N1501

Neocuproine

≥98%

• Synonym(s): 2,9-Dimethyl-1,10-phenanthroline, DMPHEN
• Empirical Formula (Hill Notation): C₁₄H₁₂N₂
• CAS Number: 484-11-7
• Molecular Weight: 208.26
• EC Number: 207-601-9
• MDL number: MFCD00004973
• UNSPSC Code: 12352100
• PubChem Substance ID: 57654439
• NACRES: NA.22

Properties

• Quality Level: 200
• Assay: ≥98%
• form: crystalline
• color: white to beige
• SMILES string: Cc1ccc2ccc3ccc(C)nc3c2n1
• InChI: 1S/C14H12N2/c1-9-3-5-11-7-8-12-6-4-10(2)16-14(12)13(11)15-9/h3-8H,1-2H3
• InChI key: IYRGXJIJGHOCFS-UHFFFAOYSA-N

Description

General description

Neocuproine is a heterocyclic organic compoundcommonly utilized as a chelating agent in various transition metal-catalyzedreactions. These include alcohol oxidation, oxidative cleavage of carbon-carbonbonds, C-C bond forming coupling reactions, allylation of carbonyls, alkylzincalkynylations, nickel-mediated decarbonylative cross-couplings,Buchwald–Hartwig-type couplings, and allylic substitution reactions.

Application

Neocuproine can be used as a ligand in the:

• Preparation of fluorinated metal-organic frameworks (F-MOFs).
• Regioselective C-H arylation of indoles with phenylboronic acids through an oxidative boron Heck reaction.
• Allylation reaction of aldehydes with allylboronates in the presence of Zn(OH)₂ as a catalyst.
• Iridium-catalyzed silylation of five-membered heteroarenes to synthesize silylarenes.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves