524 - 1530

27
[ 50548-43-1 ]
[ 98189-30-1 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 529 - 532
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 631 - 634

28
[ 50548-43-1 ]
[ 98189-31-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 529 - 532
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 631 - 634

29
[ 50548-43-1 ]
[ 50548-40-8 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369

30
[ 50548-43-1 ]
[ 50548-45-3 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369

31
[ 50548-43-1 ]
[ 54470-37-0 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369

32
[ 50548-43-1 ]
[ 50548-39-5 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369

33
[ 50548-43-1 ]
[ 93533-84-7 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369

34
[ 50548-43-1 ]
[ 107624-55-5 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369

35
[ 50548-43-1 ]
[ 50548-38-4 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369

36
[ 50548-43-1 ]
[ 42747-98-8 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369

37
[ 50548-43-1 ]
[ 111091-95-3 ]

Reference： [1]Iowa State College Journal of Science,1943,vol. 18,p. 98,99

38
[ 854395-98-5 ]
[ 50548-43-1 ]

Reference： [1]Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan,1938,vol. 59,p. 945,950
Chem.Abstr.,1939,p. 603

39
[ 667937-27-1 ]
[ 50548-43-1 ]

Reference： [1]Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan,1938,vol. 59,p. 945,950
Chem.Abstr.,1939,p. 603

40
2,2'-diacetoxy-3,3'-dinitro-biphenyl [ No CAS ]
[ 50548-43-1 ]

Reference： [1]Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan,1938,vol. 59,p. 945,950
Chem.Abstr.,1939,p. 603

41
[ 100124-06-9 ]
[ 50548-43-1 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 1114 - 1116
[2]Journal of the American Chemical Society,2012,vol. 134,p. 18253 - 18256

42
[ 128-08-5 ]
[ 50548-43-1 ]
[ 1332882-09-3 ]

Yield	Reaction Conditions	Operation in experiment
122%	In hexane; ethyl acetate; N,N-dimethyl-formamide;	Dibenzo[b,d]furan-4-amine (33.4 g, 182 mmol) was dissolved in DMF (300 mL) and cooled to 0 C. by ice bath. 1-bromopyrrolidine-2,5-dione (68.1 g, 383 mmol) was dissolved in DMF (300 mL) and added into the reaction solution dropwise. After the addition, the reaction was stirred at room temperature overnight. Then the reaction mixture was diluted by EtOAc and washed by 10% LiCl solution three times and saturated sodium bicarbonate twice. The organic layer was dried over sodium sulfate and concentrated. The crude product was purified with silica gel column (<15% EtOAc in hexane) to give red brown solid 1,3-dibromo<strong>[50548-43-1]dibenzo[b,d]furan-4-amine</strong> (76 g, 122% yield, containing some succinimide).

Reference： [1]Patent: US2011/204333,2011,A1

43
[ 50548-37-3 ]
[ 50548-43-1 ]
[ 1332882-09-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogenchloride; In methanol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;	N-(dibenzo[b,d]furan-4-yl)acetamide (90 g, 400 mmol) was suspended in the mixture of concentrated HCl (240 mL) and methanol (240 mL). The reaction was refluxed for 2 h and then cooled to room temperature. Saturated sodium carbonate was used to neutralize the solution. The residue was collected by filtration and redissolved in DCM. After dried over sodium sulfate, the solution was concentrated to give dibenzo[b,d]furan-4-amine (67 g, 92% yield) as brown solid. Synthesis of 1,3-Dibromodibenzo[b,d]furan-4-amine.

Reference： [1]Patent: US2011/204333,2011,A1

44
[ 50548-43-1 ]
[ 1332882-10-6 ]

Reference： [1]Patent: US2011/204333,2011,A1

45
[ 50548-43-1 ]
[ 1332882-11-7 ]

Reference： [1]Patent: US2011/204333,2011,A1

46
[ 50548-43-1 ]
[ 1332882-12-8 ]

Reference： [1]Patent: US2011/204333,2011,A1

47
[ 50548-43-1 ]
[ 1332882-13-9 ]

Reference： [1]Patent: US2011/204333,2011,A1
[2]Patent: US2011/204333,2011,A1

48
[ 50548-43-1 ]
[ 1332882-14-0 ]

