[ CAS No. 532924-25-7 ]

Name: 532924-25-7|(5-Chloro-2-nitrophenyl)boronic acid|98%
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Quality Control of [ 532924-25-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 532924-25-7 ]

Product Details of [ 532924-25-7 ]

CAS No. :	532924-25-7	MDL No. :	MFCD10696660
Formula :	C₆H₅BClNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PURYLRLRXKALOG-UHFFFAOYSA-N
M.W :	201.37 g/mol	Pubchem ID :	10214460
Synonyms :

Calculated chemistry of [ 532924-25-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.1
TPSA :	86.28 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.28
Log Po/w (WLOGP) :	-0.07
Log Po/w (MLOGP) :	0.59
Log Po/w (SILICOS-IT) :	-2.16
Consensus Log Po/w :	-0.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.1
Solubility :	1.58 mg/ml ; 0.00786 mol/l
Class :	Soluble
Log S (Ali) :	-2.69
Solubility :	0.41 mg/ml ; 0.00204 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.29
Solubility :	10.3 mg/ml ; 0.0513 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.23

Safety of [ 532924-25-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 532924-25-7 ]

* 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 [ 532924-25-7 ]

[ 532924-25-7 ] Synthesis Path-Downstream 1~24

1
[ 352-34-1 ]
[ 532924-25-7 ]
[ 1221425-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,2-dimethoxyethane; water at 60℃; for 2h; Inert atmosphere;	23 (Comparative Example 23); 5-Chloro-4 ' -fluorobiphenyl-2-amineTo water (2 mL) and dimethoxyethane (20 mL) , 5-chloro-2- nitrophenylboronic acid (3.27 g, 16.4 mmol), 1-fluoro-4-iodobenzene (3.65 g, 16.4 mmol), tetrakis (triphenylphosphine) palladium (0.95 g, 0.82 mmol) and potassium carbonate (6.81 g, 49.3 mmol) were added, and the mixture was stirred under a nitrogen atmosphere at 600C for 2 hours. After the reaction, the reaction mixture was cooled to room temperature and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL) and saturated brine (20 mL) , it was dried with sodium sulfate. The solvent was distilled off under reduced pressure to give 5-chloro-4 ' -fluoro-2- nitrobiphenyl as a crude product. The obtained compound was used for the subsequent reaction without further purification.

Reference： [1]Current Patent Assignee: EXELIXIS INC - WO2010/42626, 2010, A1 Location in patent: Page/Page column 46

2
[ 532924-25-7 ]
methyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-phenylpropanoate [ No CAS ]
methyl 2-(4-(5-chloro-2-nitrophenyl)-2-oxopyridin-1(2H)-yl)-3-phenylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In ethanol; toluene at 110℃; for 0.166667h; Microwave irradiation;	i-2.B Preparation of methyl 2-(4-(5-chloro-2-nitrophenyl)-2-oxopyridin-1(2H)-yl)-3-phenylpropanoate (i-2b) A degassed suspension of 1-lb (500 mg, 1.49 mmol), (5-chloro-2-nitrophenyl)boronicacid (329 mg, 1.64 mmol), potassium carbonate (206 mg, 1.49 mmol), and [1,1’-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (163 mg, 0.22 mmol) in EtOH:toluene (10 mL of a 4:1 mixture) was heated in a microwave reactor to 110 °C for 10 min. After cooling to rt, the reaction mixture was diluted with EtOAc and filtered through a colunm of Celite, which was rinsed with additional portions of EtOAc. The combined organics were dried(Na2SO4), filtered and concentrated, and the resulting crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-30% EtOAc/hexanes as eluent) to afford the title compound as a white solid. m/z (ES) 413 (MH)+.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2014/160592, 2014, A2 Location in patent: Page/Page column 41

3
[ 532924-25-7 ]
2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-phenylpropanoic acid [ No CAS ]
2-(4-(5-chloro-2-nitrophenyl)-2-oxopyridin-1(2H)-yl)-3-phenylpropanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; sodium phosphate In 1-methyl-pyrrolidin-2-one at 90℃; for 16h;	i-2.A Preparation of 2-(4-(5-chloro-2-nitrophenyl)-2-oxopyridin-1(2H)-yl)-3-phenylpropanoic acid (i-2a) A degassed suspension of i-ic (100 mg, 0.3 10 mmol), (5-chloro-2-nitrophenyl)boronic acid (94 mg, 0.466 mmol), potassium phosphate, tribasic (0.78 mL of a 1M aq. solution, 0.778 mmol), and 1,1 ‘-bis(di-tert-butylphosphino)ferrocenepalladium dichloride (20 mg, 0.031 mmol)in NMP (2.6 mL) was heated to 90 °C. After 16 h, the reaction mixture was cooled to rt, and partitioned between EtOAc and water. The layers were separated, the aq. layer was acidified with 1M HC1 and extracted with EtOAc. The combined organics were washed with water and brine, dried (MgSO4), filtered and concentrated to afford the title compound i-2a as a crude brown solid. m/z (ES) 399 (MH)+.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2014/160592, 2014, A2 Location in patent: Page/Page column 40; 41

