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Structure of 122775-35-3

Chemical Structure| 122775-35-3

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James Nyakuchena ;

Abstract: Metal organic frameworks (MOFs) are a class of highly porous crystalline materials constructed from metal nodes connected by multitopic organic ligands. Due to their unique properties such as large surface area, tunable pore structure, and structural diversity, they have demonstrated potential in a wide array of applications including gas storage and separation, sensing, catalysis, and drug delivery. However, there are only a handful of MOFs reported that have electrical conductivity, which prevents their applications in photoelectronic and photocatalytic applications. This is because hard metals and redox inactive ligands with terminal hard linking bases such as carboxylates are often used in constructing these materials. In addition, the porous nature of these materials leaves voids between the polymeric chains, which cuts off communication between the densely packed units. It was not until recently that MOFs with charge conductivity were reported after replacing the hard-linking nodes with soft acid/base counterparts. However, the charge transport mechanism that is responsible for their conductivity remains poorly understood. The objective of my research projects is to have a fundamental understanding of charge transport mechanisms in MOFs to facilitate their applications in photo-electronics and photocatalysis. In this report, I will discuss fundamental insights into charge transport mechanisms in 2D M-THQ MOFs (M= Cu, Fe, Ni, and Zn) (chapters 3 and 4) and 1D pyrene-tetra thiol-based nanosheets (chapter 6). Chapter 3 focuses on the experimental evidence of through bond charge transport in Cu-THQ semiconductive MOF through a combination of spectroscopic techniques and DFT calculation. Chapter 4 reports the dependence of exciton dynamics and band structure engineering on metal nodes in M-THQ MOF (M= Fe, Ni, and Zn). Chapter 5 discusses the impact of Ligand size in 2D MOFs on photoconduction and charge transport mechanisms. In Chapter 6 I discuss the design and synthesis of 1D pyrene-tetra thiol-based MOFs, and the impact of pi-pi stacking on photoconduction. I also synthesized a new sulfur-decorated MOF for potential application in metal ion batteries and white light emissive COFs which will be discussed in chapters 7 and 8. Finally, chapter 9 outlines the future directions of this project.

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Alternative Products

Product Details of [ 122775-35-3 ]

CAS No. :122775-35-3
Formula : C8H11BO4
M.W : 181.98
SMILES Code : OB(C1=CC=C(OC)C(OC)=C1)O
MDL No. :MFCD01074574
InChI Key :RCVDPBFUMYUKPB-UHFFFAOYSA-N
Pubchem ID :2734702

Safety of [ 122775-35-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 122775-35-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 49.25
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

58.92 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.77
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.62
Log Po/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.

-0.25
Log Po/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

-0.74
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.17

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.6
Solubility 4.6 mg/ml ; 0.0253 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.59
Solubility 4.7 mg/ml ; 0.0258 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-1.54
Solubility 5.21 mg/ml ; 0.0286 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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

No
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

No
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

No
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.

-6.86 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

1.0
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

1.0 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)

2.2

Application In Synthesis of [ 122775-35-3 ]

* 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.

  • Downstream synthetic route of [ 122775-35-3 ]