Reference： [1]Patent: US2011/204333,2011,A1

49
[ 50548-43-1 ]
[ 1332882-15-1 ]
[ 1332882-14-0 ]

Reference： [1]Patent: US2011/204333,2011,A1
[2]Patent: US2011/204333,2011,A1

50
[ 50548-43-1 ]
[ 1332882-15-1 ]

Reference： [1]Patent: US2011/204333,2011,A1
[2]Patent: US2011/204333,2011,A1
[3]Patent: US2011/204333,2011,A1

51
[ 50548-37-3 ]
[ 50548-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	With water; potassium hydroxide; In ethanol; toluene; at 110℃; for 8h;	8.2g of intermediate M4, 12.2g of potassium hydroxide, 14 mL of clean water, 37 mL of toluene and 74 mL of ethanol were put in a 300 mL-recovery flask. A reaction was conducted at 110C for 8 hours. The reaction solution was separated and extracted by adding ethyl acetate, and then the organic phase was washed with clean water and saturated saline and dried with sodium sulfate, and concentrated to obtain a crude product. The crude product was purified with silica gel chromatography (ethyl acetate/hexane (1/1)), and solids obtained were dried under reduced pressure to obtain 6.6g of white solids. The solids were identified as intermediate M5 by FD-MS (field desorption mass spectrometry) analysis.

Reference： [1]Patent: EP2423206,2012,A1 .Location in patent: Page/Page column 54

52
[ 5470-18-8 ]
[ 50548-43-1 ]
[ 1399050-10-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With triethylamine; In butan-1-ol;Reflux; Inert atmosphere;	2-chloro-3- nitropyridine (4.39 g, 27.7 mmol), dibenzo[¾,<i]furan-4-amine (5.58 g, 30.5 mmol), triethylamine (4.3 mL, 30.9 mmol), and butanol (90 mL) were mixed in a 250 mL round bottom flask. The reaction mixture was refluxed overnight under nitrogen. The solvent was evaporated, leaving an orange solid which was dried under vacuum. The solid was taken up in ethyl acetate, water was added and the layers were separated. The organic layer with washed with brine, dried over magnesium sulfate, filtered, and evaporated to a residue. The residue was purified on by column chromatography eluting with 10% ethyl acetate/hexanes followed by ethyl acetate (4.6 g, 54%).
	With triethylamine; In butan-1-ol;	Synthesis of N-(dibenzo[b,d]furan-4-yl)-3-nitropyridin-2-amine 2-chloro-3-nitropyridine (4.39 g, 27.7 mmol), <strong>[50548-43-1]dibenzo[b,d]furan-4-amine</strong> (5.58 g, 30.5 mmol), triethylamine (4.3 mL, 30.9 mmol), and butanol (90 mL) were mixed in a 250 mL round bottom flask. The reaction mixture was refluxed overnight under nitrogen. The solvent was evaporated, leaving an orange solid which was dried under vacuum. The solid was taken up in ethyl acetate, water was added and the layers were separated. The organic layer with washed with brine, dried over magnesium sulfate, filtered, and evaporated to a residue. The residue was purified on by column chromatography eluting with 10% ethyl acetate/hexanes followed by ethyl acetate (4.6 g, 54%).

Reference： [1]Patent: WO2012/121936,2012,A2 .Location in patent: Page/Page column 71
[2]Patent: US2012/228583,2012,A1

53
[ 50548-43-1 ]
[ 1399050-11-3 ]

Reference： [1]Patent: US2012/228583,2012,A1
[2]Patent: WO2012/121936,2012,A2

54
[ 50548-43-1 ]
[ 1399050-12-4 ]

