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Chemical Structure| 1660-93-1 Chemical Structure| 1660-93-1
Chemical Structure| 1660-93-1

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Synonyms: TMPhen

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D' ; Angelo, Kyan A ; La, Chris ; Kotecki, Brian ; Wilson, Jake W ; Karmel, Caleb , et al.

Abstract: The functionalization of C−H bonds enables the modification of complex molecules, often with the intention of forming compound libraries. The borylation of aryl C−H bonds is a widely used class of C−H bond functionalization, and conventional catalyst systems for the borylation of C−H bonds consist of an iridium source and an N,N-ligand, in conjunction with pinacolborane, to form the active iridium(III) tris(boryl) catalyst. These multicomponent catalyst systems complicate borylation reactions at large and small scales, due to the air sensitivity of the most common iridium precursor [Ir(cod)OMe]2, and, particularly on small scale, the challenges associated with dispensing multiple components with differing solubilities or that are air-sensitive. We describe the discovery of an air-stable, single-component iridium precatalyst, [(tmphen)Ir(coe)2Cl], that generates the same active iridium(III) tris(boryl) catalyst and reacts with higher turnovers, comparable selectivity, and similar scope to those of known catalyst systems for the borylation of aryl and heteroaryl C−H bonds. We show how the development of this precatalyst enables reactions to be run on submicromole scale in a high-throughput experimentation format in conjunction with ChemBead technology, and with a second diversification step that illustrates the potential to diversify structures by chemical sequences involving catalytic reactions, including C−H bond functionalizations, on submicromole scales in the same reaction vessel.

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Product Details of 3,4,7,8-Tetramethyl-1,10-phenanthroline

CAS No. :1660-93-1
Formula : C16H16N2
M.W : 236.31
SMILES Code : CC1=CN=C2C(C=CC3=C(C)C(C)=CN=C23)=C1C
Synonyms :
TMPhen
MDL No. :MFCD00004974
InChI Key :NPAXPTHCUCUHPT-UHFFFAOYSA-N
Pubchem ID :74265

Safety of 3,4,7,8-Tetramethyl-1,10-phenanthroline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of 3,4,7,8-Tetramethyl-1,10-phenanthroline

* 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 [ 1660-93-1 ]

[ 1660-93-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1660-93-1 ]
  • europium(III) chloride hexahydrate [ No CAS ]
  • [ 39207-65-3 ]
  • Eu(iButCHex)3*3,4,7,8-tetramethylphenanthroline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; water; General procedure: In the preparation of the Ln(CA)3·Phn and Ln(CA)3·Bpy adducts the 3-N NaOH water solution and an ethanol solution of Phn or Bpy were added to an ethanol solution of CA. Then, a water?ethanol (1:1) solution of LnCl3·6H2O was drop by drop added to the previous mixture at heating in a water bath (at 60?70°C) or sometimes without heating. A molar ratio of the reagents CA: Phn (Bpy): lanthanide chloride: NaOH was equal to 3:1:1:3. The compound Eu(AcCHex)3·Phen was also synthesized by other method involving the preparation of an ethanol solution of a mixture of CA, Phen and EuCl3·6H2O in a molar ratio of 3:1:1 and adjusting the pH value of reaction mixture to 6 with a liquid ammonia. It should be pointed out that the heating of the reaction mixture results in a decrease in the keto/enol ratio of cycloalkanone [37] that promotes a binding of CA with the Ln3+ ion. At the same time, the probability of decomposition of cycloalkanonate anion increases.
 

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