[ 122775-35-3 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 122775-35-3 ]
  • [ 425392-44-5 ]
  • 5-chloro-2-(3,4-dimethoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester [ No CAS ]
  • 2
  • [ 53595-65-6 ]
  • [ 122775-35-3 ]
  • [ 959144-38-8 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 100℃;Inert atmosphere; Sealed tube; Preparative Example 24PREPARATION OF 5-(3,4-DIMETHOXYPHENYL)THIOPHENE-2-SULFONAMIDEA stirred solution of 5-bromothiophene-2-sulfonamide (2 g, 8.26 mmol) and (3,4-dimethoxyphenyl)boronic acid (1.8 g, 9.90 mmol) in 30 mL DMF at room temperature was purged with N2 gas for 10 mins. To this stirred solution was added (Ph3P)4Pd (1.9 g, 1.65 mmol) and saturated Na2CO3/H2O (2.63 g, 3 mmol). The N2 purge was stopped and the reaction mixture was sealed and heated with a preheated oil bath at 100 C. overnight. The reaction mixture was filtered and the filtrate was partitioned between saturated NaHCO3 and EtOAc, the layers were separated, and the aqueous layer was extracted again with EtOAc. The combined organic layers were dried (MgSO4), filtered, and evaporated in vacuo. The resulting material was purified by silica gel chromatography (40% EtOAc in hexane) to provide the product, as a light yellow solid.1H NMR (500 MHz, CD3OD) δ (ppm): 7.56 (d, 1H), 7.30 (d, 1H), 7.24 (m, 2H), 7.00 (d, 1H), 3.90 (d, 6H).
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 20 - 100℃;Sealed tube; PREPARATIVE EXAMPLE 10 PREPARATION OF 5-(3,4-DIMETHOXYPHENYL)THTOPHENE-2-SULFON AMIDEA stirred solution of 5-bromothiophene-2-suIfonamide (2 g, 8.26 mmol) and (3,4- dimethoxyphenyl)boronic acid (1.8 g, 9.90 mmol) in 30 mL DMF at room temperature was purged with N2 gas for 10 mins. To this stirred solution was added (Ph3P)4Pd (1.9 g, 1.65 mmol) and saturated Na2CO3/H2θ (2.63 g, 3 mmol). The N2 purge was stopped and the reaction mixture was sealed and heated with a preheated oil bath at 1000C overnight. The reaction mixture was filtered and the filtrate was partitioned between saturated NaHCO3 and EtOAc, the layers were separated, and the aqueous layer was extracted again with EtOAc. The combined organic layers were dried (MgSO^), filtered, and evaporated in vacuo. The resulting material was purified by silica gel chromatography (40% EtOAc in hexane) to provide the product, as a light yellow solid.1H NMR (500 MHz, CD3OD) δ (ppm): 7.56 (d, IH), 7.30 (d, IH), 7.24 (m, 2H), 7.00 (d, IH), 3.90 (d,SH).
  • 3
  • [ 122775-35-3 ]
  • [ 120157-97-3 ]
  • [ 708269-37-8 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 20 - 85℃; for 24.0833h; To a solution of 4-BROMOPHENETHYLAMINE (10G, 48. 98mmol) in anhydrous DMF (150mL), containing anhydrous triethylamine (35mL, 244.9 mol), was added BOC2O. The reaction mixture was heated for 15 minutes at 50C. After cooling to room temperature, brine (100ML) and HCI (1N, 100ML) were added subsequently, and the mixture was extracted several times with ether. The recombined organic layer was washed again with brine, dried over sodium sulfate, filtered and evaporated. The crude was flashed with 10% ethyl acetate in hexanes to give the [2- (4-BROMO-PHENYL)-ETHYL]-CARBAMIC acid tert-butyl ester.'H NMR (CDCI3, 300MHZ) : 1.41 (s, 9H); 2.22 (t, J=7. 1HZ, 2H); 3.31 (m, 2H); 4.67 (s, broad, 1 H); 7.03 (d, J=8.2Hz, 2H); 7.38 (d, J=8.2Hz, 2H). A mixture of the above mentioned compound (1. 00g, 3. 33MMOL), 3, 4-DIMETHOXYPHENYLBORONIC acid (1. 21 G, 6. 66MMOL), and potassium hydroxide (2N, 5mL, 10MMOL) in THF (15mL) was degassed using argon for 5 minutes. Palladium tetrakis-triphenylphosphine (200mg, 0. 167MMOL) was added and the mixture was heated at 85C. After 24 hours, the reaction mixture was allowed to cool to room temperature. Brine (20mL) was added and the reaction mixture was extracted several times with ether. The recombined organic phase was extracted with brine, dried over sodium sulfate, filtered, and evaporated. Silica gel chromatography of the crude using 20% ethyl acetate/n-hexane afforded [2- (3', 4'-DIMETHOXY-BIPHENYL-4YL)-ETHYLAMINE]-CARBAMIC acid tert-butyl ester as a white SOLID. 1H-NMR (CDCI3, 300MHZ) : 1.44 (s, 9H); 2.82 (t, J=6.9Hz, 2H); 3.39 (m, 2H); 3.91 (s, 3H); 3.93 (s, 3H); 4.67 (s, broad, 1H) ; 6.92 (d, J=8.2Hz, 1 H) ; 7.11 (m, 2H); 7.25 (m, 2H); 7.48 (d, J=8. 1 Hz, 2H). A solution of the above mentioned compound (1.14g, 3. 19mmol) in anhydrous methanol (50mL) was cooled in ice bath and then treated drop wise with acetyl chloride. Stirring was continued for 30 minutes at the same temperature followed by overnight stirring at room temperature. About 30mL of the solvent was removed by evaporation and the mixture was diluted with 200mL of ether. The entitled product was collected as a white solid by filtration, followed by washing with anhydrous ether and drying under high VACUUM.'H-NMR (D20, 300MHZ) : 2.80 (t, J=6.9Hz, 2H); 3.40 (m, 2H); 3.91 (s, 3H); 3.93 (s, 3H); 4.77 (s, broad, 1H) ; 7.00 (d, J=8.2Hz, 1H) ; 7.15 (m, 2H); 7.26 (m, 2H); 7.50 (d, J=8. 1HZ, 2H)
