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214360-73-3

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214360-73-3 Usage

Chemical Properties

almost white to light beige crystalline powder

Uses

Different sources of media describe the Uses of 214360-73-3 differently. You can refer to the following data:
1. suzuki reaction
2. 4-Aminophenylboronic acid pinacol ester can be used as a reagent for:The preparation of substituted 3-phenyl-4H-1-benzopyran-4-ones by reacting with iodochromones via Pd catalyzed Suzuki-Miyaura cross-coupling reaction. Mercury(II) detection by fluorometry with new fluorogenic indicators based on through-bond energy transfer from pentaquinone to rhodamine. Rhodium-catalyzed amination reactions. Palladium-catalyzed Suzuki cross-coupling to synthesize potential antitubercular and antimicrobial compounds. It can also be used to prepare: Hexaphenylbenzene derivatives as a potential bioprobe and multichannel keypad system.Pyromellitic diimide-based polymer as matrix for solution-processable n-channel field-effect transistors. Alternating copolymers of oligoarylenes and naphthalene bisimides as low band-gap semiconductors with electrochemical and spectroelectrochemical behavior. γ-secretase modulators in the treatment of amyloid β formation.

Check Digit Verification of cas no

The CAS Registry Mumber 214360-73-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,1,4,3,6 and 0 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 214360-73:
(8*2)+(7*1)+(6*4)+(5*3)+(4*6)+(3*0)+(2*7)+(1*3)=103
103 % 10 = 3
So 214360-73-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H18BNO2/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8H,14H2,1-4H3

214360-73-3 Well-known Company Product Price

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  • TCI America

  • (T1951)  4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline  >98.0%(GC)

  • 214360-73-3

  • 1g

  • 490.00CNY

  • Detail
  • TCI America

  • (T1951)  4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline  >98.0%(GC)

  • 214360-73-3

  • 5g

  • 1,690.00CNY

  • Detail
  • Alfa Aesar

  • (H51666)  4-Aminobenzeneboronic acid pinacol ester, 98%   

  • 214360-73-3

  • 1g

  • 587.0CNY

  • Detail
  • Alfa Aesar

  • (H51666)  4-Aminobenzeneboronic acid pinacol ester, 98%   

  • 214360-73-3

  • 5g

  • 2107.0CNY

  • Detail
  • Aldrich

  • (518751)  4-Aminophenylboronicacidpinacolester  97%

  • 214360-73-3

  • 518751-1G

  • 555.75CNY

  • Detail
  • Aldrich

  • (518751)  4-Aminophenylboronicacidpinacolester  97%

  • 214360-73-3

  • 518751-5G

  • 2,150.46CNY

  • Detail

214360-73-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Aminophenylboronic acid pinacol ester

1.2 Other means of identification

Product number -
Other names 4-METHYLPHENYLBORONIC ACID PINACOLATE

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:214360-73-3 SDS

214360-73-3Synthetic route

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene
171364-83-3

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;99%
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 4h;98%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 4h;97%
4-bromo-aniline
106-40-1

4-bromo-aniline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With 10H-phenothiazine; caesium carbonate In acetonitrile for 48h; Irradiation; Sealed tube; Inert atmosphere;97%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide at 150℃; for 0.366667h; microwave irradiation;85%
With bis(tri-t-butylphosphine)palladium(0); potassium acetate In water at 20℃; for 24h; Reagent/catalyst; Miyaura Borylation Reaction; Inert atmosphere;85%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With caesium carbonate In methanol for 60h; Reflux; Inert atmosphere;96%
With pyridine; C50H44CuN4OP2(1+)*F6P(1-); N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;87%
With 10H-phenothiazine; caesium carbonate In acetonitrile for 48h; Irradiation; Sealed tube; Inert atmosphere;80%
C18H34BNO2Si2

C18H34BNO2Si2

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 20℃; for 1h;91%
4-bromo-aniline
106-40-1

