[ CAS No. 912844-88-3 ] {[proInfo.proName]}

Name: 912844-88-3|2-([1,1'-Biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|97%
Brand: Ambeed
SKU: A132927
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Quality Control of [ 912844-88-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 912844-88-3 ]

SDS Specification

Alternatived Products of [ 912844-88-3 ]

Product Details of [ 912844-88-3 ]

CAS No. :	912844-88-3	MDL No. :	MFCD18452169
Formula :	C₁₈H₂₁BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UUMDSELMDKINPL-UHFFFAOYSA-N
M.W :	280.17	Pubchem ID :	17942655
Synonyms :

Calculated chemistry of [ 912844-88-3 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	88.35
TPSA :	18.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-4.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	4.53
Log Po/w (WLOGP) :	3.65
Log Po/w (MLOGP) :	3.01
Log Po/w (SILICOS-IT) :	3.46
Consensus Log Po/w :	2.93

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.72
Solubility :	0.00532 mg/ml ; 0.000019 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.64
Solubility :	0.00642 mg/ml ; 0.0000229 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.51
Solubility :	0.0000866 mg/ml ; 0.000000309 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.22

Safety of [ 912844-88-3 ]

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 [ 912844-88-3 ]

* 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 [ 912844-88-3 ]
Downstream synthetic route of [ 912844-88-3 ]

[ 912844-88-3 ] Synthesis Path-Upstream 1~9

1
[ 2113-57-7 ]
[ 73183-34-3 ]
[ 912844-88-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 150℃; for 5 h; Inert atmosphere	Synthesis Example 8: Synthesis of Intermediate I-8 3-bromo-1,1′-biphenyl (20 g, 85.8 mmol) was dissolved in dimethylforamide (DMF) (1 L) under a nitrogen environment, bis(pinacolato)diboron (26 g, 103 mmol), (1,1′-bis(diphenylphosphine)ferrocene)dichloropalladium(II) (0.7 g, 0.85 mmol), and potassium acetate (58 g, 595 mmol) were added thereto, and the mixture was heated and refluxed at 150° C. for 5 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified through flash column chromatography to obtain Compound I-8 (20 g and 85percent). HRMS (70 eV, EI+): m/z calcd for C₁₈H₂₁BO₂: 280.1635. found: 280. Elemental Analysis: C, 77percent; H, 7percent

Reference： [1] Patent: US2017/331067, 2017, A1, . Location in patent: Paragraph 0212-0215

2
[ 2367-22-8 ]
[ 73183-34-3 ]
[ 912844-88-3 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 18, p. 5564 - 5568
[2] ACS Catalysis, 2017, vol. 7, # 7, p. 4535 - 4541

3
[ 2051-61-8 ]
[ 73183-34-3 ]
[ 912844-88-3 ]

Reference： [1] ACS Catalysis, 2017, vol. 7, # 5, p. 3199 - 3203

4
[ 73183-34-3 ]
[ 912844-88-3 ]

Reference： [1] Chemistry - A European Journal, 2016, vol. 22, # 47, p. 16787 - 16790

5
[ 594823-67-3 ]
[ 912844-88-3 ]

Reference： [1] Angewandte Chemie - International Edition, 2003, vol. 42, # 16, p. 1845 - 1848

6
[ 76-09-5 ]
[ 5122-95-2 ]
[ 912844-88-3 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 12, p. 3086 - 3089

7
[ 716-76-7 ]
[ 912844-88-3 ]

Reference： [1] Chemistry - A European Journal, 2016, vol. 22, # 47, p. 16787 - 16790

8
[ 92-52-4 ]
[ 25015-63-8 ]
[ 144432-80-4 ]
[ 912844-88-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 41, p. 10336 - 10340

9
[ 912844-88-3 ]
[ 1115023-84-1 ]

Reference： [1] Patent: KR2015/135070, 2015, A,

[ 912844-88-3 ] Synthesis Path-Downstream 1~38

1
[ 623-00-7 ]
[ 912844-88-3 ]
[ 64896-43-1 ]

Reference： [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 1845 - 1848

2
[ 594823-67-3 ]
6-tert-butyl-12-phenyl-5,6,7,12-tetrahydro-6-aza-12-bisma-dibenzo[a,d]cyclooctene [ No CAS ]
[ 912844-88-3 ]

