5,6-Diamino-1,10-phenanthroline

• CAS: 168646-54-6
• Catalog Number: ACM168646546-2
• Category: Main Products
• Molecular Weight: 210.23
• Molecular Formula: C12H10N4
• Synonyms: 1,10-Phenanthroline-5,6-diamine
• IUPAC Name: 1,10-phenanthroline-5,6-diamine
• InChI: MNXMBMNXSPNINS-UHFFFAOYSA-N
• InChI Key: InChI=1S/C12H10N4/c13-9-7-3-1-5-15-11(7)12-8(10(9)14)4-2-6-16-12/h1-6H,13-14H2
• Boiling Point: 155-156 °C
• Melting Point: 155-156 °C
• Appearance: Orange powder
• Isomeric SMILES: C1=CC2=C(C(=C3C=CC=NC3=C2N=C1)N)N

Case Study

5,6-Diamino-1,10-Phenanthroline for the Synthesis of Copper(I)-Diimine-Diphosphine Complexes

Yao, Xi-Xi, et al. Polyhedron, 2015, 92, 84-92.

The chemical interaction between 5,6-diamino-1,10-phenanthroline (dap) and diphosphine ligands xantphos [9,9-dimethyl-4,5-bis(diphenylphosphino)-9H-xanthene (xantphos)] or bis[(2-diphenylphosphino)phenyl] ether (POP) with [Cu(MeCN)4]ClO4 resulted in the synthesis of mononuclear complex [Cu(dap)(PP)]ClO4 (2a) and binuclear complexes [Cu2(μ-pdi)(PP)2](ClO4)2 (2b) and [Cu2(μ-ttpd)(xantphos)2](ClO4)2 (1c).
Synthetic routes of the Cu(I) complexes
· The synthetic procedure for these Cu(I) complexes began with the reaction of 5,6-diamino-1,10-phenanthroline (dap), xantphos or POP, and Cu(CH3CN)4ClO4 in a 1: Mononuclear complexes 1a or 2a form when the reaction between 5,6-diamino-1,10-phenanthroline (dap), xantphos or POP and Cu(CH3CN)4ClO4 occurs at a 1:1:1 stoichiometric ratio under conditions lacking moisture and oxygen.
· Experiments demonstrated that complexes 1a and 2a can form even when exposed to oxygen. Increasing the stoichiometric ratio to 1: The formation of binuclear complexes 1b and 2b with pdi occurred when the mixture at a 1:2:2 ratio crystallized through air diffusion.
· Additionally, combining dap, xantphos, and Cu(CH3CN)4ClO4 in a 1: The combination of dap and xantphos plus Cu(CH3CN)4ClO4 in a 2:2 ratio with a dap solution under aerobic conditions through diffusion crystallization produced complex 1c and complex 1b.

5,6-Diamino-1,10-Phenanthroline Surface Functionalized Carbon Black for Oxygen Reduction Catalyst Preparation

Pauric, Allen D., et al. ECS Transactions, 2010, 28(23), 55.

A non-precious metal catalyst (NPMC) for oxygen reduction reaction was prepared by surface modification of carbon black (Black Pearls 2000, BP) with 5,6-diamino-1,10-phenanthroline (aphen) via diazo and benzimidazole coupling chemistry. The prepared catalysts were highly active for oxygen reduction reaction (ORR) by introduction of Fe and pyrolysis at 700°C in NH3/N2 atmosphere.
· Diazonium Coupling Method
200 mg of BP was mixed with 25 mg of aphen (1 equivalent), along with 4 equivalents of concentrated sulfuric acid and 2 equivalents of sodium nitrite. This reaction converts the amino groups of aphen into diazonium groups, which then interact with the carbon surface. After stirring the mixture at room temperature for 30 minutes, collected the modified carbon through suction filtration before washing it with water and drying it overnight at 100 °C then grinding it into a fine powder. This product will be referred to as BP-D.
· Benzimidazole Coupling Method
In a separate procedure, 25 mg of aphen and 100 mg of BP were dissolved in 25 mL of 4M HCl and refluxed for 24 hours. The resulting sample was collected via suction filtration, washed with water, acetone, and methanol, dried overnight at 100 °C, and then ground to a fine powder. This product will be referred to as BP-B.

Custom Q&A

What is the molecular formula of 5,6-diamino-1,10-phenanthroline?

The molecular formula is C12H10N4.

What are the synonyms of 5,6-diamino-1,10-phenanthroline?

The synonyms are 168646-54-6, 1,10-phenanthroline-5,6-diamine, MFCD12913573, and YSWG187.

What is the molecular weight of 5,6-diamino-1,10-phenanthroline?

The molecular weight is 210.23 g/mol.

When was 5,6-diamino-1,10-phenanthroline created?

It was created on October 26, 2006.

When was 5,6-diamino-1,10-phenanthroline last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of 5,6-diamino-1,10-phenanthroline?

The IUPAC name is 1,10-phenanthroline-5,6-diamine.

What is the InChI of 5,6-diamino-1,10-phenanthroline?

The InChI is InChI=1S/C12H10N4/c13-9-7-3-1-5-15-11(7)12-8(10(9)14)4-2-6-16-12/h1-6H,13-14H2.

What is the InChIKey of 5,6-diamino-1,10-phenanthroline?

The InChIKey is MNXMBMNXSPNINS-UHFFFAOYSA-N.

What is the canonical SMILES of 5,6-diamino-1,10-phenanthroline?

The canonical SMILES is C1=CC2=C(C(=C3C=CC=NC3=C2N=C1)N)N.

What is the CAS number of 5,6-diamino-1,10-phenanthroline?

The CAS number is 168646-54-6.