[ CAS No. 17613-40-0 ] {[proInfo.proName]}

Name: 17613-40-0|6-Bromophenanthridine|98%
Brand: Ambeed
SKU: A247801
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Quality Control of [ 17613-40-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17613-40-0 ]

SDS Specification

Alternatived Products of [ 17613-40-0 ]

Product Details of [ 17613-40-0 ]

CAS No. :	17613-40-0	MDL No. :	MFCD09836427
Formula :	C₁₃H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GMWZNUNCVLSUGP-UHFFFAOYSA-N
M.W :	258.11	Pubchem ID :	10956232
Synonyms :

Calculated chemistry of [ 17613-40-0 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	14
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.95
TPSA :	12.89 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) :	-4.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.58
Log Po/w (XLOGP3) :	4.46
Log Po/w (WLOGP) :	4.15
Log Po/w (MLOGP) :	3.72
Log Po/w (SILICOS-IT) :	4.17
Consensus Log Po/w :	3.82

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.94
Solubility :	0.00296 mg/ml ; 0.0000115 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.45
Solubility :	0.00916 mg/ml ; 0.0000355 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.23
Solubility :	0.000151 mg/ml ; 0.000000586 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.8

Safety of [ 17613-40-0 ]

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

Application In Synthesis of [ 17613-40-0 ]

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

Upstream synthesis route of [ 17613-40-0 ]
Downstream synthetic route of [ 17613-40-0 ]

[ 17613-40-0 ] Synthesis Path-Upstream 1~8

1
[ 173379-08-3 ]
[ 15679-03-5 ]
[ 17613-40-0 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296

2
[ 1015-89-0 ]
[ 17613-40-0 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 2, p. 169 - 174
[2] Journal of the Chemical Society, 1934, p. 104,106[3] Journal of the Chemical Society, 1935, p. 1405,1406

3
[ 173379-08-3 ]
[ 17613-40-0 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296

4
[ 3128-77-6 ]
[ 17613-40-0 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296

5
[ 90-41-5 ]
[ 17613-40-0 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 2, p. 169 - 174

6
[ 40484-36-4 ]
[ 17613-40-0 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 2, p. 169 - 174

7
[ 23088-28-0 ]
[ 17613-40-0 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 2, p. 169 - 174

8
[ 173379-08-3 ]
[ 15679-03-5 ]
[ 17613-40-0 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296

[ 17613-40-0 ] Synthesis Path-Downstream 1~49

1
[ 27578-60-5 ]
[ 17613-40-0 ]
phenanthridin-6-yl-(2-piperidino-ethyl)-amine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1934,p. 104,106
Journal of the Chemical Society,1935,p. 1405,1406

2
[ 2038-03-1 ]
[ 17613-40-0 ]
(2-morpholino-ethyl)-phenanthridin-6-yl-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 302

3
[ 1015-89-0 ]
[ 17613-40-0 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 169 - 174
[2]Journal of the Chemical Society,1934,p. 104,106
Journal of the Chemical Society,1935,p. 1405,1406

4
[ 17613-40-0 ]
[ 108-00-9 ]
N,N-dimethyl-N'-phenanthridin-6-yl-ethylenediamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 302

5
[ 17613-40-0 ]
[ 100-36-7 ]
[ 108-95-2 ]
[ 3340-87-2 ]

Reference： [1]Journal of the Chemical Society,1959,p. 1563,1567

6
[ 17613-40-0 ]
[ 100-36-7 ]
N,N-diethyl-N'-phenanthridin-6-yl-ethylenediamine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1934,p. 104,106
Journal of the Chemical Society,1935,p. 1405,1406

7
[ 17613-40-0 ]
[ 108-95-2 ]
[ 3340-87-2 ]

Reference： [1]Journal of the Chemical Society,1934,p. 104,106
Journal of the Chemical Society,1935,p. 1405,1406

8
[ 17613-40-0 ]
[ 229-87-8 ]

Reference： [1]Journal of the Chemical Society,1948,p. 1284,1290

9
[ 17613-40-0 ]
[ 17612-91-8 ]
[ 138118-78-2 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 169 - 174

10
[ 110-89-4 ]
[ 17613-40-0 ]
[ 33692-83-0 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 2295 - 2296

