Basic information
- CAS
27318-90-7- Standard SMILES
O=C1C(=O)c2cccnc2-c2ncccc21- InChIKey
KCALAFIVPCAXJI-UHFFFAOYSA-N- Molecular formula
- C12H6N2O2
- Average molar mass
- 210.19 g/mol
- Monoisotopic mass
- 210.04292743
Overview
1,10-Phenanthroline-5,6-dione is a member of phenanthrolines.
Names & identifiers
- Preferred name
- 1,10-Phenanthroline-5,6-dione
- IUPAC
- 1,10-phenanthroline-5,6-dione
- English name
- 1 10-PHENANTHROLINE-5 6-DIONE 97
- Molecular formula
- C12H6N2O2
- Molecular weight
- 210.19
Names & synonyms
1,10-Phenanthroline-5,6-dione27318-90-7phendioneLDN-737948JD7KXA2W01,10-PadNSC-346882DTXSID60181763phen-dioneRefChem:410366DTXCID00104254627-684-9
Show more names
11,10-Phenanthroline-5,6-dione, 98%phen-5,6-dionePhenanthroline-5,6-dipyridobenzoquinoneStahl phd oxidant phd1,10-Phenthroline-5,6-dione1,10-Phenanthrolin-5,6-dione
MFCD00014473Stahl phd oxidant5,6-dihydro-1,10-phenanthroline-5,6-dioneMLS0031710481,10-phenanthroline-5,6-quinone1 10-PHENANTHROLINE-5 6-DIONE 97NSC346882NSC 346882
Database identifiers
- CAS
27318-90-7- PubChem CID
- 72810
- DTXSID
DTXSID60181763- ChEMBL
CHEMBL235504- ChEBI
CHEBI:231244- UNII
- 8JD7KXA2W0
- EC Number
- 627-684-9
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 59.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 297
Physicochemical properties
- Melting point
- 260 °C · 260 °C (dec.)(lit.)
- Boiling point
- 456.1 · 456.1±20.0 °C(Predicted)
- Density
- 1.444 · 1.444±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- form
- powder to crystal
- pka
- 0.26 · 0.26±0.20(Predicted)
- color
- Light yellow to Amber to Dark green
- Water Solubility
- Insoluble in water.
- λmax
- 251 nm · 251nm(MeOH)(lit.)
- InChI
- InChI=1S/C12H6N2O2/c15-11-7-3-1-5-13-9(7)10-8(12(11)16)4-2-6-14-10/h1-6H
- InChIKey
- KCALAFIVPCAXJI-UHFFFAOYSA-N
- SMILES
- N1C2=C(C(=O)C(=O)C3=C2N=CC=C3)C=CC=1
- FDA UNII
- 8 JD7KXA2W0 · 8JD7KXA2W0
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 86 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29349990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
Uses1,10-Phenanthroline-5,6-dione is a Bifunctional quinone oxidant which, when used in conjunction with Zn2+ catalysts, is used to affect the aerobic oxidation of secondary amines to a variety of value added motifs, including indoles.
General Description1,10-Phenanthroline-5,6-dione (phendio) forms Cu(II) and Ag(I) phendio complexes, which show potent anti-fungal and anti-cancer activity. The modification of glassy carbon (GC) electrodes with phendio complexes of transition metals leads to the catalytic oxidation of NADH at low overpotential.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
280 records
HRID 1317105As catalystHigh-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
Compound notes
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