Basic information
- CAS
4733-39-5- Standard SMILES
Cc1cc(-c2ccccc2)c2ccc3c(-c4ccccc4)cc(C)nc3c2n1- InChIKey
STTGYIUESPWXOW-UHFFFAOYSA-N- Molecular formula
- C26H20N2
- Average molar mass
- 360.4 g/mol
- Monoisotopic mass
- 360.16264865
Overview
reagent for copper; RN given refers to parent cpd
Names & identifiers
- Preferred name
- Bathocuproine
- IUPAC
- 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
- English name
- Bathocuproine
- Molecular formula
- C26H20N2
- Molecular weight
- 360.45
Names & synonyms
Bathocuproine4733-39-52,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline1,10-Phenanthroline, 2,9-dimethyl-4,7-diphenyl-9THP2V94FXDTXSID4063585NSC-89195RefChem:561106DTXCID9040556225-240-5BathocuproinMFCD00004972
Show more names
RMA-422BCP 157BLANC FIXE XRBathocuproineGrBathocuproin BCPEINECS 225-240-5BATHOCUPROINE AR
4,7-Diphenyl-2,9-dimethyl-1,10-phenanthrolineOprea1_173365STTGYIUESPWXOW-UHFFFAOYSA-2,7-diphenyl-1,10-phenanthroline1, 2,9-dimethyl-4,7-diphenyl-2,9-dimethyl-4,7-diphenylpyridino[3,2-h]quinoline2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline;Bathocuproin;2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline;2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline [BCP]NSC89195
Database identifiers
- CAS
4733-39-5- PubChem CID
- 65149
- DTXSID
DTXSID4063585- ChEMBL
CHEMBL220061- UNII
Properties
Computed structural properties
- XLogP
- 6.5
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 461
Experimental & physicochemical properties
PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
Physical DescriptionYellow powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 279 · 279-283 °C(lit.)
- Boiling point
- 482.47 °C · 482.47°C (rough estimate)
- Density
- 1.2408 · 1.2408 (rough estimate)
- refractive index
- 1.762 · 1.7620 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Benzene (Slightly, Heated), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
- form
- Powder
- pka
- 5.88 · 5.88±0.30(Predicted)
- color
- Yellow
- Water Solubility
- Soluble in methanol (36mg/100ml), ethanol, 2-propanol, bezene, and acetone. Partly miscible in water.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information1,10-Phenanthroline, 2,9-dimethyl-4,7-diphenyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS] See POLYCYCLIC AROMATIC HYDROCARBONS.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29339990
- risk_code
- 22-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 24/25-36-26-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY.
Uses & manufacturing
UsesUsed as a reagent for copper; [ChemIDplus]
General Manufacturing Information1,10-Phenanthroline, 2,9-dimethyl-4,7-diphenyl-: ACTIVE
Applications
DescriptionOrganic photovoltaic cells (OPVCs) are considered to be promising devices because of their mechanical flexibility, ease of fabrication and potential for low-cost production. For small-molecule OPVCs the most-common material to use between the acceptor, here C60, and the top electrode, Al, is 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, also known as bathocuproine. Indeed, the insertion of BCP results in an enhanced power-conversion efficiency (PCE). The improved power-conversion efficiency has been attributed to an increased exciton harvesting in the active layer. As BCP is a wide-band-gap material it acts as an exciton-blocking barrier (EBL) that prohibits excitons diffusing towards the Al electrode where they would otherwise be quenched.
UsesBathocuproine is used as a reagent for the determination of copper. It acts as an exciton blocking barrier which prohibits excitons diffusion process towards the Al electrode otherwise being quenched. It is the most commonly used buffer layer between acceptor and cathode layer.
Related reactions
53 records
Compound notes
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