Reference： [1]Patent: US2012/228583,2012,A1
[2]Patent: WO2012/121936,2012,A2

55
[ 1399050-09-9 ]
[ 50548-43-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogen;palladium(II) hydroxide; In ethanol;	Palladium hydroxide (20%, 0.75 g, 1.068 mmol) was added to a Parr hydrogenation bottle, and the bottle was purged with nitrogen. Next, 4-azidodibenzo[b,d]furan (7.39 g, 35.3 mmol) and 150 mL ethanol were added, and the reaction mixture was hydrogenated on Parr hydrogenator overnight. The reaction mixture was filtered through a pad of Celite, and the Celite was washed with dichloromethane. The filtrate was evaporated, and the residue was purified by column chromatography eluting with 50% dichloromethane/hexanes (5.58 g, 86%).
	palladium dihydroxide; In ethanol;	Synthesis of dibenzo[b,d]furan-4-amine Palladium hydroxide (20%, 0.75 g, 1.068 mmol) was added to a Parr hydrogenation bottle, and the bottle was purged with nitrogen. Next, 4-azidodibenzo[b,d]furan (7.39 g, 35.3 mmol) and 150 mL ethanol were added, and the reaction mixture was hydrogenated on Parr hydrogenator overnight. The reaction mixture was filtered through a pad of Celite, and the Celite was washed with dichloromethane. The filtrate was evaporated, and the residue was purified by column chromatography eluting with 50% dichloromethane/hexanes (5.58 g, 86%).

Reference： [1]Patent: WO2012/121936,2012,A2 .Location in patent: Page/Page column 71
[2]Patent: US2012/228583,2012,A1

56
[ 50548-43-1 ]
[ 1399050-13-5 ]

Reference： [1]Patent: WO2012/121936,2012,A2

57
[ 50548-43-1 ]
[ 578-57-4 ]
N-(2-methoxyphenyl)dibenzo[b,d]furan-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		The dibenzo [b, d] furan-4-amine 0.10molAnd sodium tert-butoxide 0.30 mol,Toluene 400 mL was added to the reaction flask,Stirred for 30 minutes,Nitrogen protection,Then 0.12 mol of 1-bromo-2-methoxybenzene was added,1.5 g of tris (dibenzylideneacetone) dipalladium,Finally, tri-tert-butylphosphine 4 g,And the temperature was raised to 100 C for 24 hours.After the reaction was completed, the reaction system was cooled,Water was added to terminate the reaction,filter,The filtrate was separated,Spin-dried toluene,A small amount of dichloromethane was added to dissolve the product after spinning,(Petroleum ether: dichloromethane = 3: 1 by volume)To give N- (2- methoxyphenyl) dibenzo [b, d] furan-4-amine (Intermediate D-1)(0.05mol, y = 50%).

Reference： [1]Patent: CN106083783,2016,A .Location in patent: Paragraph 0097; 0098; 0099; 0101

58
[ 50548-43-1 ]
2-(2-(dibenzo[b,d]furan-4-ylamino)phenyl)propan-2-ol [ No CAS ]

Reference： [1]Patent: CN106397398,2017,A
[2]Patent: CN107880058,2018,A
[3]Patent: CN108203417,2018,A

59
[ 50548-43-1 ]
5,13-dihydro-5,5-dimethylbenzofuran[3,2-c]acridine [ No CAS ]

Reference： [1]Patent: CN106397398,2017,A
[2]Patent: CN107880058,2018,A
[3]Patent: CN108203417,2018,A
[4]Patent: CN108203416,2018,A

60
[ 50548-43-1 ]
C₅₄H₃₈N₂O₂S [ No CAS ]

