2920-38-9|[1,1'-Biphenyl]-4-carbonitrile| Ambeed

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Structure of 2920-38-9

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Quality Control of [ 2920-38-9 ] Purity: 98% SDS Specification

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Product Citations

Versatile Nanoporous Organic Polymer Catalyst for the Size- Selective Suzuki-Miyaura Coupling Reaction

Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon ; Swager, Timothy M. ;

DOI: 10.1021/acsanm.2c04393 ACS Appl. Nano Mater.,2022,5(12):18603-18611.

Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki−Miyaura coupling reaction ; size-selective reaction ; catalyst processing

Purchased from AmBeed: 128796-39-4 ; 10365-98-7 ; 98-80-6 ; 556-96-7 ; 171663-13-1 ; 71597-85-8 ; 402-43-7 ; 2042-37-7 ; 22385-77-9 ; 16419-60-6 ; 15862-18-7 ; 87199-15-3 ; 171408-84-7 ; 643-58-3 ; 591-50-4 ; 76911-73-4 ; 398-36-7 ; 14871-92-2 ; 5720-07-0 ; 945976-76-1 ; 366-18-7 ; 2920-38-9 ; 623-00-7 ; 24973-49-7 ; 588-59-0 ; 128796-39-4 ; 5723-93-3 ; 17057-88-4 ; 126485-55-0

Product Details of [ 2920-38-9 ]

CAS No. :	2920-38-9
Formula :	C₁₃H₉N
M.W :	179.22
SMILES Code :	N#CC1=CC=C(C2=CC=CC=C2)C=C1
MDL No. :	MFCD00001821
InChI Key :	BPMBNLJJRKCCRT-UHFFFAOYSA-N
Pubchem ID :	18021

Safety of [ 2920-38-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302+H312-H331
Precautionary Statements:	P261-P302+P352
Class:	6.1
UN#:	3439
Packing Group:	Ⅲ

Computational Chemistry of [ 2920-38-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	56.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	23.79 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.22
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.26
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.23
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.0
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.54
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.05

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.57
Solubility	0.0479 mg/ml ; 0.000267 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.43
Solubility	0.066 mg/ml ; 0.000368 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.0
Solubility	0.0018 mg/ml ; 0.00001 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.08 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.81

Application In Synthesis of [ 2920-38-9 ]

* 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 [ 2920-38-9 ]

[ 2920-38-9 ] Synthesis Path-Downstream 1~19

1
[ 42464-09-5 ]
[ 100-47-0 ]
[ 100-02-7 ]
[ 24973-50-0 ]
[ 24973-49-7 ]
[ 2920-38-9 ]

References: [1]Journal of the American Chemical Society,1981,vol. 103,p. 4558 - 4565.

2
[ 42464-09-5 ]
[ 100-47-0 ]
[ 24973-50-0 ]
[ 24973-49-7 ]
[ 2920-38-9 ]
[ 65-85-0 ]

References: [1]Journal of the American Chemical Society,1981,vol. 103,p. 4558 - 4565.

3
[ 369-57-3 ]
[ 100-47-0 ]
[ 24973-50-0 ]
[ 24973-49-7 ]
[ 2920-38-9 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 1594 - 1603.

4
[ 100-47-0 ]
[ 108-95-2 ]
[ 24973-50-0 ]
[ 24973-49-7 ]
[ 2920-38-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1987,p. 1167 - 1174.

5
[ 100-47-0 ]
[ 94-36-0 ]
[ 24973-50-0 ]
[ 24973-49-7 ]
[ 2920-38-9 ]
[ 65-85-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1981,p. 1109 - 1120.

6
[ 623-03-0 ]
argon [ No CAS ]
[ 224311-51-7 ]
[ 98-80-6 ]
[ 2920-38-9 ]

Yield	Reaction Conditions	Operation in experiment
159 mg (89%)	With potassium fluoride;palladium diacetate; In tetrahydrofuran;	EXAMPLE 32 Synthesis of 4-cyanobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-chlorobenzonitrile (136 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 ml), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 159 mg (89percent) of the title compound.
159 mg (89%)	With potassium fluoride;palladium diacetate; In tetrahydrofuran;	Example 32 Synthesis of 4-cyanobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-chlorobenzonitrile (136 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 159 mg (89percent) of the title compound.

References: [1]Patent: US6307087,2001,B1 .
[2]Patent: US2004/171833,2004,A1 .

7
[ 1293-65-8 ]
[ 2920-38-9 ]
[ 263261-10-5 ]

References: [1]Organometallics,2000,vol. 19,p. 1096 - 1106.

8
[ 57774-35-3 ]
[ 2920-38-9 ]

References: [1]Journal of Chemical Research,2012,vol. 36,p. 407 - 410.

9
potassiumhexacyanoferrate(II) trihydrate [ No CAS ]
[ 2974-92-7 ]
[ 92-52-4 ]
[ 2051-61-8 ]
[ 24973-50-0 ]
[ 2920-38-9 ]
[ 4128-63-6 ]
[ 2051-62-9 ]

References: [1]Russian Chemical Bulletin,2012,vol. 61,p. 980 - 983.
Izv. Akad. Nauk, Ser. Khim.,2012,p. 974 - 978,5.

10
[ 108-86-1 ]
[ 100-47-0 ]
[ 24973-50-0 ]
[ 24973-49-7 ]
[ 2920-38-9 ]

References: [1]ACS Catalysis,2017,vol. 7,p. 3336 - 3343.

11
[ 3058-39-7 ]
[ 865-47-4 ]
[ 71-43-2 ]
[ 2920-38-9 ]
[ 185259-36-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	With N,N'-diethylurea; at 120℃; for 24h;Schlenk technique; Sealed tube; Inert atmosphere;	General procedure: Aryl iodides (0.2 mmol) t-BuOK (0.6 mmol, 3.0 equiv), and U6 (0.02 mmol, 10 mol%) were added in dried Schlenk tubes. Benzene (2 mL) were added into tubes by syringe. The septum-sealed tube was evacuated and refilled with nitrogen three times. The mixture was stirred under a nitrogen atmosphere in sealed Schlenk tubes at 120 C for 24 h. The reaction was cooled down to room temperature. The mixture was filtered through a short plug of silica gel, washed with a copious amount of ethyl acetate. The combined organic phase was concentrated under vacuum. The product was purified through flash column chromatography on 300-400 mesh silica gel with hexane/ethyl acetate as eluent. Solvent was removed under vacuum to give the pure product.

References: [1]Catalysis Communications,2018,vol. 111,p. 95 - 99.

12
[ 109-69-3 ]
[ 2920-38-9 ]
[ 74-88-4 ]
[ 37909-95-8 ]
4-butyl-4-phenylcyclohexa-2,5-dienone [ No CAS ]
trans-4-butyl-1-methyl-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
cis-4-butyl-1-methyl-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]