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6301-56-0 Usage

General Description

Biphenyl-3-Carboxylic Acid Ethyl Ester is a synthetic, organic chemical compound that belongs to the class of biphenyls and derivatives. As an ester, it is formed by condensation of an alcohol (ethyl alcohol in this case) and an acid (biphenyl-3-carboxylic acid). The chemical is known for its stability and is characterized by the biphenyl structure in its composition, which often contributes to a variety of physical and chemical properties including high melting and boiling points. Biphenyl-3-Carboxylic Acid Ethyl Ester does not occur naturally and is used in various industries, although information about its specific applications is somewhat sparse. However, like other biphenyl derivatives, it may have uses in pharmaceuticals, agrochemicals, and materials science.

Check Digit Verification of cas no

The CAS Registry Mumber 6301-56-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,3,0 and 1 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 6301-56:
(6*6)+(5*3)+(4*0)+(3*1)+(2*5)+(1*6)=70
70 % 10 = 0
So 6301-56-0 is a valid CAS Registry Number.
InChI:InChI=1/C15H14O2/c1-2-17-15(16)14-10-6-9-13(11-14)12-7-4-3-5-8-12/h3-11H,2H2,1H3

6301-56-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name BIPHENYL-3-CARBOXYLIC ACID ETHYL ESTER

1.2 Other means of identification

Product number -
Other names 3-Phenylbenzoic acid ethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6301-56-0 SDS

6301-56-0Synthetic route

Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With potassium carbonate; Pd(OAc)2 on N,N-diethylaminopropylated alumina In ethanol; water at 20℃; for 4h; Suzuki-Miyaura coupling;100%
With sodium carbonate; palladium on activated charcoal In ethanol at 20℃; for 3h; Suzuki-Miyaura cross-coupling;99%
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 6h; Suzuki-Miyaura coupling reaction;99%
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

phenylmanganese(II) chloride
71478-47-2

phenylmanganese(II) chloride

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; 1,2-dimethoxyethane at 0 - 20℃; for 0.5h;99%
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

4-iodo-biphenyl
1591-31-7

4-iodo-biphenyl

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With triethylamine; dichloro bis(acetonitrile) palladium(II) at 70℃; for 24h;99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; [(Ph2CH=NOH)PdCl]2 In benzene at 120℃; for 3h;90%
ethyl 4-(tosyloxy)benzoate
98634-20-9

ethyl 4-(tosyloxy)benzoate

potassium phenyltrifluoborate

potassium phenyltrifluoborate

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With triethylamine; palladium diacetate In ethanol at 80℃; Suzuki-Miyaura cross-coupling;99%
[2-(hydroxymethyl)phenyl](diisopropyl)phenylsilane
913621-71-3

[2-(hydroxymethyl)phenyl](diisopropyl)phenylsilane

ethyl 4-chlorobenzoate
7335-27-5

ethyl 4-chlorobenzoate

A

1,1-diisopropyl-1,3-dihydrobenzo[c][1,2]oxasilole
913621-73-5

1,1-diisopropyl-1,3-dihydrobenzo[c][1,2]oxasilole

B

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With potassium carbonate; copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); ruphos In tetrahydrofuran; N,N-dimethyl-formamide at 75℃; for 15h; Product distribution / selectivity;A 95%
B 99%
With copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; ruphos In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 15h; Inert atmosphere;A > 95 %Chromat.
B 96%
p-(ethoxycarbonyl)phenyl triflate
125261-30-5

p-(ethoxycarbonyl)phenyl triflate

potassium phenyltrifluoborate

potassium phenyltrifluoborate

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; cesium acetate In tetrahydrofuran Stille coupling; Reflux; Inert atmosphere;99%
bromobenzene
108-86-1