Reference： [1]Patent: CN106397398,2017,A

61
[ 50548-43-1 ]
[ 610-94-6 ]
methyl 2-(dibenzo[b,d]furan-4-ylamino)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 90℃; for 2h;Inert atmosphere;	50 g (0.272 mol) of <strong>[50548-43-1]4-aminodibenzofuran</strong>,87 g (0.408 mol) of methyl o-bromobenzoateAnd 32 g (0.326 mol) of sodium tert-butoxide were successively dissolved in 500 ml of toluene,Under nitrogen protection,5.46 ml (0.0027 mol) of tri-tert-butylphosphine was addedAnd 2.46 g (0.0027 mol) of Pd2 (dba) 3,Stirring up to 90 C,The reaction was carried out for about 2 hours.The resulting reaction solution was passed through a diatomaceous earth funnel,The filtrate was passed through a rotary evaporator to evaporate the solvent,55 g of 102-1 (yield: 65%).
60.9%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 115℃; for 24h;Inert atmosphere;	1) In a 250 ml three-neck flask, under the protection of nitrogen, add 0.03 mol of <strong>[50548-43-1]dibenzo[b,d]furan-4-amine</strong>, 0.04 mol of methyl 2-bromobenzoate, 0.06 mol of t-butoxide, 0.0015 Mol Pd2(dba)3, 0.0015 mol of tri-tert-butylphosphine, 150 ml of toluene, mixing and stirring, heating to 115 C., refluxing reaction for 24 hours, sample point plate, showing no <strong>[50548-43-1]dibenzo[b,d]furan-4-amine</strong> Residue, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was evaporated under reduced pressure until no fractions, over neutral silica gel column to give Intermediate 4-1, HPLC purity 99.3%, yield 60.9%;
60.9%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 115℃; for 12h;Inert atmosphere;	1) In a 250ml three-necked bottle, under nitrogen protection,0.03 mol of <strong>[50548-43-1]dibenzo[b,d]furan-4-amine</strong>, 0.04 mol of methyl 2-bromobenzoate,0.06 mol of sodium t-butoxide, 0.0015 mol of Pd2 (dba) 3, 0.0015 mol of tri-tert-butylphosphine,150 ml of toluene, stirred and stirred, heated to 115 C, refluxed for 12 hours, sampling plate,Showing no <strong>[50548-43-1]dibenzo[b,d]furan-4-amine</strong> remaining, the reaction is complete; naturally cooled to room temperature, filtered,The filtrate was evaporated to a fraction without distillation and passed through a neutral silica gel column to afford Intermediate 5-1, HPLC purity 99.3%, yield 60.9%;

60.9%

With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 115℃; for 12h;Inert atmosphere;

1) In a 250 ml three-necked flask, 0.03 mol of [50548-43-1]dibenzo[b,d]furan-4-amine was added in sequence under nitrogen protection.0.04 mol of methyl 2-bromobenzoate, 0.06 mol of sodium t-butoxide, 0.0015 mol of Pd2 (dba) 3,0.0015 mol of tri-tert-butylphosphine and 150 ml of toluene, mixed and stirred, heated to 115 C, and refluxed for 12 hours.Sampling the plate, showing no [50548-43-1]dibenzo[b,d]furan-4-amine remaining, the reaction is complete; naturally cooled to room temperature,Filtration, the filtrate was steamed to a fraction without distillation, and passed through a neutral silica gel column to obtain Intermediate 6-1.HPLC purity 99.3%, yield 60.9%

Reference： [1]Patent: CN106397398,2017,A .Location in patent: Paragraph 0041; 0042
[2]Patent: CN107880058,2018,A .Location in patent: Paragraph 0112; 0113
[3]Patent: CN108203417,2018,A .Location in patent: Paragraph 0123; 0124
[4]Patent: CN108203416,2018,A .Location in patent: Paragraph 0152-0154

62
[ 50548-43-1 ]
[ 23038-36-0 ]
C₂₄H₁₇NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 90 - 110℃; for 18h;Inert atmosphere;	Intermediate a2 (10.7 g, 30 mmol),Dibenzofuran-4-amino (6.4 g, 35 mmol),Bis (dibenzylideneacetone) palladium (578 mg, 0.9 mmol),Tri-tert-butylphosphine (182 mg, 0.9 mmol) andToluene (200 ml)Heated to 90 C under a stream of argon,After adding sodium tert-butoxide (115 mg, 1.2 mmol)Heated to 110 C under an argon atmosphere,The reaction was stirred for 18 hours.The reaction mixture was cooled to room temperature,Add water to separate.The solvent of the obtained organic layer was concentrated,The resulting solid was purified by silica gel column chromatography to give Intermediate b3 (5.9 g, 14.7 mmol) in 49% yield, MS[ESI +] m / z = 399.19 (theoretical 399.09).