11
[ 17613-40-0 ]
[ 64-17-5 ]
[ 78288-66-1 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 2295 - 2296

12
[ 17613-40-0 ]
[ 143-33-9 ]
[ 2176-28-5 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 2295 - 2296

13
[ 17613-40-0 ]
[ 1015-89-0 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 2295 - 2296

14
[ 173379-08-3 ]
[ 15679-03-5 ]
[ 17613-40-0 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 2295 - 2296

15
[ 173379-08-3 ]
[ 17613-40-0 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 2295 - 2296

16
[ 3128-77-6 ]
[ 17613-40-0 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 2295 - 2296

17
[ 40484-36-4 ]
[ 17613-40-0 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 169 - 174

18
[ 23088-28-0 ]
[ 17613-40-0 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 169 - 174

19
[ 90-41-5 ]
[ 17613-40-0 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 169 - 174

20
[ 17613-40-0 ]
N-benzyl-N',N'-dimethyl-N-phenanthridin-6-yl-ethylenediamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 302

21
[ 17613-40-0 ]
C₁₅H₁₂BN₃O₂ [ No CAS ]
C₂₈H₁₈N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 80 - 90℃;	Into the Sub 1 (2) (5.5g, 20mmol) in a round bottom flask, Sub 2-9 (5.2g, 20mmol), Pd(PPh3)4 (0.7g, 0.6mmol), NaOH (2.4g, 60mmol), put the THF (60 mL), water (30mL). Then heated to reflux while 80 ~ 90 . After completion of reaction, diluted with distilled water at room temperature and extracted with methylene chloride and water. The resulting compound was concentrated by drying the organic layer with MgSO4 silicagel column and recrystallized to obtain 6.1g 1-2. (Yield: 74%)

Reference： [1]Patent: KR2015/124000,2015,A .Location in patent: Paragraph 0131

22
[ 17613-40-0 ]
4,6-diphenyl-2-[4'-(2-pyridyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3-yl]-1,3,5-triazine [ No CAS ]
C₄₅H₂₉N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.3%	With palladium diacetate; potassium carbonate; XPhos; In tetrahydrofuran; water; at 60 - 70℃; for 18.0h;Inert atmosphere;	Under a nitrogen stream,Compound (B2) (1.18 g, 2.00 mmol) obtained in Synthesis Example 2,6-Bromophenanthridine (Synthesis Example J. Org. Chem. 2010, 75, 4848) (0.619 g, 2.40 mmol),Palladium acetate (23 mg, 0.100 mmol),2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl (95 mg, 0.200 mmol),And tetrahydrofuran (20 mL) were added to a 100 mL four-necked flask and heated to 60 C.A 20% aqueous solution of K 2 CO 3 (3.2 mL, 6.00 mmol) was added dropwise thereto over 5 minutes,And the mixture was stirred at 70 C. for 18 hours.After cooling to room temperature,Water (20 mL) was added to the reaction mixture,Precipitates were collected by filtration. The collected precipitate was washed successively with pure water, methanol and hexane to obtain a gray powder. The obtained gray powder was purified by recrystallization with toluene to obtain an off-white powder (yield 1.04 g, yield 81.3%, LC purity 98.82%) of the objective compound (A2)

Reference： [1]Patent: JP2017/132734,2017,A .Location in patent: Paragraph 0064

23
[ 17613-40-0 ]
[ 27825-35-0 ]
C₃₇H₂₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 180℃; for 24.0h;Inert atmosphere;	General procedure: Intermediate products (C),The substituent compound (A-x, x is a halogen element), Na (t-Bu) and Pd2 (dba) 3 were suspended in toluene, and P (t-Bu) 3 was added thereto and stirred under reflux for 24 hours under a stream of nitrogen.The mixture was then extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration.Subsequently, the organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane (1: 1 v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain an organic compound.