bromobenzene

4-iodobenzoic acid ethyl ester
51934-41-9

4-iodobenzoic acid ethyl ester

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Negishi coupling reaction; Inert atmosphere;
Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78 - 20℃; Negishi coupling reaction; Inert atmosphere;
Stage #3: 4-iodobenzoic acid ethyl ester With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; hexane at 60℃; for 2h; Negishi coupling reaction; Inert atmosphere;
99%
Stage #1: bromobenzene With indium; bathophenanthroline; 3-chloroprop-1-ene; lithium chloride; cobalt(II) bromide In tetrahydrofuran at 100℃; for 23h; Inert atmosphere;
Stage #2: 4-iodobenzoic acid ethyl ester With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran at 80℃; for 21h; Inert atmosphere;
95%
ethyl 4-(tosyloxy)benzoate
98634-20-9

ethyl 4-(tosyloxy)benzoate

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); potassium carbonate; triphenylphosphine In toluene at 100℃; for 5h; Suzuki coupling; Inert atmosphere;99%
With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine tetrafluoroborate; potassium carbonate In water; toluene at 20℃; for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere;99%
With potassium phosphate; (NC5H3(N2C7H4(CH2)3CH3)2)NiBr(1+)*Br(1-)=Ni(NC5H3(N2C7H4(CH2)3CH3)2)Br2; triphenylphosphine In 1,4-dioxane at 100℃; for 24h; Suzuki-Miyaura coupling;98%
With 1,1'-bis-(diphenylphosphino)ferrocene; (9-phenanthrenyl)Ni(II)(PPh3)2Cl; potassium carbonate In toluene at 110℃; for 20h; Suzuki Coupling; Inert atmosphere;87%
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

tetraphenyltin(IV)
595-90-4

tetraphenyltin(IV)

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With palladium 10% on activated carbon; lithium chloride In 1-methyl-pyrrolidin-2-one at 90℃; for 24h; Stille coupling;99%
ethyl 4-(methanesulfonyloxy)benzoate
902148-89-4

ethyl 4-(methanesulfonyloxy)benzoate

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine tetrafluoroborate; potassium carbonate In water; toluene at 20℃; for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere;99%
With 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate; sodium carbonate In tert-butyl alcohol at 20 - 120℃; for 18h; Suzuki-Miyaura coupling;98%
With potassium phosphate; (NC5H3(N2C7H4(CH2)3CH3)2)NiBr(1+)*Br(1-)=Ni(NC5H3(N2C7H4(CH2)3CH3)2)Br2; triphenylphosphine In 1,4-dioxane at 100℃; for 24h; Suzuki-Miyaura coupling;91%
ethanol
64-17-5

ethanol

4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With 2C2H4O2*C40H36N2O2Pd; potassium hydroxide at 50℃; for 1h; Suzuki coupling;99%
4-iodobenzoic acid ethyl ester
51934-41-9

4-iodobenzoic acid ethyl ester

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With Pd/C; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;99%
Stage #1: phenylboronic acid With diethylzinc; lithium chloride In tetrahydrofuran; toluene at 23℃; for 1h; Inert atmosphere; Glovebox;
Stage #2: 4-iodobenzoic acid ethyl ester In tetrahydrofuran; toluene at 110℃; for 24h; Inert atmosphere; Glovebox;
95%
With triethylamine In 1,4-dioxane; water at 100℃; for 1h; Suzuki-Miyaura Coupling; Microwave irradiation; Green chemistry;94%
ethyl 4-[(fluorosulphonyl)oxy]benzoate

ethyl 4-[(fluorosulphonyl)oxy]benzoate

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With palladium diacetate; triethylamine In water at 20℃; for 2h; Suzuki-Miyaura Coupling;99%
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane at 80℃; for 15h; Reagent/catalyst; Suzuki Coupling;92%
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane at 80℃; for 15h; Reagent/catalyst; Inert atmosphere;40%
(4-(ethoxycarbonyl)phenyl)zinc(II) iodide lithium chloride