Reference： [1]Patent: CN107286063,2017,A .Location in patent: Paragraph 0060; 0061; 0062

63
[ 553-86-6 ]
[ 50548-43-1 ]
10-(naphthalen-1-yl)anthracene-9-carboxaldehyde [ No CAS ]
C₄₅H₂₅NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With iodine; In tetrahydrofuran; at 80℃; for 24h;	1 · 34 g (10 mmol) of 2-coumaranone,1.83 g (10 mmol) of dibenzo [b, d] furan-4-amine,3.32 g (10 mmol) of 10- (naphthalen-1-yl) anthracene-9-carboxaldehyde and0.013 g (0.5 mmol) of iodine (I2) was dissolved in 150 mL of THF and then stirred at a temperature of 80 C for 24 hours. The reaction solution was cooled to room temperature.Then, the organic layer was extracted three times by using 60 mL of water and 60 mL of diethyl ether. The organic layer was dried by using magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to prepare 3.67 g (60%) of compound 1.

Reference： [1]Patent: CN107400139,2017,A .Location in patent: Paragraph 0420-0423

64
[ 50548-43-1 ]
C₃₄H₂₂BrNO [ No CAS ]

Reference： [1]Patent: KR2017/94020,2017,A

65
[ 50548-43-1 ]
C₅₈H₄₀N₂O [ No CAS ]

Reference： [1]Patent: KR2017/94020,2017,A

66
[ 50548-43-1 ]
C₅₈H₃₈N₂O₂ [ No CAS ]

Reference： [1]Patent: KR2017/94020,2017,A

67
[ 50548-43-1 ]
[ 92-66-0 ]
[ 1318338-47-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; for 6h;Inert atmosphere; Reflux;	Under an argon (Ar) atmosphere,20.0 g of <strong>[50548-43-1]4-aminodibenzofuran</strong>,25.4 g of 4-bromobiphenyl,0.6 g of (bis (dibenzylideneacetone) palladium (0) 0.9 g of tri-tert-butylphosphine,10.5 g of sodium tert-butoxide was added, And the mixture was refluxed in 500 mL of toluene for 6 hours.After air-cooling, water was added thereto, and the organic layer was separated, dried with magnesium sulfate,The solvent was distilled.The resulting crude productWas subjected to silica gel column chromatography (silica gel column chromatography) (Toluene / Hexane mixed solvent)To obtain 30.0 g (yield: 82%) of Intermediate A as a target product.

Reference： [1]Patent: KR2017/94020,2017,A .Location in patent: Paragraph 0227; 0228; 0230; 0231

68
[ 50548-43-1 ]
C₄₀H₂₉N₃O [ No CAS ]

Reference： [1]Patent: CN107880058,2018,A

69
[ 50548-43-1 ]
6-bromo-1,1-dimethyl-1H-phenalene [ No CAS ]
C₂₇H₂₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 90 - 105℃; for 5h;Inert atmosphere;	Compound 2 (30.6 g, 112 mmol), Compound 1 (20.5 g, 112 mmol), palladium acetate (1.56 g, 6.96 mmol),A mixture of BINAP (2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl) (8,67 g, 13.9 mmol) and 1.5 L of toluene in argon Under the conditions, the mixture was heated to 90 C., sodium tert-butoxide (16.7 g, 174 mmol) was added, and the mixture was stirred under argon at 105 C. for 5 hours. After cooling the reaction mixture at room temperature, water was added to separate the organic layer. The resulting organic layer was concentrated under reduced pressure and the resulting solid was used as a column. Chromatography gave compound 3 (29.44 g, 70% yield).

Reference： [1]Patent: CN107827758,2018,A .Location in patent: Paragraph 0115; 0116; 0117; 0118

70
[ 50548-43-1 ]
C₂₁H₁₆BrNO [ No CAS ]

Reference： [1]Patent: CN108203417,2018,A
[2]Patent: CN108203416,2018,A

71
[ 50548-43-1 ]
C₃₃H₂₄N₂O [ No CAS ]

Reference： [1]Patent: CN108203417,2018,A
[2]Patent: CN108203416,2018,A

72
[ 50548-43-1 ]
C₄₆H₃₃NO [ No CAS ]

Reference： [1]Patent: CN108203417,2018,A

73
[ 50548-43-1 ]
C₂₁H₁₉NO₂ [ No CAS ]