Reference： [1]Patent: KR101676416,2016,B1 .Location in patent: Paragraph 0148-0152

24
[ 17613-40-0 ]
[ 1628-77-9 ]
C₂₅H₁₅N₃O₂S [ No CAS ]

Reference： [1]Patent: US2018/212158,2018,A1 .Location in patent: Paragraph 0551

25
[ 854952-58-2 ]
[ 17613-40-0 ]
6-(9-phenyl-9H-carbazol-3-yl)phenanthridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium diacetate; potassium carbonate; In toluene; at 80℃; for 48.0h;	28.9 g (43.3 mmol) of <strong>[17613-40-0]6-bromophenanthridine</strong> and 13.7 g (48 mmol) of 9-phenyl-9H-carbazole-3-boronic acid are dissolved in 80 ml of toluene and degassed. 281 ml of a degassed solution of 2 M K2CO3 and 2.5 g (2.2 mmol) of Pd(OAc)2 are added. The reaction mixture is then stirred under a protective gas atmosphere at 80 C. for 48 h. The cooled solution is supplemented with toluene, washed repeatedly with water, dried and concentrated. The product is purified via column chromatography on silica gel with toluene/heptane (1:2) and finally sublimed under high vacuum (p=5*10-7 mbar). The purity is 99.9%. Yield: 28 g (31 mmol), 80% of theory.

Reference： [1]Patent: US2018/282295,2018,A1 .Location in patent: Paragraph 0145; 0146

26
[ 17613-40-0 ]
9-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [ No CAS ]
C₄₀H₂₅N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With palladium diacetate; potassium carbonate; In toluene; at 80℃; for 48.0h;	General procedure: 28.9 g (43.3 mmol) of <strong>[17613-40-0]6-bromophenanthridine</strong> and 13.7 g (48 mmol) of 9-phenyl-9H-carbazole-3-boronic acid are dissolved in 80 ml of toluene and degassed. 281 ml of a degassed solution of 2 M K2CO3 and 2.5 g (2.2 mmol) of Pd(OAc)2 are added. The reaction mixture is then stirred under a protective gas atmosphere at 80 C. for 48 h. The cooled solution is supplemented with toluene, washed repeatedly with water, dried and concentrated. The product is purified via column chromatography on silica gel with toluene/heptane (1:2) and finally sublimed under high vacuum (p=5*10-7 mbar). The purity is 99.9%. Yield: 28 g (31 mmol), 80% of theory.

Reference： [1]Patent: US2018/282295,2018,A1 .Location in patent: Paragraph 0145; 0146; 0147

27
[ 17613-40-0 ]
[ 1346010-98-7 ]
C₄₉H₃₃N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With palladium diacetate; potassium carbonate; In toluene; at 80℃; for 48.0h;	General procedure: 28.9 g (43.3 mmol) of <strong>[17613-40-0]6-bromophenanthridine</strong> and 13.7 g (48 mmol) of 9-phenyl-9H-carbazole-3-boronic acid are dissolved in 80 ml of toluene and degassed. 281 ml of a degassed solution of 2 M K2CO3 and 2.5 g (2.2 mmol) of Pd(OAc)2 are added. The reaction mixture is then stirred under a protective gas atmosphere at 80 C. for 48 h. The cooled solution is supplemented with toluene, washed repeatedly with water, dried and concentrated. The product is purified via column chromatography on silica gel with toluene/heptane (1:2) and finally sublimed under high vacuum (p=5*10-7 mbar). The purity is 99.9%. Yield: 28 g (31 mmol), 80% of theory.

Reference： [1]Patent: US2018/282295,2018,A1 .Location in patent: Paragraph 0145; 0146; 0147

28
[ 17613-40-0 ]
C₄₅H₄₂BNO₂ [ No CAS ]
C₅₂H₃₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With palladium diacetate; potassium carbonate; In toluene; at 80℃; for 48.0h;	General procedure: 28.9 g (43.3 mmol) of <strong>[17613-40-0]6-bromophenanthridine</strong> and 13.7 g (48 mmol) of 9-phenyl-9H-carbazole-3-boronic acid are dissolved in 80 ml of toluene and degassed. 281 ml of a degassed solution of 2 M K2CO3 and 2.5 g (2.2 mmol) of Pd(OAc)2 are added. The reaction mixture is then stirred under a protective gas atmosphere at 80 C. for 48 h. The cooled solution is supplemented with toluene, washed repeatedly with water, dried and concentrated. The product is purified via column chromatography on silica gel with toluene/heptane (1:2) and finally sublimed under high vacuum (p=5*10-7 mbar). The purity is 99.9%. Yield: 28 g (31 mmol), 80% of theory.