(4-(ethoxycarbonyl)phenyl)zinc(II) iodide lithium chloride

methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
Stage #1: (4-(ethoxycarbonyl)phenyl)zinc(II) iodide lithium chloride With trans-[1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene]PdCl2(NC5H5) In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere;
Stage #2: methyl-phenyl-thioether In tetrahydrofuran; acetonitrile at 20℃; for 4h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;
99%
phenylmanganese(II) chloride
71478-47-2

phenylmanganese(II) chloride

p-(ethoxycarbonyl)phenyl triflate
125261-30-5

p-(ethoxycarbonyl)phenyl triflate

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
1,2-dimethoxyethane; bis(diphenylphosphino)propanepalladium(II) dichloride In tetrahydrofuran at 20℃; for 0.0833333h;98%
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; 1,2-dimethoxyethane at 0 - 20℃; for 0.5h;88%
ethyl 4-chlorobenzoate
7335-27-5

ethyl 4-chlorobenzoate

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With 2-chloro-1,3-[di-(2,6-diisopropyl)phenyl]-1,3,2-diazaphospholidine; tris-(dibenzylideneacetone)dipalladium(0); cesium fluoride In 1,4-dioxane at 80℃; for 18h; Suzuki-Miyaura cross-coupling; Inert atmosphere;98%
With potassium carbonate In toluene at 100℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere;98%
With caesium carbonate In N,N-dimethyl acetamide at 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;94%
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

potassium phenyltrifluoborate

potassium phenyltrifluoborate

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With choline chloride; palladium diacetate; sodium carbonate; glycerol at 60℃; for 5h; Suzuki-Miyaura Coupling;98%
With potassium carbonate; triphenylphosphine In methanol at 50℃; for 24h; Suzuki-Miyaura coupling;85%
With palladium diacetate; potassium carbonate In ethanol; water at 40℃; for 15h; Solvent; Reagent/catalyst; Temperature; Suzuki Coupling; Green chemistry;
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

phenylzinc iodide
23665-09-0

phenylzinc iodide

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride; tetrabutylammomium bromide for 4h; Negishi Coupling; Milling;98%
With lithium chloride In tetrahydrofuran; toluene at 110℃; for 48h; Schlenk technique; Inert atmosphere;83%
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

4-bromo-1,1'-biphenyl
92-66-0

4-bromo-1,1'-biphenyl

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With triethylamine at 70℃; under 760.051 Torr; for 3h; Catalytic behavior;98%
ethanol
64-17-5

ethanol

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h; Reagent/catalyst; Solvent; Concentration;97%
With sulfuric acid
With hydrogenchloride
4-bromo-1,1'-biphenyl
92-66-0

4-bromo-1,1'-biphenyl

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With dmap; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.333333h; Microwave irradiation;97%
Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; palladium diacetate; caesium carbonate; triphenylphosphine In tetrahydrofuran at 20 - 60℃; for 5h; Inert atmosphere;96%
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; palladium diacetate; caesium carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; for 4h; Inert atmosphere;96%
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

phenylmagnesium chloride
100-59-4

phenylmagnesium chloride

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
Stage #1: phenylmagnesium chloride With titanium(IV) tetraethanolate In tetrahydrofuran at 0℃;
Stage #2: Ethyl 4-bromobenzoate With 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; bis(acetylacetonate)nickel(II) In tetrahydrofuran at 25℃; for 3h; Further stages.;
95%
p-aminoethylbenzoate
94-09-7

p-aminoethylbenzoate

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
Stage #1: p-aminoethylbenzoate With tert.-butylnitrite; boron trifluoride diethyl etherate In methanol at 0℃; for 0.5h; Schlenk technique;
Stage #2: phenylboronic acid In methanol at 0 - 60℃; for 5h; Reagent/catalyst; Solvent; Temperature; Schlenk technique;
95%
Stage #1: p-aminoethylbenzoate With tert.-butylnitrite; acetic acid In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: phenylboronic acid With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane In N,N-dimethyl-formamide at 90℃; for 10h; Inert atmosphere;
50%
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

diphenylzinc
1078-58-6

diphenylzinc

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With tripiperidino-phosphine; nickel dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 60℃; for 0.5h; Negishi cross-coupling reaction;95%
Methyl 4-chlorobenzoate
1126-46-1