Reference： [1]Patent: CN108203416,2018,A

74
[ 50548-43-1 ]
C₃₉H₂₇BrN₂O [ No CAS ]

Reference： [1]Patent: CN108203416,2018,A

75
[ 50548-43-1 ]
C₃₉H₂₉BN₂O₃ [ No CAS ]

Reference： [1]Patent: CN108203416,2018,A

76
[ 50548-43-1 ]
C₂₂H₁₈⁽²⁾H₂Br₂ [ No CAS ]
C₄₆H₃₄⁽²⁾H₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 12h;Inert atmosphere; Reflux;	Compound 2-2 (11.15 g, 25 mmol)And dibenzofuran-4-aniline (9.14g, 50mmol)Add to a three-necked flask and stir to dissolve with 200 ml of anhydrous toluene.Nitrogen protection followed by the addition of Pd(dba) 2 (1.14 mg, 2 mmol) and sodium tert-butoxide(4.84 g, 50 mmol), followed by the addition of 10% tri-tert-butylphosphine toluene solution 7.6 mlThe reaction solution was stirred and refluxed for 12 hours.After cooling, the reaction solution was washed three times with 100 ml of water and dried over anhydrous sodium sulfate.Then the solvent is removed by evaporation.Residues with DCM/PE(1:15) after column purification,Obtained light white solid compound 2-3(6.98 g, yield 43%).

Reference： [1]Patent: CN109608342,2019,A .Location in patent: Paragraph 0199; 0200; 0201; 0206; 0207

77
[ 869340-02-3 ]
[ 50548-43-1 ]
C₄₆H₃₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 12h;Inert atmosphere; Reflux;	Comparative compound 1-2 (8.88 g, 20 mmol)And dibenzofuran-4 aniline (8.14 g, 44 mmol) was added to a three-necked flask.Stirred with 200 ml of anhydrous toluene, protected with nitrogen,Then add Pd(dba) 2 (690 mg, 1.2 mmol)And sodium tert-butoxide (3.84 g, 40 mmol),Then add 10% tri-tert-butylphosphine toluene solution 6.5mlThe reaction solution was stirred and refluxed for 12 hours, cooled, and the reaction mixture was washed three times with 100 ml of water.Dry over anhydrous sodium sulfate and then remove the solvent by evaporation.The residue was purified by DCM/PE (1:10).Obtained a light white solid compound C1-3(5.28 g, yield 45%).

Reference： [1]Patent: CN109608342,2019,A .Location in patent: Paragraph 0234; 0235; 0236; 0242; 0243

78
[ 50548-43-1 ]
C₂₂H₈⁽²⁾H₁₂Br₂ [ No CAS ]
C₄₆H₂₄⁽²⁾H₁₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 12h;Inert atmosphere; Reflux;	Compound 1-2 (9.12 g, 20 mmol) and dibenzofuran-4 aniline(8.14 g, 44 mmol) was added to a three-necked flask.Stirred with 200 ml of anhydrous toluene, protected with nitrogen,Then add Pd(dba) 2 (690 mg, 1.2 mmol)And sodium tert-butoxide (3.84 g, 40 mmol),Subsequently, 6.5 ml of a 10% tri-tert-butylphosphine toluene solution was added to reflux the reaction solution for 12 hours, cooled, and the reaction liquid was washed three times with 100 ml of water.Dry over anhydrous sodium sulfate and then remove the solvent by evaporation.Residues with DCM/PE (1:10)Purification through the column to obtain a light white solid compound 1-3(5.28 g, yield 40%).

Reference： [1]Patent: CN109608342,2019,A .Location in patent: Paragraph 0188; 0189; 0190; 0195; 0196

79
[ 50548-43-1 ]
C₃₀H₂₀BNO₄ [ No CAS ]

Reference： [1]Patent: CN109574926,2019,A

80
[ 50548-43-1 ]
C₅₁H₃₆N₂O₂ [ No CAS ]

Reference： [1]Patent: CN109574926,2019,A

81
[ 50548-43-1 ]
C₃₀H₁₈BrNO₂ [ No CAS ]

