[ CAS No. 1313519-78-6 ] {[proInfo.proName]}

Name: 1313519-78-6|2-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|97%
Brand: Ambeed
SKU: A252374
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Quality Control of [ 1313519-78-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1313519-78-6 ]

SDS Specification

Alternatived Products of [ 1313519-78-6 ]

Product Details of [ 1313519-78-6 ]

CAS No. :	1313519-78-6	MDL No. :	MFCD23701649
Formula :	C₁₇H₂₀BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QMKLHPJUOGNMPU-UHFFFAOYSA-N
M.W :	281.16	Pubchem ID :	67122029
Synonyms :

Calculated chemistry of [ 1313519-78-6 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.35
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	86.15
TPSA :	31.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.5
Log Po/w (WLOGP) :	3.05
Log Po/w (MLOGP) :	1.89
Log Po/w (SILICOS-IT) :	2.9
Consensus Log Po/w :	2.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.08
Solubility :	0.0234 mg/ml ; 0.0000834 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.84
Solubility :	0.0405 mg/ml ; 0.000144 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-6.14
Solubility :	0.000205 mg/ml ; 0.000000728 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.16

Safety of [ 1313519-78-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1313519-78-6 ]

* 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 [ 1313519-78-6 ]

[ 1313519-78-6 ] Synthesis Path-Downstream 1~10

1
[ 1313519-78-6 ]
[ 2719001-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 24 h / 70 °C 2: palladium diacetate; XPhos / water; tetrahydrofuran / 18 h / 70 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - JP2021/155378, 2021, A

2
[ 1313519-78-6 ]
[ 2719001-67-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 24 h / 70 °C 2: palladium diacetate; XPhos / tetrahydrofuran / 18 h / 70 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - JP2021/155378, 2021, A

3
[ 1313519-78-6 ]
[ 2719001-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 24 h / 70 °C 2: XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / water; tetrahydrofuran / 23 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - JP2021/155378, 2021, A

4
[ 106-39-8 ]
[ 1313519-78-6 ]
[ 2118927-78-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; water at 70℃; for 24h;	1 Synthesis Example-1 2-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine(7.59 g, 27 mmol), 4-bromochlorobenzene (5. 32 g, 28 mmol), tetrakis (triphenylphosphine) palladium (470 mg, 0.41 mmol), and 2M-potassium phosphate aqueous solution (41 mL) were suspended in THF (54 mL) and stirred at 70 ° C. for 24 hours. After allowing to cool to room temperature, the reaction mixture was extracted with toluene. After drying over magnesium sulfate, it was distilled under reduced pressure. The obtained oily solid was purified by silica gel chromatography to obtain 2-phenyl-3- (4-chlorophenyl) pyridine, which is the target product of the white solid (yield 7.00 g, yield 98%).

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - JP2021/155378, 2021, A Location in patent: Paragraph 0104-0105

5
[ CAS Unavailable ]
[ 126866-35-1 ]
[ 1313519-78-6 ]
[ 298-06-6 ]
[ 2410989-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis-(triphenylphosphine)-palladium	S.13 Synthesis Example-13 Synthesis Example-13 Under nitrogen atmosphere, 3-bromo-5-chlorobiphenyl (50 g, 186.9 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-phenylpyridine (63 g, 224.3 mmol), and tetrakis(triphenylphosphine)palladium (4.3 g, 3.7 mmol) were suspended in THF (370 mL) at 60° C. A 4 M potassium phosphate (140 mL) was added to this suspension, and the mixture was heated under reflux for 10 h. After cooling to room temperature, toluene was added to the reaction mixture, and the organic layer was extracted. Magnesium sulfate and activated charcoal were added to the organic layer, and insoluble components were filtered off. The filtrate was concentrated, and then purified by recrystallization from ethanol to obtain the desired 3-chloro-5-(2-phenylpyridin-3-yl)biphenyl (5-1) (45.5 g, 71%). 1H-NMR (CDCl3): δ 8.73 (dd, 4.8, 1.7 Hz, 1H), 7.79 (dd, t. t, 1.7 Hz, 1H), 7.46 (t, 1.8 Hz, 1H), 7.42-7.30 (m, 9H), 7.27 (d, 1.8 Hz, 1H), 7.25-7.24 (m, 2H), 7.18 (t, 1.6 Hz, 1H).