4
[ 532924-25-7 ]
tert-butyl 4-(2-(5-bromopyridin-2-yl)-3-phenylpropanamido)benzoate [ No CAS ]
tert-butyl 4-(2-(5-(5-chloro-2-nitrophenyl)pyridin-2-yl)-3-phenylpropanamido)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In tetrahydrofuran; water at 100℃; for 1h; Microwave irradiation; Sealed tube; Inert atmosphere;	1.3; 2.3 Step 3. fert-Butyl 4-(2-(5 -(5 -chloro-2-nitrophenyl)pyridin-2-yl)-3 -phenylpropanamido) benzoate(l-C) Step 3. fert-Butyl 4-(2-(5 -(5 -chloro-2-nitrophenyl)pyridin-2-yl)-3 -phenylpropanamido) benzoate(l-C) A mixture of tert-butyl 4-(2-(5-bromopyridin-2-yl)-3 -phenylpropanamido) benzoate (1-B) (0.475 g, 0.987 mmol), (5-chloro-2-nitrophenyl)boronic acid (0.397 g, 1.973 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.16 g, 0.197 mmol) in THF(5 mL) was added potassium phosphate tribasic aqueous solution (2 mL, 4 mmol, 2M) in a microwave tube. The tube was sealed, degassed and refilled with N2. The mixture was heated at 100°C by microwave for 1 hour. The reaction mixture was diluted with water, extracted with EtOAc, and the organic layers were combined and washed with brine and dried over Na2S04. Solvent was removed in vacuo. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane to give product 1-C. 1H NMR (500 MHz, CDC13) δ: 1.66 (9H, s), 3.32 (1 H, dd), 3.60 (1 H, dd), 4.10 (1 H, m), 7.05 (2 H, d), 7.10-7.24 (4H,m), 7.42 (1 H, d), 7.58-7.63 (4H, m), 7.95 (2 H, d), 8.03 (1 H, d), 8.59 (1 H, s), 10.00 (1 H, s).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2015/183709, 2015, A1 Location in patent: Page/Page column 34

5
[ 532924-25-7 ]
2-(1-(5-bromopyridin-2-yl)-2-phenylethyl)-5-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole [ No CAS ]
2-(1-(5-(5-chloro-2-nitrophenyl)pyridin-2-yl)-2-phenylethyl)-5-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In tetrahydrofuran; water at 100℃; for 1h; Inert atmosphere; Microwave irradiation;	7.4 Step 4. 2-(l -(5-(5-chloro-2-nitrophenyl)pyridin-2-yl)-2-phenylethyl)-5-fluoro- 1 -((2- (trimethylsilyl)ethoxy)methyl)-lH-benzo[dlimidazole) (3-D): A reaction mixture of 2-(l-(5- Bromopyridin-2-yl)-2-phenylethyl)-5 -fluoro- 1 -((2-(trimethylsilyl)ethoxy)methyl) - 1 H- benzo[d]imidazole (3-C) (150 mg, 0.28 mmol), PdCl2(dppf) (62.5 mg, 0.085 mmol), (5-chloro- 2-nitrophenyl)boronic acid (86 mg, 0.427 mmol) and potassium phosphate tribasic aq. solution (0.57 ml, 1.14 mmol, 2M) in THF (2 ml) was degassed and refilled with N2. It was heated at 100°C for 1 hour by microwave. The reaction mixture was diluted with water, extracted with EtOAc, the organic was washed with brine, dried over Na2S04. Solvent was removed in vacuo. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane to give the product (3-D). 1H NMR (500 MHz, CDC13) δ: -0.097 (9H, s), 0.79-0.64 (2H, m), 3.30- 3.18 (2H, m), 3.62 (1H, m), 3.89 (1H, m), 4.90 (1H, m), 5.27 (1H, dd), 5.45 (1H, dd), 7.03 (1H, m), 7.23-7.12 (6H, m), 7.31 (1H, m), 7.36 (1H, m), 7.60-7.49 (3H, m), 7.79 (1H, m), 7.96 (1H, d,) 8.46 (1H, s).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2016/18701, 2016, A1 Location in patent: Page/Page column 35; 36