Methyl 4-chlorobenzoate

phenylboronic acid
98-80-6

phenylboronic acid

A

methyl 4-phenylbenzoate
720-75-2

methyl 4-phenylbenzoate

B

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With 5%-palladium/activated carbon; N,N′-bis(2,6-diisopropylphenyl)imidazolylidene hydrochloride; sodium hydroxide; phosphorous acid trimethyl ester In ethanol at 80℃; for 5h; Suzuki Coupling; Inert atmosphere;A 95%
B n/a
ethyl 4-chlorobenzoate
7335-27-5

ethyl 4-chlorobenzoate

2-(2-hydroxyprop-2-yl)cyclohexyl(dimethyl)phenylsilane

2-(2-hydroxyprop-2-yl)cyclohexyl(dimethyl)phenylsilane

A

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

C11H22OSi

C11H22OSi

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,2-dimethoxyethane)dichloronickel(II); caesium carbonate; zinc; tricyclohexylphosphine In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 20 - 75℃; for 30h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere; chemoselective reaction;A 82%
B 93%
N-hydroxy-[1,1'-biphenyl]-4-carboxamide
106359-54-0

N-hydroxy-[1,1'-biphenyl]-4-carboxamide

2,2-diethoxypropane
126-84-1

2,2-diethoxypropane

A

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

B

5,5-dimethyl-3-(p-biphenyl)-1,4,2-dioxazole

5,5-dimethyl-3-(p-biphenyl)-1,4,2-dioxazole

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane at 20℃; for 4h;A n/a
B 92%
iodobenzene
591-50-4

iodobenzene

4-(ethoxycarbonyl)phenylzinc iodide
131379-16-3

4-(ethoxycarbonyl)phenylzinc iodide

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
With lithium chloride In tetrahydrofuran; toluene at 110℃; for 48h; Schlenk technique; Inert atmosphere;92%
methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

(4-(ethoxycarbonyl)phenyl)zinc(ll) bromide
131379-15-2

(4-(ethoxycarbonyl)phenyl)zinc(ll) bromide

ethyl 4-phenylbenzoate
6301-56-0

ethyl 4-phenylbenzoate

Conditions
ConditionsYield
Stage #1: (4-(ethoxycarbonyl)phenyl)zinc(ll) bromide With trans-[1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene]PdCl2(NC5H5); lithium chloride In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere;
Stage #2: methyl-phenyl-thioether In tetrahydrofuran; acetonitrile at 20℃; for 5h; Inert atmosphere;
92%

6301-56-0Relevant articles and documents

Palladium phosphine complex catalysts immobilized on silica via a tripodal linker unit for the Suzuki-Miyaura coupling reactions of aryl chlorides

Fukaya, Norihisa,Onozawa, Syun-Ya,Ueda, Masae,Miyaji, Takayuki,Takagi, Yukio,Sakakura, Toshiyasu,Yasuda, Hiroyuki

, p. 7 - 12 (2014)

Silica-immobilized palladium phosphine complex catalysts bearing a tripodal linker unit were tested for their ability to facilitate the Suzuki-Miyaura coupling reactions of aryl chlorides. The catalyst containing the tripodal linker with a trimethylsilyl capping group on the residual surface silanol groups displayed better catalytic activities and lower palladium and phosphorus leaching levels than the catalysts bearing a conventional trialkoxy-type linker.

Synthesis of Pd/SiO2 nanobeads for use in suzuki coupling reactions by reverse micelle sol-gel process

Kim, Mijong,Heo, Eunjung,Kim, Aram,Park, Ji Chan,Song, Hyunjoon,Park, Kang Hyun

, p. 588 - 593 (2012)

Pd/SiO2 nanobeads containing tiny Pd clusters with a diameter of about 2 nm were prepared via a sol-gel process for SiO2 by using a water-in-oil microemulsion with Pd complexes and subsequent hydrogen reduction by heat treatment. The Pd/SiO2 nanostructures were employed in Suzuki coupling reactions with various substrates, and they served as good catalysts in these reactions.