  • 4
  • [ 122775-35-3 ]
  • [ 171178-33-9 ]
  • [ 897359-55-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 3h;Heating / reflux;Product distribution / selectivity; Method A: To a solution of 6-chloro-pyrido[3,2-d]pyrimidin-4(3H)-one (200 mg,1.1 mmol) in 1 ,4-dioxane (20 ml) and water (10 ml) was added 3,4-dimethoxyphenyl boronic acid (240 mg, 1.32 mmol), potassium carbonate (380 mg, 2.75 mmol) and tetrakis(triphenylphosphine)palladium(0) (63 mg, 0.055 mmol). The reaction mixture was refluxed for 3 hours, cooled down to room temperature and the solvents were evaporated in vacuo. The residue was adsorbed on silica, purified by silica gel column chromatography (the mobile phase being a acetone/dichloromethane mixture, in a ratio gradually ranging from 30:70 to 40:60) and characterised by its mass spectrum as follows : MS (m/z) : 284 ([M+H]+, 100).Method B: A suspension of 2-carboxamido-3-amino-6-(3,4-dimethoxyphenyl)- pyridine (770 mg, 2.8 mmol) in triethyl orthoformate (28 ml) was refluxed for 12 hours. Then, the reaction mixture was cooled down and evaporated to dryness. The residue was purified by silica gel column chromatography (the mobile phase being an ethyl acetate/hexane mixture in a ratio gradually ranging from 2:8 to 3:7), resulting in the pure title compound (530 mg, yield 67 %) which was characterised by its mass spectrum as follows: MS (m/z) : 284 ([M+H)+, 100].
  • 5
  • [ 132131-24-9 ]
  • [ 122775-35-3 ]
  • [ 934426-28-5 ]
YieldReaction ConditionsOperation in experiment
44% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 16h; Example 3: Preparation of [6-(3,4-Dimethoxy-phenyI)-quinazolin-4-yI]-(4- morpholin-4-yl-phenyI)-ammeStep 1: 4-Amino-3',4'-dimethoxy-biphenyl-3-carbonitrileA mixture of 3,4-dimethoxyboronic acid (956mg, 2eq), intermediate 1 ( 640mg, leq), tetrakis (triphenylphosphine) palladium (0) (10%, 303mg) in DME / 2M aq sodium carbonate ( 2:1, 21ml) was heated to 80 for 16h.The cooled reaction mixture was diluted with ethyl acetate and washed with further aq sodium carbonate then water. The dried organic phase was concentrated to a dark red gum which was dissolved in CH2Cl2 and loaded onto a SPE cartridge ( Si5 2Og) and eluted with CH2Cl2. The major fractions containing product were combined and concentrated to a semi-solid which was triturated with diethyl ether and the desired compound isolated by filtration as a light brown solid (296mg5 44%) EPO <DP n="20"/>LC-MS rt 2.73 no ion observed1H (DMSO) 57.77 (IH, s), 7.71 (IH, d), 7.2 (IH5 s), 7.17 (IH5 d), 7.03 (IH, d), 6.91(IH5 d). 6.17 (2H5 br s), 3.89 (3H5 s), 3.83 (3H5 s)
  • 6
  • [ 122775-35-3 ]
  • [ 145543-82-4 ]
  • [ 1067911-49-2 ]
  • 7
  • [ 518057-72-2 ]
  • [ 122775-35-3 ]
  • [ 298-12-4 ]
  • [ 960231-96-3 ]
YieldReaction ConditionsOperation in experiment
46% With N,N-dimethyl-formamide; In acetonitrile; at 100℃; for 0.333333h;Microwave irradiation; A mixture of <strong>[518057-72-2]3-amino-6-fluorobenzamide</strong> (85 mg, 0.5 mmol), 3,4-dimethoxyphenylboronic acid (91 mg, 0.5 mmol) and glyoxylic acid monohydrate (46 mg, 0.5 mmol) in acetonitrile (2.0 mL) and DMF (0.2 mL) was heated at 100 C. for 20 min. in a microwave reactor. After removal of solvent, the crude was triturated with methylene chloride. The precipitate formed was collected by filtration and washed with methylene chloride to give 13A after drying, yield: 46%. 1H NMR (400 MHz, Methanol-d4) delta ppm 3.81 (s, 3H) 3.82 (s, 3H) 4.92 (s, 1H) 6.83-6.89 (m, 1H) 6.93 (d, J=8.35 Hz, 1H) 6.96-7.02 (m, 1H) 7.03-7.07 (m, 1H) 7.10 (d, J=1.76 Hz, 1H) 7.15 (dd, J=5.93, 2.86 Hz, 1H), LCMS: 349 (M+1).
  • 8
  • [ 50670-58-1 ]
  • [ 122775-35-3 ]
  • [ 1370618-99-7 ]
YieldReaction ConditionsOperation in experiment
78% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In methanol; water; toluene;Inert atmosphere; Reflux; General procedure: To a solution of bromobiphenylaldehyde (6, 260 mg, 1 mmol) and various phenyl boronic acids (7a-j, 1 mmol) in 2 M aqueous sodium carbonate (2 mL) and toluene/ethanol (9:3 mL) is added a catalytic amount (0.4% mol) of tetrakis-triphenylphosphine palladium, and the mixture was reflux under argon atmosphere for 2-3 h. After completion of reaction, the suspension is cooled and extracted with ethyl acetate (3 × 30 mL) and the organic phase was washed with water and brine, dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to get the crude product. This residue was further purified by column chromatography using ethyl acetate and hexane to afford the pure terphenylaldehydes (8).
  • 9
  • [ 3141-24-0 ]
  • [ 1394840-81-3 ]
  • [ 122775-35-3 ]
  • [ 1394840-82-4 ]
YieldReaction ConditionsOperation in experiment
20% In ethyl acetate; Example 5 Synthesis of SA-59, SA-60 and SA-61 3-bromo-2,5-bis(3',4'-dimethoxyphenyl)thiophene (18) was prepared by the reaction of <strong>[3141-24-0]2,3,5-tribromothiophene</strong> (17) (321 mg, 1 mmol) and (3,4-dimethoxyphenyl)boronic acid (15) (419 mg, 2.3 mmol) according to the similar procedure for compound 16. The reaction mixture was purified by column chromatography (10%-30% EtOAc in hexanes) and afforded 18 (337 mg, 77% yield) as a yellow solid. SA-60 was also isolated (97 mg, 20% yield) from the reaction above as a dark yellow solid.
  • 10
  • [ 3141-24-0 ]
  • [ 1394840-81-3 ]
  • [ 122775-35-3 ]
  • [ 1394840-83-5 ]
YieldReaction ConditionsOperation in experiment
65% In ethyl acetate; Example 6 Synthesis of SA-62 Compound 19 was prepared by the reaction of 2,5-dibromothiophene (17) (1.14 g, 5.24 mmol) and (3,4-dimethoxyphenyl)boronic acid (15) (910 mg, 5 mmol) according to the similar procedure for compound 16. The reaction mixture was purified by flash column chromatography (FCC) (5%-20% EtOAc in hexanes) and afforded compound 19 (509 mg, 34% yield) as a yellowish crystal. Compound 16 was also isolated (578 mg, 65% yield) as a yellow solid.
  • 11
  • [ 122775-35-3 ]
  • [ 57103-20-5 ]
  • 3,6-bis(3,4-dimethoxyphenyl)-9-phenylcarbazole [ No CAS ]
  • 12
  • [ 122775-35-3 ]
  • [ 56844-40-7 ]
  • [ 1428537-30-7 ]
  • 14
  • [ 1813-33-8 ]
  • [ 122775-35-3 ]
  • [ 935520-49-3 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; toluene; for 12h;Reflux; General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).
  • 15
  • [ 3682-14-2 ]
  • [ 122775-35-3 ]
  • [ 298-12-4 ]
  • [ 960232-00-2 ]
  • 16
  • [ 3682-14-2 ]
  • [ 122775-35-3 ]
  • methyl 3-(1-(2-(3,4-dimethoxyphenyl)-2-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-6-ylamino)acetyl)pyrrolidin-2-yl)-4-(isopropylsulfonyl)phenylcarbamate [ No CAS ]
  • 17
  • [ 53848-17-2 ]
  • [ 122775-35-3 ]
  • C15H17NO2 [ No CAS ]
  • 18
  • [ 1123-63-3 ]
  • [ 122775-35-3 ]
  • 3',4'-dimethoxy-2,6-dimethyl-[1,1'-biphenyl]-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; at 75℃;Inert atmosphere; General procedure: In 25 mL round bottom flask equipped with reflux condenser, 0.0004 mol of 4-chloro-3,5-dimethylphenol mixed with appropriate quantity of arylboronic acid (1-6) and 0.05 g of Pd(PPh3)4 were added into the flask containing 20 mL of absolute ethanol under inert atmospheric condition (N2) gas. The mixture was stirred and heated and 5 mL of solution (5% Na2CO3) were added into the flask.The reaction mixture was stirred and heated at 75 C for 5-6 h then followed by TLC and monitor reactions using (n-hexane and ethyl acetate) in 2:3 ratio v/v. The mixture was filtrated off to remove the inorganic salt and the residue of pallidum catalyst, washed by cooled ethanol and the solvent was removed and decanted by cooled ether (Scheme-I).
  • 19
  • [ 13338-63-1 ]
  • [ 122775-35-3 ]
  • [ 80235-72-9 ]
YieldReaction ConditionsOperation in experiment
79% With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid; In tetrahydrofuran; water; at 80℃; for 2h;Inert atmosphere; Schlenk technique; General procedure: Under a nitrogen atmosphere, aryl acetonitrile 1 (3mmol), arylboronic acids 2 (6mmol), palladium acetate (5mol %), 2,2′-Bipyridine (10mol %), trifluoroacetic acid (30mmol), potassium fluoride (6mmol), tetrahydrofuran (20mL), and water (10mL) were successively added to a Schlenk reaction tube. The reaction mixture was stirred vigorously at 80C for 2h. After the reaction mixture was cooled to room temperature, saturated sodium bicarbonate (30mL) was added into the solution, and the mixture was extracted with ethyl acetate (10mL) for 3 times. The combined organic layer was concentrated in vacuo. The residue was purified by flash column chromatography to afford desired product 3.
 