6
[ 532924-25-7 ]
2-(1-(5-bromopyridin-2-yl)-2-phenylethyl)-5-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole [ No CAS ]
4-chloro-2-(6-(1-(5-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2-phenylethyl)pyridin-3-yl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; water / 1 h / 100 °C / Inert atmosphere; Microwave irradiation 2: tin(II) chloride dihdyrate; ethanol / ethyl acetate / 3 h / 50 °C

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2016/18701, 2016, A1

7
[ 2730-62-3 ]
[ 532924-25-7 ]
[ 357274-88-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; 2-(dicyclohexylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole In 1,4-dioxane; water at -100 - 100℃; for 5h; Autoclave;	25 General procedure: (3a, 5a) General procedure: The reaction was carried out in an autoclave containing a 10 mL Teflon reaction tube. Pd(PPh3)2Cl2 (1 mol %), B (2 mol %) and a magnetic stir bar were placed in the tube, followed by addition of arylboronic acid (1 mmol), NaHCO3 (2 mmol), 1,4-dioxane (2 mL) and water (0.5 mL). the tube was capped with a stopper. The autoclave was cooled down to -100 °C by liquid nitrogen, and 2-chloro-3,3,3-trifluoroprop-1-ene (2, 18 mmol) was added to the reaction. Finally the autoclave was heated in an oil bath at 100 °C for 5 h. After the reaction, the autoclave was then cooled to room temperature and vented to discharge the excessive 2,3,3,3-tetrafluoropropylene carefully. Water (60 mL) was added, and the product was extracted with dichloromethane (3*15 mL). The organic layers were washed with brine (30 mL), dried over Na2SO4, and the organic solvent was evaporated by a rotary evaporator under atmospheric pressure. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate as eluents).

Reference： [1]Li, Yang; Zhao, Bo; Dai, Kun; Tu, Dong-Huai; Wang, Bo; Wang, Yao-Yu; Liu, Zhao-Tie; Liu, Zhong-Wen; Lu, Jian [Tetrahedron, 2016, vol. 72, # 37, p. 5684 - 5690]

8
[ 504424-70-8 ]
[ 532924-25-7 ]
5-(5-chloro-2-nitrophenyl)-1-phenyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 40 - 80℃; for 12h; Inert atmosphere;	2.2 Synthesis of 5-(5-chloro-2-nitrophenyl)-1-phenyl-1H-indole Nitrogen gas stream under the above obtained from 5-bromo-1-phenyl-1H-indole (20 g, 73.49 mmol), 5-chloro-2-nitrophenylboronic acid (17.78g, 88.18 mmol), K 2 CO 3 (30.47 g, 220.47 mmol) and THF / H2O into the (400ml / 100 ml) was stirred. In 40 °C Pd(PPh3)4 into the (2.54 g, 2.204mmol) it was stirred under reflux at 80 °C for 12 hours.After completion of the reaction extracted with dichloromethane, and the organic layer is MgSO4was filtered off and dried in a vacuum.The filtered organic layer was evaporated under reduced pressure to a back by column chromatography the desired compound 5- (5-chloro-2- nitrophenyl) -1-phenyl-1H-indole (18 g,yield: 72%) was obtained.
72%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 40 - 80℃; for 12h; Inert atmosphere;	1.1 Synthesis of 5-(5-chloro-2-nitrophenyl)-1-phenyl-1H-indole A stream of nitrogen under 5-bromo-1-phenyl-1H-indole (20 g, 73.49 mmol), 5-chloro-2-nitrophenylboronic acid (17.78g, 88.18 mmol), K2CO3 (30.47 g, 220.47 mmol) and THF/H2O (400ml / 100 ml) were put into a stirred. At 40 into the Pd (PPh3) 4 (2.54 g, 2.204mmol) was stirred under reflux at 80 for 12 hours. After completion of the reaction, which was then extracted with dichloromethane. The organic layer was dried over MgSO4 filtered under reduced pressure. The filtered organic layer was evaporated under reduced pressure to a back by column chromatography the desired compound 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indole (18g, Yield: 72%) was obtained.
72%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; for 12h;	2.2 Step 2 Synthesis of 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indole 20 g, 73.49 mmol), 5-chloro-2-nitrophenylboronic acid (17.78 g, 88.18 mmol), K2CO3 (30.47 g, 220.47 mmol) and THF / H2O (400 ml / 100 ml) was added and stirred. At 40 ° CPd (PPh3) 4 (2.54 g, 2.204 mmol) was added and the mixture was refluxed and stirred at 80 for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO4 and filtered under reduced pressure. The filtrated organic layer was distilled under reduced pressure, and then the target compound, 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indole (18 g, yield: 72%) was obtained by column chromatography

Reference： [1]Current Patent Assignee: DOOSAN CORP. - KR2015/38811, 2015, A Location in patent: Paragraph 0165-0167
[2]Current Patent Assignee: DOOSAN CORP. - KR2015/8658, 2015, A Location in patent: Paragraph 0113-0115
[3]Current Patent Assignee: DOOSAN CORP. - KR101599586, 2016, B1 Location in patent: Paragraph 0135-0137

9
[ 532924-25-7 ]
7-chloro-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere

Reference： [1]Current Patent Assignee: DOOSAN CORP. - KR2015/38811, 2015, A
[2]Current Patent Assignee: DOOSAN CORP. - KR2015/8658, 2015, A

10
[ 532924-25-7 ]
3-phenyl-7-(9-phenyl-9H-carbazol-3-yl)-3,10-dihydropyrrolo[3,2-a]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydroxide / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: DOOSAN CORP. - KR2015/38811, 2015, A

11
[ 532924-25-7 ]
C₃₅H₂₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydroxide / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: DOOSAN CORP. - KR2015/38811, 2015, A

12
[ 532924-25-7 ]
C₂₀H₁₂BrN [ No CAS ]
C₂₆H₁₅ClN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 110℃; for 3h; Inert atmosphere;	4.3 <Step 3> Synthesis of D1 Under a nitrogen stream A2, 3.7g, (10.8 mmol), 5-chloro-2-nitrophenylboronic acid, 2.2g (10.8 mmol), 0.6g (5 mol%) of Pd (PPh3) 4, and potassium carbonate, 4.5g ( put Toluene / H2O / Ethanol of 32.3 mmol) and 80ml / 40ml / 40ml was stirred for 3 hours at 110 °C. After the reaction, using a methylene chloride The organic layer was separated using MgSO4 was removed [0182] water. The solvent of the organic layer was purified by column chromatography to give the title compound, D1, (3.7g, 8,7mmol, yield 81%).

Reference： [1]Current Patent Assignee: DOOSAN CORP. - KR2016/76355, 2016, A Location in patent: Paragraph 0166; 0179-0182

13
[ 532924-25-7 ]
7-chloro-3,10-diphenyl-3,10-dihydropyrrolo[3,2-a]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: copper; potassium carbonate / nitrobenzene / 24 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: DOOSAN CORP. - KR2015/8658, 2015, A

14
[ 532924-25-7 ]
7-(9H-carbazol-3-yl)-3,10-diphenyl-3,10-dihydropyrrolo[3,2-a]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: copper; potassium carbonate / nitrobenzene / 24 h / Inert atmosphere; Reflux 4: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: DOOSAN CORP. - KR2015/8658, 2015, A

15
[ 532924-25-7 ]
3,10-diphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,10-dihydropyrrolo[3,2-a]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: copper; potassium carbonate / nitrobenzene / 24 h / Inert atmosphere; Reflux 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: DOOSAN CORP. - KR2015/8658, 2015, A

16
[ 532924-25-7 ]
C₅₆H₃₇N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: copper; potassium carbonate / nitrobenzene / 24 h / Inert atmosphere; Reflux 4: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 5: copper; sodium sulfate; potassium carbonate / nitrobenzene / 12 h / 190 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: DOOSAN CORP. - KR2015/8658, 2015, A

17
[ 532924-25-7 ]
ethyl 3-bromo-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate [ No CAS ]
ethyl 3-(5-chloro-2-nitrophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In tetrahydrofuran; water at 100 - 120℃; for 2h; Microwave irradiation;	1.1 Step 1: ethyl 3-(5-chloro-2-nitrophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate Step 1: Ethyl 3 (5chloro2nitrophenyl (1C)A microwave vial was charged with ethyl 3 bromo-6, 7dihydro5Wcyclopenta[bipyridine7 carboxylate (1A) (1.0 g, 3.7 rnmol), (5-cliloro.-2-nitrophenyi)boronic acid (i-B) (1.49 g, 7.40 mmol), 1,1’ -.bis(diphenylphosphino)ferrocene-.palladiumll)di chloride di chloromethane complex (0.605 g, 0.740 mmol), THF (5 mL), and 2M aq. potassium phosphate tribasic (7.4 mL, 14.8 mmol). The reaction mixture ‘as heated at 100°C under microwave irradiation for 60 mm Afterthis time, the reaction was not complete by LCMS analysis. More (5chloro-.2- nitrophenyi)boronic acid (1491 g, 7.40 mmoi) was added, and the reaction mixture was heated at 120°C for 60 mm. The mixture was cooled, filtered through celite, and the filtrates were partitioned between EtOAc and water. The organic phase was washed with brine, dried over sodium sulfate, and concentrated. Flash chromatography (80g Si02, 0-400% EtOAc in hexane)gave the title compound. MS (ESI) rn/z 349.22 (M±H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2016/118403, 2016, A1 Location in patent: Page/Page column 35