Heterogeneous High-Loading Hyperbranched Polyglycidol with Peripheral NHC–Pd Complex: Synthesis and Application as Catalyst in Suzuki Coupling Reaction

Anjali,Sreekumar

, p. 1952 - 1964 (2019)

Abstract: A new polymer-supported highly functionalized dendritic polyether with peripheral NHC–Pd complex was developed by the simple anionic ring opening polymerization of glycidol on bis(3-hydroxypropyl) amine grafted Merrifield resin and its subsequent functional modification of hydroxyl group to NHC–Pd complex. The polymeric material had high stability and swelling capacity in a wide range of solvents, even in water. Similar to supported higher generation dendrimer, the newly developed system showed high palladium content with uniformly distributed and well isolated metal nanocentres. The palladium content was found to be 2.02?mmol/g which was comparatively higher than other heterogeneous NHC–Pd based catalysts and the polymer was used as heterogeneous palladium catalyst for Suzuki coupling reaction. Various factors affecting the catalyst’s performance were studied. The high availability and increased accessibility of catalytic sites, stability and dendrimer like property of the polymeric support, reusability, better resistance to metal leaching, easy synthesis etc. are the important features of this newly synthesized catalytic system. Graphical Abstract: [Figure not available: see fulltext.]

Aminomethylpyridinequinones as new ligands for PEPPSI-type complexes

Gajda, Roman,Poater, Albert,Brotons-Rufes, Artur,Planer, Sebastian,Wo?niak, Krzysztof,Grela, Karol,Kajetanowicz, Anna

, p. 138 - 156 (2021/03/22)

A set of six new catalysts possessing quinone moieties in a pyridine ligand was synthesized and fully characterized by standard analytical techniques, including X-Ray crystallography. The results obtained in Suzuki and Mizoroki–Heck cross-coupling reactions catalyzed by quinone-based compounds were comparable to these obtained in the presence of the original PEPPSI complex designed by Organ. DFT calculations allow to see the structural and electronic factors to describe their similarity. On the other hand, steric maps and NCI plots were the tools to have a more global view of the systems studied, leaving the sphere of reactivity around the metal.

1,2,4-Triazole-3-thione compounds with a 4-ethyl alkyl/aryl sulfide substituent are broad-spectrum metallo-β-lactamase inhibitors with re-sensitization activity

Becker, Katja,Benvenuti, Manuela,Bossis, Guillaume,Conde, Pierre-Alexis,Crowder, Michael W.,Dillenberger, Melissa,Docquier, Jean-Denis,Gavara, Laurent,Hernandez, Jean-Fran?ois,Legru, Alice,Mangani, Stefano,Pozzi, Cecilia,Sannio, Filomena,Tassone, Giusy,Thomas, Caitlyn A.,Verdirosa, Federica

supporting information, (2021/10/12)

Metallo-β-lactamases (MBLs) are important contributors of Gram-negative bacteria resistance to β-lactam antibiotics. MBLs are highly worrying because of their carbapenemase activity, their rapid spread in major human opportunistic pathogens while no clinically useful inhibitor is available yet. In this context, we are exploring the potential of compounds based on the 1,2,4-triazole-3-thione scaffold as an original ligand of the di-zinc active sites of MBLs, and diversely substituted at its positions 4 and 5. Here, we present a new series of compounds substituted at the 4-position by a thioether-containing alkyl chain with a carboxylic and/or an aryl group at its extremity. Several compounds showed broad-spectrum inhibition with Ki values in the μM to sub-μM range against VIM-type enzymes, NDM-1 and IMP-1. The presence of the sulfur and of the aryl group was important for the inhibitory activity and the binding mode of a few compounds in VIM-2 was revealed by X-ray crystallography. Importantly, in vitro antibacterial susceptibility assays showed that several inhibitors were able to potentiate the activity of meropenem on Klebsiella pneumoniae clinical isolates producing VIM-1 or VIM-4, with a potentiation effect of up to 16-fold. Finally, a selected compound was found to only moderately inhibit the di-zinc human glyoxalase II, and several showed no or only moderate toxicity toward several human cells, thus favourably completing a promising behaviour.

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