Reference： [1]Patent: CN109574926,2019,A

82
[ 89827-45-2 ]
[ 50548-43-1 ]
bis(dibenzofuran-4-yl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.8%	With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 105℃; for 24h;Inert atmosphere;	In a 250 ml three-necked flask, 0.01 mol of raw material O1 was added under nitrogen protection.0.012 mol of raw material P1, 150 ml of toluene were stirred and mixed.Then add 5×10-5 mol Pd2(dba)3, 5×10-5 mol P(Ph)3,0.03 mol of sodium tert-butoxide, heated to 105 C, refluxed for 24 hours, sampling plate,Show no bromine residue remaining, the reaction is complete; naturally cool to room temperature, filter,The filtrate is steamed to no fraction, and passed through a neutral silica gel column to obtain the target product intermediate B1;HPLC purity 99.03%, yield 74.8%;

Reference： [1]Patent: CN109574926,2019,A .Location in patent: Paragraph 0090; 0095-0097

83
[ 50548-43-1 ]
[ 2113-57-7 ]
N-([1,1'-biphenyl]-3-yl)dibenzo[b,d]furan-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 3h;	Dibenzo [b, d] furan-4-amine (dibenzo [b, d] furan-4-amine) (13 g, 1 eq) 3-bromophenyl (3-bromobiphenyl) (25 g, 1.2 eq), Pd 2 (dba) 3 (2.4 g, 0.03 eq), t-BuONa (12.5 g, 1.5 eq), t-Bu 3P (1.05 g, 0.06 eq), Toluene 400 ml are placed in a single round bottom flask (1-neck-R.B.F.) and stirred. (3h) MC / Hx = 1/5 N - ([1,1'-biphenyl] -3-yl) dibenzo [b, d] furan- (N - ([1,1'-biphenyl] -3-yl) dibenzo [b, d] furan-4-amine. (16 g, step yield = 73%)

Reference： [1]Patent: KR2019/58859,2019,A .Location in patent: Paragraph 0185-0187

84
[ 50548-43-1 ]
C₃₇H₃₃F₉O₃S [ No CAS ]
C₄₅H₄₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In toluene; at 100℃; for 8h;Inert atmosphere;	Intermediate 1-1 (2 g, 2.75 mmol), Intermediate 1-2 (603 mg, 3.3 mmol) and NaOtBu (tert-butoxysodium) (396 mg, 4.12 mmol) were placed in a 250 ml round bottom flask. 100 ml of Toluene was added under nitrogen, and the temperature was raised to 100 C. Pd (P (tBu3)) 2 (70 mg, 0.14 mmol) was added to a round bottom flask, and the mixture was stirred for 8 hours after blocking light.After lowering the temperature, the material was extracted using DCM (Dichloromethane) and water, and stirred with MgSO 4 and acid clay. After passing through silica gel, the solvent was removed. The material was separated by column chromatography (methyl chloride / Hexane).

Reference： [1]Patent: KR2019/96139,2019,A .Location in patent: Paragraph 0180-0183

85
[ 50548-43-1 ]
C₁₉H₁₉Br [ No CAS ]
C₅₀H₄₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 2h;Inert atmosphere; Reflux;	Add toluene solvent to the reaction flask, Intermediate 2-3 (26.18 g, 80 mmol), <strong>[50548-43-1]4-aminodibenzofuran</strong> (8.06g, 44mmol), sodium tert-butoxide (23.06g, 240mmol), after replacing with vacuum and nitrogen for three times, add Pd(OAc)2 (0.36g, 1.6mmol), replace it with vacuum and fill with nitrogen three times, and then add P(t-Bu)3 (6.4mL of 1.0M toluene solution, 6.4mmol), Nitrogen replacement was performed three more times, and the mixture was refluxed for 2 h under a nitrogen atmosphere. After the reaction was stopped, the mixture was cooled to room temperature, and filtered through celite to obtain a filtrate. The filtrate was concentrated, 20 mL of ethanol was added, and the solution was allowed to stand for recrystallization. The compound 315 (21.09 g, 78%) was obtained by filtration. The solid purity by HPLC was ? 99.9%.