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - US2022/274952, 2022, A1

6
[ 1313519-78-6 ]
[ 2588537-98-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ 2: palladium diacetate
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phosphate / tetrahydrofuran / 10 h / 60 °C / Reflux; Inert atmosphere 2: XPhos; potassium acetate; palladium diacetate / tetrahydrofuran / 6 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - US2022/274952, 2022, A1
[2]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - US2022/274952, 2022, A1

7
[ 1313519-78-6 ]
[ 2588537-90-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ 2: palladium diacetate 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phosphate / tetrahydrofuran / 10 h / 60 °C / Reflux; Inert atmosphere 2: XPhos; potassium acetate; palladium diacetate / tetrahydrofuran / 6 h / Inert atmosphere; Reflux 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phosphate / water / 6 h / Inert atmosphere; Reflux

8
[ 126866-35-1 ]
[ 1313519-78-6 ]
[ 2410989-70-5 ]

Yield	Reaction Conditions	Operation in experiment
71 %	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran at 60℃; Reflux; Inert atmosphere;	13 Synthesis Example-13 Under nitrogen atmosphere, 3-bromo-5-chlorobiphenyl (50 g, 186.9 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-phenylpyridine (63 g, 224.3 mmol), and tetrakis(triphenylphosphine)palladium (4.3 g, 3.7 mmol) were suspended in THF (370 mL) at 60° C. A 4 M potassium phosphate (140 mL) was added to this suspension, and the mixture was heated under reflux for 10 h. After cooling to room temperature, toluene was added to the reaction mixture, and the organic layer was extracted. Magnesium sulfate and activated charcoal were added to the organic layer, and insoluble components were filtered off. The filtrate was concentrated, and then purified by recrystallization from ethanol to obtain the desired 3-chloro-5-(2-phenylpyridin-3-yl)biphenyl (5-1) (45.5 g, 71%). (0115) 1H-NMR (CDCl3): δ 8.73 (dd, 4.8, 1.7 Hz, 1H), 7.79 (dd, t. t, 1.7 Hz, 1H), 7.46 (t, 1.8 Hz, 1H), 7.42-7.30 (m, 9H), 7.27 (d, 1.8 Hz, 1H), 7.25-7.24 (m, 2H), 7.18 (t, 1.6 Hz, 1H).

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - US2022/274952, 2022, A1 Location in patent: Paragraph 0113-0115

9
[ 1313519-78-6 ]
[ 2865886-45-7 ]
[ 2865886-32-2 ]

Yield	Reaction Conditions	Operation in experiment
92 %	With potassium phosphate; palladium diacetate; XPhos In tetrahydrofuran; water Inert atmosphere; Reflux;	2 Under an argon atmosphere, 2,4-bis(4-biphenylyl)-4-(5-chlorobiphenyl-3-yl)-pyrimidine (1.81 g, 3.17 mmol), 3-(4,4,5,5- Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-phenylpyridine (0.982 g, 3.49 mmol), 2M-potassium phosphate aqueous solution (4.8 mL), palladium acetate (14 mg, 0.063 mmol) ) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos, 61 mg, 0.127 mmol) were suspended in THF (32 mL) and refluxed for 15 h. After allowing to cool, water was added to the reaction mixture, the solid was collected by filtration, and washed with water and methanol to obtain 2-[5-(2-phenylpyridin-3-yl)-biphenyl-3-yl]-4, 6-bis(4-biphenylyl)pyrimidine (E2) was obtained (3.18 g, 92% yield).

Reference： [1]Current Patent Assignee: TOSOH CORPORATION - WO2022/244689, 2022, A1 Location in patent: Page/Page column 0119-0120

10
[ 1313519-78-6 ]
[ 2865886-43-5 ]
[ 2865886-30-0 ]

Yield	Reaction Conditions	Operation in experiment
99 %	With potassium phosphate; palladium diacetate; XPhos In tetrahydrofuran; water Inert atmosphere; Reflux;	1 Under an argon atmosphere, 4,6-bis(4-biphenylyl)-2-(5-chlorobiphenyl-3-yl)-pyrimidine (2.0 g, 3.5 mmol), 3-(4,4,5,5- Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-phenylpyridine (1.18 g, 4.2 mmol), 2M-potassium phosphate aqueous solution (6.3 mL), palladium acetate (15.7 mg, 0 .07 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos, 67 mg, 0.14 mmol) were suspended in THF (35 mL) and refluxed for 17 h. After allowing to cool, water was added to the reaction mixture, the solid was collected by filtration, and washed with water and methanol to obtain 2-[5-(2-phenylpyridin-3-yl)-biphenyl-3-yl]-4, 6-bis(4-biphenylyl)pyrimidine (E1) was obtained (yield 2.38 g, yield 99%)

Reference： [1]Current Patent Assignee: TOSOH CORPORATION - WO2022/244689, 2022, A1 Location in patent: Page/Page column 0117-0118

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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. 1313519-78-6 ] {[proInfo.proName]}

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[ 1313519-78-6 ] Synthesis Path-Downstream 1~10

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Organoboron

Aryls

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Pyridines

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[ 1313519-78-6 ]

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[ 1313519-78-6 ]