4-bromo-aniline

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In 1,4-dioxane at 120℃; for 12h; Time; Schlenk technique; Inert atmosphere;90%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In 1,4-dioxane at 120℃; for 12h; Schlenk technique; Inert atmosphere;90%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In 1,4-dioxane at 120℃; for 12h; Inert atmosphere;89%
2,2,2-trifluoro-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide
864754-08-5

2,2,2-trifluoro-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
87.1%
p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With dichlorobis(chlorodi-tert-butylphosphine) palladium(II); triethylamine In toluene for 2h; Inert atmosphere; Reflux;83%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine In 1,4-dioxane at 90℃; for 1.5h; Inert atmosphere;80%
With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 80℃; for 8h;75 %Chromat.
2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
73852-88-7

2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane In toluene at 100℃; for 2h; Glovebox; Sealed tube;80%
Multi-step reaction with 2 steps
1: chlorotris(triphenylphosphine)cobalt(I); bis[2-(diphenylphosphino)phenyl] ether / toluene / 12 h / 100 °C
2: hydrogenchloride; water / methanol / 1 h / 20 °C
View Scheme
Triisopropyl borate
5419-55-6

Triisopropyl borate

2-(4-bromophenyl)-1,1,1,3,3,3-hexamethyldisilazane
5089-33-8

2-(4-bromophenyl)-1,1,1,3,3,3-hexamethyldisilazane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
Stage #1: 2-(4-bromophenyl)-1,1,1,3,3,3-hexamethyldisilazane With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 25℃; for 4.5h; Inert atmosphere;
Stage #3: With 2,3-dimethyl-2,3-butane diol; acetic acid In tetrahydrofuran at 20℃; for 0.75h; pH=5; Inert atmosphere;
79%
(4-aminophenyl)boronic acid hydrochloride

(4-aminophenyl)boronic acid hydrochloride

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With magnesium sulfate In tetrahydrofuran at 20℃; for 5h;76%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

4-bromo-N-(diphenylmethylidene)aniline
53847-33-9

4-bromo-N-(diphenylmethylidene)aniline

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
Stage #1: 4-bromo-N-(diphenylmethylidene)aniline With C12H27Mg(1-)*Li(1+) In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; Green chemistry; Large scale;
Stage #2: With Trimethyl borate In tetrahydrofuran at -20 - 25℃; for 2.5h; Inert atmosphere; Green chemistry; Large scale;
Stage #3: 2,3-dimethyl-2,3-butane diol Reagent/catalyst; Temperature; Green chemistry; Large scale; Further stages;
70%
4-fluoroaniline
371-40-4

4-fluoroaniline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane In toluene at 80℃; for 12h; Inert atmosphere; Schlenk technique;68%
With tetramethylammonium fluoride; 2-mercaptopyridine sodium salt In acetonitrile at 30 - 35℃; for 24h; Irradiation; Inert atmosphere;52%
1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With tert.-butylnitrite In acetonitrile at 80℃; for 2h;62%
With tert.-butylnitrite In acetonitrile at 80℃; for 2h;62%
With tert.-butylnitrite In acetonitrile at 80℃; for 2h;62%
With tert.-butylnitrite In acetonitrile at 80℃; for 2h;62%
Stage #1: 1,4-phenylenediamine With hydrogenchloride; methanol; sodium nitrite In water at 0 - 5℃; for 0.5h; Sandmeyer Reaction; Green chemistry;
Stage #2: bis(pinacol)diborane In water at 20℃; for 1h; Sandmeyer Reaction; Green chemistry;
53%
4-amino-N,N,N-trimethylbenzenaminium trifluoromethanesulfonate

4-amino-N,N,N-trimethylbenzenaminium trifluoromethanesulfonate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); potassium tert-butylate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In 2-ethoxy-ethanol; toluene at 50℃; for 24h; Schlenk technique; Inert atmosphere;62%
4-chloro-aniline
106-47-8

4-chloro-aniline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With Co(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)2Cl2; potassium methanolate In tert-butyl methyl ether at 50℃; for 8h;60%
With potassium acetate In isopropyl alcohol at 82℃; for 2h; Suzuki-Miyaura Coupling;75 %Chromat.
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Triisopropyl borate
5419-55-6