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Related Functional Groups of
[ 122775-35-3 ]

Organoborons

Chemical Structure| 182344-21-4

A183790 [182344-21-4]

(4-Hydroxy-3-methoxyphenyl)boronic acid

Similarity: 1.00

Chemical Structure| 164014-95-3

A656685 [164014-95-3]

1,4-Benzodioxane-6-boronic acid

Similarity: 0.94

Chemical Structure| 192182-54-0

A154620 [192182-54-0]

3,5-Dimethoxybenzeneboronic acid

Similarity: 0.94

Chemical Structure| 5720-07-0

A376270 [5720-07-0]

4-Methoxyphenylboronic acid

Similarity: 0.94

Chemical Structure| 265664-52-6

A920211 [265664-52-6]

(4-(2-Methoxyethoxy)phenyl)boronic acid

Similarity: 0.92

Aryls

Chemical Structure| 182344-21-4

A183790 [182344-21-4]

(4-Hydroxy-3-methoxyphenyl)boronic acid

Similarity: 1.00

Chemical Structure| 192182-54-0

A154620 [192182-54-0]

3,5-Dimethoxybenzeneboronic acid

Similarity: 0.94

Chemical Structure| 5720-07-0

A376270 [5720-07-0]

4-Methoxyphenylboronic acid

Similarity: 0.94

Chemical Structure| 265664-52-6

A920211 [265664-52-6]

(4-(2-Methoxyethoxy)phenyl)boronic acid

Similarity: 0.92

Chemical Structure| 279262-15-6

A373897 [279262-15-6]

(4-(2-Ethoxyethoxy)phenyl)boronic acid

Similarity: 0.92

Ethers

Chemical Structure| 182344-21-4

A183790 [182344-21-4]

(4-Hydroxy-3-methoxyphenyl)boronic acid

Similarity: 1.00

Chemical Structure| 192182-54-0

A154620 [192182-54-0]

3,5-Dimethoxybenzeneboronic acid

Similarity: 0.94

Chemical Structure| 5720-07-0

A376270 [5720-07-0]

4-Methoxyphenylboronic acid

Similarity: 0.94

Chemical Structure| 265664-52-6

A920211 [265664-52-6]

(4-(2-Methoxyethoxy)phenyl)boronic acid

Similarity: 0.92

Chemical Structure| 279262-15-6

A373897 [279262-15-6]

(4-(2-Ethoxyethoxy)phenyl)boronic acid

Similarity: 0.92