18
[ 532924-25-7 ]
C₂₁H₁₅F₃N₂O₃S [ No CAS ]
C₂₆H₁₈ClN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2020/52224, 2020, A1 Location in patent: Paragraph 0208

19
[ 532924-25-7 ]
[ 1308677-09-9 ]
C₁₇H₁₂ClN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium carbonate In toluene at 75 - 90℃; Inert atmosphere;	1.2 (2) A 1 liter three-necked flask equipped with magnetic stirring. After nitrogen replacement, 20.35g (0.189mol) of sodium carbonate, 24.5g (0.1mol) of (5-chloro-2-nitrophenyl)boronic acid and 100ml of toluene were added in sequence. After replacing with nitrogen again, 5 g (7 mmol) of Pd132 were sequentially added. After the addition, heat to 80°C. Begin to add dropwise to the solution consisting of 27.39g of compound P1-1 (0.11mol) and 100ml of toluene, and the temperature was controlled at 75-90°C. After the reaction, the organic phase was separated, extracted, dried, column chromatography, and the solvent was spin-dried to obtain 25.02 g of yellow solid P1-2 with a yield of 77%.

Reference： [1]Current Patent Assignee: BEIJING YUNJI TECHNOLOGY CO LTD (YUNJI PHOTONICS) - CN111718342, 2020, A Location in patent: Paragraph 0044-0045; 0048

20
[ 532924-25-7 ]
C₁₈H₁₀ClNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere 2: triethyl phosphite / 145 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN113501824, 2021, A

21
[ 532924-25-7 ]
C₃₆H₂₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere 2: triethyl phosphite / 145 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 12 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN113501824, 2021, A

22
[ 532924-25-7 ]
C₅₀H₃₀N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere 2: triethyl phosphite / 145 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 12 h / 80 °C / Inert atmosphere 4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / o-xylene / 12 h / 120 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN113501824, 2021, A

23
[ 105906-36-3 ]
[ 532924-25-7 ]
2-(5-chloro-2-nitrophenyl)dibenzo[b,e][1,4]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere;	6.1 (1) Synthesis of intermediate 325-1 Add the intermediate 2-bromodibenzo[b,e][1,4]dioxin (16.15g, 61.4mmol), 295-2 (12.36g, 61.4mmol), into a 500mL reaction flask, tetrakis(triphenylphosphine)palladium (5mol%), K2CO3 (17.0g, 122.8mmol), 1,4-dioxane (200mL) and water (50mL). The reaction system was heated to 90 °C and reacted for 12 hours under the protection of nitrogen. After the completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried with anhydrous magnesium sulfate, concentrated and recrystallized, and the crude product obtained was passed through a silica gel column to obtain Intermediate 325-1 (13.56 g, yield 65%).

Reference： [1]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN113501824, 2021, A Location in patent: Paragraph 0072-0075

24
[ 532924-25-7 ]
C₁₉H₁₃BrN₂ [ No CAS ]
C₂₅H₁₆ClN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere;	1.2 (2) Synthesis of Intermediate 295-3 Intermediate 295-1 (21.44g, 61.4mmol), 295-2 (12.36g, 61.4mmol), tetrakis(triphenylphosphine)palladium (5mol%) were added to a 500mL reaction flask, K2CO3 (17.0 g, 122.8 mmol), 1,4-dioxane (200 mL) and water (50 mL). The reaction system was heated to 90 °C and reacted for 12 hours under nitrogen protection. After the completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried with anhydrous magnesium sulfate, concentrated, and the crude product obtained by recrystallization was passed through a silica gel column to obtain Intermediate 295-3 (18.30 g, yield 70%).

Reference： [1]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN113501824, 2021, A Location in patent: Paragraph 0048; 0052-0054

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P378
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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.
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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.
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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:
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P401
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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
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H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
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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
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
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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
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H332	Harmful if inhaled
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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
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H370	Causes damage to organs
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H372	Causes damage to organs through prolonged or repeated exposure
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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. 532924-25-7 ]

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[ 532924-25-7 ] Synthesis Path-Downstream 1~24

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Organoboron

Aryls

Chlorides

Nitroes

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[ 532924-25-7 ]