Triisopropyl borate

(4-(bis(trimethylsilyl)amino)phenyl)magnesium bromide
756822-47-6

(4-(bis(trimethylsilyl)amino)phenyl)magnesium bromide

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
Stage #1: Triisopropyl borate; (4-(bis(trimethylsilyl)amino)phenyl)magnesium bromide In tetrahydrofuran at -70 - -60℃; for 5h; Inert atmosphere;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;
Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran at 20℃;
59%
6-methyl-1-oxo-2-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carboxylic acid
627093-70-3

6-methyl-1-oxo-2-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carboxylic acid

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With triethylamine In DMF (N,N-dimethyl-formamide); toluene Reduced pressure;45%
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-bromo-aniline
106-40-1

4-bromo-aniline

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
Stage #1: 4-bromo-aniline With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 24h;
42.2%
4-Amino-thiobenzoesaeure-S-ethylester
102879-36-7

4-Amino-thiobenzoesaeure-S-ethylester

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With [Rh(OH)(cod)]2; tributylphosphine; potassium acetate at 80℃; for 24h; Inert atmosphere; Glovebox;32.4%
4-bromo-aniline
106-40-1

4-bromo-aniline

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / 0 °C / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 4.5 h / -78 - 25 °C / Inert atmosphere
2.3: 0.75 h / 20 °C / pH 5 / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / tetrahydrofuran / 0 - 60 °C / Inert atmosphere
1.2: -10 - 0 °C
2.1: magnesium; iodine / tetrahydrofuran / 2 h / 50 °C / Inert atmosphere; Reflux
3.1: tetrahydrofuran / 5 h / -70 - -60 °C / Inert atmosphere
3.2: 2 h / 20 °C
3.3: 20 °C
View Scheme
aniline
62-53-3

aniline

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

B

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

C

3-aminophenylboronic acid pinacolate
210907-84-9

3-aminophenylboronic acid pinacolate

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; 1,2,3,4,5,6,7,8,9,10,11,12-dodecahydrotriphenylene In tetrahydrofuran at 80℃; for 16h; Inert atmosphere; Glovebox; regioselective reaction;
4-nitro-aniline
100-01-6

4-nitro-aniline

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2-(4-biphenylyl)-5-phenyloxazole; tert.-butylnitrite / acetonitrile / 4 h / 20 °C
2: 5%-palladium/activated carbon; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr
View Scheme
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2-(4-biphenylyl)-5-phenyloxazole; tert.-butylnitrite / acetonitrile / 4 h / 20 °C
2: 5%-palladium/activated carbon; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr
View Scheme
(4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester
330793-01-6

(4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With hydrogenchloride In ethyl acetate at 20℃; for 4h;
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

(4-aminophenyl)boronic acid
89415-43-0

(4-aminophenyl)boronic acid

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With magnesium sulfate In tetrahydrofuran at 20℃; for 5h;
1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: formic acid; sodium cyanoborohydride / methanol / 16 h / 0 - 20 °C / pH 3 - 4 / Inert atmosphere
1.2: 0 °C / Inert atmosphere
2.1: bis(1,5-cyclooctadiene)nickel(0); 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; potassium tert-butylate / toluene; 2-ethoxy-ethanol / 24 h / 50 °C / Schlenk technique; Inert atmosphere
View Scheme
S-(p-nitrobenzoyl)mercaptoethane
24524-95-6

S-(p-nitrobenzoyl)mercaptoethane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tin(II) chloride dihdyrate / ethyl acetate / 4 h / Inert atmosphere; Reflux
2: [Rh(OH)(cod)]2; tributylphosphine; potassium acetate / 24 h / 80 °C / Inert atmosphere; Glovebox
View Scheme
acetic anhydride
108-24-7

acetic anhydride

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide
214360-60-8

N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

Conditions
ConditionsYield
at 20℃; for 1h;100%
In dichloromethane at 20℃; for 10h;87%
for 1h;
1-bromo-4-(2,2,2-trifluoroethyl)benzene
155820-88-5

