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Merck

N1501

Sigma-Aldrich

Neocuproine

≥98%

Sinónimos:

2,9-Dimethyl-1,10-phenanthroline, DMPHEN

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About This Item

Fórmula empírica (notación de Hill):
C14H12N2
Número de CAS:
Peso molecular:
208.26
Número CE:
Número MDL:
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
NACRES:
NA.22
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Ensayo

≥98%

Formulario

crystalline

color

white to beige

cadena SMILES

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

Clave InChI

IYRGXJIJGHOCFS-UHFFFAOYSA-N

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Descripción general

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.[1]

Aplicación

Neocuproine can be used as a ligand in the:
  • Preparation of fluorinated metal-organic frameworks (F-MOFs).[2]
  • Regioselective C-H arylation of indoles with phenylboronic acids through an oxidative boron Heck reaction.[3]
  • Allylation reaction of aldehydes with allylboronates in the presence of Zn(OH)2 as a catalyst.[4]
  • Iridium-catalyzed silylation of five-membered heteroarenes to synthesize silylarenes.[5]

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Assem Barakat et al.
International journal of molecular sciences, 14(12), 23941-23954 (2013-12-20)
[NiCl2(C14H12N2)(H2O)] complex has been synthesized from nickel chloride hexahydrate (NiCl2·6H2O) and 2,9-dimethyl-1,10-phenanthroline (dmphen) as N,N-bidentate ligand. The synthesized complex was characterized by elemental analysis, infrared (IR) spectroscopy, ultraviolet-visible (UV-vis) spectroscopy and differential thermal/thermogravimetric analysis (TG/DTA). The complex was further confirmed
Shū Kobayashi et al.
Chemistry, an Asian journal, 8(9), 2033-2045 (2013-06-19)
Zn(OH)2-catalyzed allylation reactions of aldehydes with allylboronates in aqueous media have been developed. In contrast to conventional allylboration reactions of aldehydes in organic solvents, the α-addition products were obtained exclusively. A catalytic cycle in which the allylzinc species was generated
Yan Wang et al.
Journal of the American Society for Mass Spectrometry, 19(9), 1353-1360 (2008-07-19)
S-nitrosylation of proteins serves an important role in regulating diverse cellular processes including signal transduction, DNA repair, and neurotransmission. Identification of S-nitrosylation sites is crucial for understanding the significance of this post-translational modification (PTM) in modulating the function of a
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Analytical chemistry, 82(10), 4252-4258 (2010-04-27)
A low-cost optical sensor using an immobilized chromogenic redox reagent was devised for measuring the total antioxidant level in a liquid sample without requiring sample pretreatment. The reagent, copper(II)-neocuproine (Cu(II)-Nc) complex, was immobilized onto a cation-exchanger film of Nafion, and
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We and others recently identified copper resistance as important for virulence of Mycobacterium tuberculosis. Here, we introduce a high-throughput screening assay for agents that induce a copper hypersensitivity phenotype in M. tuberculosis and demonstrate that such copper-boosting compounds are effective

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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