Reference： [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 1845 - 1848

3
[ 862555-21-3 ]
[ 912844-88-3 ]
3-[5-biphenyl-3-yl-1-(4-chloro-benzyl)-3-methyl-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3352 - 3355

4
[ 1355363-66-4 ]
[ 912844-88-3 ]
[ 1355363-68-6 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 85℃; for 3h;Inert atmosphere;	Second Stage[0146] The following reagents and solvents were placed in a 200 itiL round-bottomed flask.Intermediate [15] : 2 g (3 mmol)[16] (biphenylboronic acid): 0.86 g (3 mmol)Pd(PPh)4 (tetrakis (triphenylphosphine) palladium(O) ) : 0.35 g (0.3 mmol)Toluene: 80 mLEthanol: 20 mL30 wt% Aqueous sodium carbonate solution: 30 mL[0147] The reaction solution was refluxed for 3 hours under heating and stirring in a nitrogen atmosphere. Upon completion of the reaction, water was added to the reaction solution, followed by stirring. Precipitated crystals were separated by filtration and washed with water, ethanol, and acetone to obtain a crude product. The crude product was dissolved in toluene under heating, subjected to hotfiltration, and recrystallized twice with a toluene solvent. The obtained crystals were vacuum dried at 100 C andpurified by sublimation at 10~4 Pa and 330C. As a result, 1.1 g (yield: 50%) of high-purity Example Compound B-9 was obtained .[ ALDI-TOF-MS]Observed value: m/z = 724.9Calculated value: 724.3The Ti energy of Example Compound B-9 measured as in Example 1 was 460 nm on a wavelength basis.[0148] The energy gap of Example Compound B-9 determined as in Example 1 was 3.6 eV.

Reference： [1]Patent: WO2012/8557,2012,A1 .Location in patent: Page/Page column 46-47

5
[ 1355363-71-1 ]
[ 912844-88-3 ]
[ 1355363-72-2 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 85℃; for 3h;Inert atmosphere;	Second Stage[0157] The following reagents and solvents were placed in a 200 mL round-bottomed flask.Intermediate [17] : 2 g (3 mmol)[16] (biphenylboronic acid): 0.86 g (3 mmol)Pd(PPh)4 (tetrakis (triphenylphosphine) palladium(O) ) : 0.35 g (0.3 mmol)Toluene: 80 mLEthanol: 20 mL30 wt% Aqueous sodium carbonate solution: 30 mL[0158] The reaction solution was refluxed for 3 hours under heating and stirring in a nitrogen atmosphere. Upon completion of the reaction, water was added to the reaction solution, followed by stirring. Precipitated crystals were separated by filtration and washed with water, ethanol, and acetone to obtain a crude product. The crude product was dissolved in toluene under heating, subjected to hotfiltration, and recrystallized twice with a toluene solvent. The obtained crystals were vacuum dried at 100 C andpurified by sublimation at 10"4 Pa and 340C. As a result, 0.84 g (yield: 38%) of high-purity Example Compound C-9 was obtained .[MALDI-TOF-MS]Observed value: m/z = 724.9Calculated value: 724.3The Ti energy of Example Compound C-9 measured as in Example 1 was 472 nm on a wavelength basis.[0159] The energy gap of Example Compound C-9 determined as in Example 1 was 3.2 eV.

Reference： [1]Patent: WO2012/8557,2012,A1 .Location in patent: Page/Page column 50-51

6
[ 912844-88-3 ]
potassium (trifluoromethyl)trimethoxyborate [ No CAS ]
[ 366-04-1 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 1577 - 1581

7
[ 58530-53-3 ]
[ 912844-88-3 ]
[ 1514914-36-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With palladium diacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; at 70℃; for 24h;Inert atmosphere;	General procedure: 2,4-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid pinacol ester (0.11 g, 0.55 mmol), KOH (56 mg, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (52 mg, 20 mol %) were dissolved in CH3CN (6 mL). The reaction was stirred at 70 C under nitrogen atmosphere for 24 h and then cooled. The solid was filtrated off and the filtrate was concentrated. The crude product was then dissolved in CH2Cl2 (10 mL) and the solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon evaporation, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give 3w (104 mg, 89%) as a colorless liquid.