1-bromo-4-(2,2,2-trifluoroethyl)benzene

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4-[4'-(2,2,2-trifluoroethyl)-4-biphenylyl]amine

4-[4'-(2,2,2-trifluoroethyl)-4-biphenylyl]amine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 17h; Suzuki coupling;100%
dichlorobenzenesulfonyl chloride
82417-45-6

dichlorobenzenesulfonyl chloride

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

2,3-dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide
912675-28-6

2,3-dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide

Conditions
ConditionsYield
With pyridine at 20℃; for 15h;100%
With pyridine In dichloromethane at 20 - 25℃; for 20h;77%
With pyridine In dichloromethane at 20 - 25℃; for 20h;77%
6-chloro-2-ethoxy-N-methylnicotinamide

6-chloro-2-ethoxy-N-methylnicotinamide

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

6-(4-aminophenyl)-2-ethoxy-N-methylnicotinamide
1138322-13-0

6-(4-aminophenyl)-2-ethoxy-N-methylnicotinamide

Conditions
ConditionsYield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol; water for 16h; Inert atmosphere; Reflux;100%
7-bromo-2-chloroquinoxaline
89891-65-6

7-bromo-2-chloroquinoxaline

4-(piperazin-1-yl)pyridine
1008-91-9

4-(piperazin-1-yl)pyridine

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenlamine
1271847-04-1

4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenlamine

Conditions
ConditionsYield
Stage #1: 7-bromo-2-chloroquinoxaline; 4-(piperazin-1-yl)pyridine With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20 - 160℃; Microwave irradiation;
Stage #2: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With potassium carbonate; tris-(o-tolyl)phosphine; palladium diacetate In 1-methyl-pyrrolidin-2-one at 140℃; Microwave irradiation;
100%
C11H13BrN4O
1252598-01-8

C11H13BrN4O

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

C17H19N5O
1252597-72-0

C17H19N5O

Conditions
ConditionsYield
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl ether, 1,2- at 130℃; for 1h; Microwave irradiation;100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane at 130℃; for 1h; Microwave irradiation;100%
methyl chloroformate
79-22-1

methyl chloroformate

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

methyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate
844500-75-0

methyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Conditions
ConditionsYield
With pyridine In 1,2-dichloro-ethane at 0 - 60℃;100%
6-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-2-chloroquinoxaline
1437281-38-3

6-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-2-chloroquinoxaline

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4-(6-(2-((tert-butyldimethylsilyl)oxy)ethoxy)quinoxalin-2-yl)aniline
1437281-40-7

4-(6-(2-((tert-butyldimethylsilyl)oxy)ethoxy)quinoxalin-2-yl)aniline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 4h; Reflux;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 4h; Reflux;100%
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

(E)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-(o-tolyl)methanimine

(E)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-(o-tolyl)methanimine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 18h; Inert atmosphere; Molecular sieve;100%
glycolic Acid
79-14-1

glycolic Acid

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

C14H20BNO4

C14H20BNO4

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 36h;100%
2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

2′,4′,6′-trimethylbiphenyl-4-amine
66818-61-9

2′,4′,6′-trimethylbiphenyl-4-amine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane for 17h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;100%
methyl 4-iodobenzoate
619-44-3

methyl 4-iodobenzoate

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

methyl 4’-amino-[1,1’-biphenyl]-4-carboxylate
5730-76-7

methyl 4’-amino-[1,1’-biphenyl]-4-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 10h;100%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4-(methylsulfonylamino)phenyl boronic acid
380430-57-9

4-(methylsulfonylamino)phenyl boronic acid

Conditions
ConditionsYield
Stage #1: methanesulfonyl chloride; 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With pyridine In dichloromethane at 0 - 20℃;
Stage #2: With water In dichloromethane
99%
1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene
69922-27-6

1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

N-(2-fluoro-5-trifluoromethylphenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea
796967-62-9

N-(2-fluoro-5-trifluoromethylphenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃;98.8%
In tetrahydrofuran at 20℃; for 0.5h;85%
In dichloromethane at 20℃;
1-isocyanato-3-trifluoromethyl-benzene
329-01-1