Reference： [1]Patent: CN110845394,2020,A .Location in patent: Paragraph 0147-0151

86
[ 50548-43-1 ]
[ 162258-89-1 ]
C₂₈H₂₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; sodium t-butanolate In toluene at 100℃; for 5h; Inert atmosphere;	1.2 (2) Preparation of Intermediate 1-2 Intermediate 1-1 (2.4 g, 8.3 mmol) in a 250 mL flask in a nitrogen atmosphere,4-aminodibenzo[b,d]furan (1.52 g, 8.3 mmol),Bis(tri-tert-butylphosphine) palladium(0) (0.09 g, 0.17 mmol),Sodium tertbutoxide (1.2 g, 12.5 mmol) and toluene (50 mL) were added and stirred at 100° C. for 5 hours. When the reaction was completed, the mixture was cooled to room temperature, and the material was extracted using dichloromethane and water, treated with anhydrous magnesium sulfate to remove water, filtered, and concentrated under reduced pressure.The product was purified by column chromatography using normal hexane and dichloromethane, and then the solvent was removed. Recrystallized from dichloromethane and methanol to obtain Intermediate 1-2 (2.3 g, yield 71%).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2020/92211, 2020, A Location in patent: Paragraph 0161; 0166-0168

87
[ 50548-43-1 ]
[ 1257251-75-4 ]
C₃₇H₂₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 40℃; for 2h; Inert atmosphere;	5 5. Synthesis example of Sub 1-162 9-(3-bromophenyl)-9-phenyl-9H-fluorene (20.00 g, 50.34 mmol),dibenzo[b,d]furan-4-amine (13.83 g, 75.51 mmol),Pd2(dba)3 (2.30 g, 2.52 mmol),Add NaOtBu (14.51 g, 151.01 mmol) and 170 mL toluene.After that, nitrogen replacement is performed, and the temperature of the reactor is adjusted to 40°C.P(t-Bu)3 (2.04 ml, 5.03 mmol) was added, and when the reaction was completed after 2 hours,After removing the water in the reaction and filtration under reduced pressure,The organic layer was dried over MgSO4 and concentrated,The resulting compound was subjected to silica gel column and recrystallization to obtain 19.11 g of a product (yield: 76%).

Reference： [1]Current Patent Assignee: DUK SAN NEOLUX CO., LTD. - KR2021/100352, 2021, A Location in patent: Paragraph 0277-0279; 0307

88
[ 50548-43-1 ]
[ 1762-84-1 ]
N-(4-dibenzofuran)-4-[1,1'-biphenyl]-4-yl}aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene Inert atmosphere; Reflux;	5 Synthetic intermediate IM-6 Under Ar atmosphere, add 10.00g (54.6mmol) of 4-aminodibenzofuran, 0.94g (0.03eq, 1.6mmol) of Pd(dba)2, 5.25g (1.0eq , 54.6mmol) of NaOtBu, 273mL of toluene, 18.57g (1.1eq, 60.0mmol) of 4-bromo-1,1':4',1"-terphenyl and 1.10g (0.1eq, 5.5mmol) of tBu3P , Then heated, refluxed and stirred. After cooling to room temperature in the air, water was added to the reaction solution, and the organic layer was separately extracted. Toluene was added to the water layer, and the other organic layer was extracted. The organic layer was collected, washed with brine solution, It was dried with MgSO4. The MgSO4 was filtered, and the organic layer was concentrated. The crude product thus obtained was separated by silica gel column chromatography (using a mixture of hexane and toluene as an eluent) to obtain Intermediate IM-6 (17.74 g, product). Rate 79%).

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - CN113429403, 2021, A Location in patent: Paragraph 0305-0310

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P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
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

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. 50548-43-1 ] {[proInfo.proName]}

Quality Control of [ 50548-43-1 ]

Related Doc. of [ 50548-43-1 ]

Product Details of [ 50548-43-1 ]

Calculated chemistry of [ 50548-43-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 50548-43-1 ]

Application In Synthesis of [ 50548-43-1 ]

[ 50548-43-1 ] Synthesis Path-Upstream 1~13

[ 50548-43-1 ] Synthesis Path-Downstream 1~88

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Amines

Related Parent Nucleus of [ 50548-43-1 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 50548-43-1 ]

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[ 50548-43-1 ]