Reference： [1]Tetrahedron,2013,vol. 69,p. 10996 - 11003

8
[ 1025506-08-4 ]
[ 912844-88-3 ]
[ 1613415-70-5 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3400 - 3403

9
[ 373-53-5 ]
[ 912844-88-3 ]
3-(fluoromethyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3086 - 3089

10
[ 76-09-5 ]
[ 5122-95-2 ]
[ 912844-88-3 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3086 - 3089

11
[ 92-52-4 ]
[ 25015-63-8 ]
[ 144432-80-4 ]
[ 912844-88-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 10336 - 10340
[2]Organometallics,2019

Yield	Reaction Conditions	Operation in experiment
88%	With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl tert-butyl ether; XPhos; In ethanol; at 20℃; for 0.5h;	General procedure: Method (1): Synthesis from 4-tert-butylchlorobenzene as a raw material: K3P04 · 7H20 (3.0 g, 8.85 mmol) and bis-pinacol borate (749 mg, 2.95 mmol) were sequentially added to the reaction flask.The catalyst-chloro (2-dicyclohexyl phosphino-2 ', 4', 6'-tri - triisopropyl-1,1'-biphenyl) (1,1'-biphenyl -2-amino-2'_ -yl)palladium(II) (12 mg, 0.015 mmol) and ligand 2-dicyclohexylphosphine-2',4',6/-triisopropylbiphenyl (4 mg, 0.008 mmol), followed by EtOH (6 mL) The mixture was stirred, and p-tert-butylchlorobenzene (0.5 mL, 2.95 mmol) was added and the mixture was reacted at room temperature for 0.5 h. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (2 mL) After washing with ethyl acetate (6 mL) in three portions, the filtrate was combined, and the solvent was evaporated to dryness, and the solvent was separated by silica gel (200 to 300 mesh). The eluent was petroleum ether and ethyl acetate. 10~80:1), obtained as a white solid, identified by NMR spectrum as 4-tert-butylphenylboronic acid pinacol ester, yield 98%
81%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90℃;	General procedure: Starting material bromobenzene (29.16 g, 185.72 mmol) was dissolved in DMF (930 ml) in a round bottom flask, and Bis(pinacolato)diboron (51.88 g, 204.29 mmol), Pd(dppf)Cl2 (4.55 g, 5.57 mmol), KOAc (54.68 g, 557.16 mmol) were added and stirred at 90 C. When the reaction is complete, the DMF is removed by distillation and extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 31.84 g of the product. (yield: 84%)
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In toluene; for 24h;	General procedure: Sub 2-1-3 (4.14g, 20mmol) was dissolved in toluene, bis-pinacolato diboron (5.58g, 22mmol), Pd(dppf)Cl2 catalyst (0.44g, 0.6mmol), KOAc (5.89g, 60mmol )was added. A borate compound was synthesized by stirring for 24 hours after the addition, as, after the thus obtained compound was separated over a silicagel column and recrystallized to obtain 3.8g of Sub 2 (3). (Yield: 75%)

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90 - 100℃;

General procedure: After the bromine compound (1 equivalent) was dissolved in DMF,Bis (pinacolato) diboron (1.1 eq.), Pd (dppf) Cl2 (0.03 mmol)After addition of KOAc (3 eq) And stirred at 90 to 100 C. When the reaction was complete, DMF was removed by distillation and extracted with CH2Cl2 and water.The organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to give product Sub2.

13
C₁₀H₄Cl₂N₂O [ No CAS ]
[ 912844-88-3 ]
C₂₃H₁₆N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; for 24h;Inert atmosphere; Reflux;	500 mL round bottom flask on an intermediate E-4 15.0 g (62.8 mmol), Intermediate e-86-1 17.6 g (62.8 mmol), potassium carbonate 21.7 g(156.9 mmol), tetrakis (triphenylphosphine) palladium (0), 3.6 g (3.1 mmol) and 1,4-dioxane 200 mL, to 100 mL of waterAfter semi-put, and heated to reflux for 24 hours under a nitrogen stream. The mixture obtained therefrom in 600 mL of methanolAfter filtration the crystallized solid was added, filtered through a silica gel / celite and dissolved in monochlorobenzene, and the organic solvent enemyAfter removal equivalents, it was recrystallized with methanol to afford the intermediate e-86-2 (15.7 g, yield 70%).

Reference： [1]Patent: KR2015/84657,2015,A .Location in patent: Paragraph 1549-1552

14
[ 912844-88-3 ]
C₃₀H₂₁Cl [ No CAS ]