1-isocyanato-3-trifluoromethyl-benzene

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

N-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]-N'-(3-trifluoromethylphenyl)urea
796967-48-1

N-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]-N'-(3-trifluoromethylphenyl)urea

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;98%
In dichloromethane at 20℃;
With triethylamine In dichloromethane at 20℃;
2,5-dichlorobenzenesulphonyl chloride
5402-73-3

2,5-dichlorobenzenesulphonyl chloride

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

2,5-dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide
1426214-54-1

2,5-dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 1h;98%
With pyridine In dichloromethane at 20 - 25℃; for 16h;17.9 g
With pyridine In dichloromethane at 20 - 25℃; for 16h;17.9 g
1,3,6,8-tetrabromopyrene
128-63-2

1,3,6,8-tetrabromopyrene

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4,4’,4’’,4’’’-(pyrene-1,3,6,8-tetrayl) tetra aniline
1610471-69-6

4,4’,4’’,4’’’-(pyrene-1,3,6,8-tetrayl) tetra aniline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 115℃; Inert atmosphere;98%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 72h; Schlenk technique; Inert atmosphere; Reflux;94%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 115℃; for 72h; Inert atmosphere;90%
succinic acid anhydride
108-30-5

succinic acid anhydride

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4-oxo-4-[(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)amino]butanoic acid
480424-98-4

4-oxo-4-[(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)amino]butanoic acid

Conditions
ConditionsYield
In chloroform at 20℃; for 4h;98%
3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide
50978-45-5

3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)formamide

N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)formamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.166667h; Solvent; Time;98%
5-bromo-2-(2-fluorophenyl)thiazole

5-bromo-2-(2-fluorophenyl)thiazole

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4-[2-(2-fluorophenyl)thiazol-5-yl]phenylamine

4-[2-(2-fluorophenyl)thiazol-5-yl]phenylamine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere;98%
[5,15-dibromo-10,20-bis(2,6-dioctoxyphenyl)porphinato]zinc(II)

[5,15-dibromo-10,20-bis(2,6-dioctoxyphenyl)porphinato]zinc(II)

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

C91H124N6O4Zn

C91H124N6O4Zn

Conditions
ConditionsYield
Stage #1: [5,15-dibromo-10,20-bis(2,6-dioctoxyphenyl)porphinato]zinc(II) With tetrakis(triphenylphosphine) palladium(0) In toluene at 20℃; for 0.5h; Sonogashira Cross-Coupling;
Stage #2: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With sodium carbonate In ethanol; water; toluene at 100℃; for 5h; Sonogashira Cross-Coupling;
97.22%
phenyl isocyanate
103-71-9

phenyl isocyanate

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

N-phenyl-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea
819056-67-2

N-phenyl-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea

Conditions
ConditionsYield
In toluene at 50℃; for 16h;97%
With triethylamine In dichloromethane at 20℃;70%
With 4-methyl-morpholine In tetrahydrofuran
5-chloro-3-cyclopropyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine
1173205-24-7

5-chloro-3-cyclopropyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4-(3-cyclopropyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl)aniline
1173205-23-6

4-(3-cyclopropyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl)aniline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 140℃; for 0.75h; Suzuki coupling; Microwave irradiation;97%
2-chloro-7-(2,2-dimethoxyethyl)-4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidine
1202885-77-5

2-chloro-7-(2,2-dimethoxyethyl)-4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidine

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4-[7-(2,2-dimethoxyethyl)-4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidin-2-yl]aniline
1202885-78-6

4-[7-(2,2-dimethoxyethyl)-4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidin-2-yl]aniline

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 130℃; for 0.5h; Suzuki Coupling; Microwave irradiation;97%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 130℃; for 0.5h; Suzuki coupling; Microwave irradiation;97%
4-[1-(benzenesulfonyl)cyclopropyl]-2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine
1101819-64-0

4-[1-(benzenesulfonyl)cyclopropyl]-2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

4-[4-[1-(benzenesulfonyl)cyclopropyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline
1101819-63-9

4-[4-[1-(benzenesulfonyl)cyclopropyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide at 80 - 95℃; for 5h; Inert atmosphere;97%
3-chloro-5-(3,4-dimethoxyphenyl)pyrazin-2-amine

3-chloro-5-(3,4-dimethoxyphenyl)pyrazin-2-amine

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

3-(4-aminophenyl)-5-(3,4-dimethoxyphenyl) pyrazin-2-amine

3-(4-aminophenyl)-5-(3,4-dimethoxyphenyl) pyrazin-2-amine

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 100℃; for 4h;96.8%
para-fluorophenyl isocyanate
1195-45-5

para-fluorophenyl isocyanate

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

N-(4-fluorophenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea
819056-61-6

N-(4-fluorophenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea

Conditions
ConditionsYield
at 20℃;96%
In dichloromethane at 20℃;
In dichloromethane Alkaline conditions;
In dichloromethane at 0 - 20℃; Alkaline conditions;

214360-73-3Relevant articles and documents

Synthesis of a photostable near-infrared-absorbing photosensitizer for selective photodamage to cancer cells

Hsieh, Tung-Sheng,Wu, Jhen-Yi,Chang, Cheng-Chung

, p. 9709 - 9715 (2014)

A new class of near-infrared (NIR)-absorptive (>900 nm) photosensitizer based on a phenothiazinium scaffold is reported. The stable solid compound, o-DAP, the oxidative form of 3,7-bis(4-methylaminophenyl)-10H-phenothiazine, can generate reactive oxygen species (ROS, singlet oxygen and superoxide) under appropriate irradiation conditions. After biologically evaluating the intracellular uptake, localization, and phototoxicity of this compound, it was concluded that o-DAP is photostable and a potential selective photodynamic therapy (PDT) agent under either NIR or white light irradiation because its photodamage is more efficient in cancer cells than in normal cells and is without significant dark toxicity. This is very rare for photosensitizers in PDT applications. Selective PDT agent: A photostable near-infrared (NIR)-absorptive phenothiazinium derivative, o-DAP, has been successfully synthesized and demonstrated to be a potential tumor-specific NIR-absorptive (>900 nm) photosensitizer for photodynamic therapy (PDT; see figure). This compound is expected to become a PDT reagent in a solar environment.

Terphenyl based 'Turn On' fluorescent sensor for mercury

Bhalla, Vandana,Tejpal, Ruchi,Kumar, Manoj,Puri, Rajiv Kumar,Mahajan, Rakesh K.

, p. 2649 - 2652 (2009)

New terphenyl-based derivative 4 with pyrene as a fluorophore has been synthesized and examined for its cation recognition abilities toward various cations by NMR and fluorescence spectroscopy. The results show that it has very high binding affinity (log

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming

supporting information, p. 1618 - 1629 (2021/01/25)

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Synthesis, crystal structure and DFT study of a novel compound N-(4-(2,4-dimorpholinopyrido[2,3-d]pyrimidin-6-yl)phenyl)pyrrolidine-1-carboxamide

Zhou, Zhixu,Liu, Ye,Ren, Qian,Yu, Dehou,Lu, Hongguang

, (2021/03/22)

In this paper, the compound N-(4-(2,4-dimorpholinopyrido[2,3-d]pyrimidin-6-yl)phenyl) pyrrolidine-1-carboxamide was synthesized and characterized using 13C NMR, 1H NMR, FT-IR and MS as well as by a single crystal X-ray structural analysis. Additionally, the structure of the single crystal was confirmed using X-ray diffraction. The packing of the molecules in the solid state is dominated by hydrogen bonds. The optimized structure of the compound was computed via DFT using the B3LYP functional with the 6-311G(2d, p) as basis set and compared with that determined using X-ray diffraction. The results show that the crystal structure confirmed using X-ray diffraction is consistent with the molecular structure optimized using DFT. In addition, the anti-proliferative activity of the title compound on A375 cells was studied, and the inhibition rate at a concentration of 5 μM was 12.89%. Furthermore, molecular docking was performed to analyze the binding mode of the title compound with PI3Kγ.

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