Basic information
- CAS
123333-55-1- Standard SMILES
c1cc(-c2ccncc2)ccn1- InChIKey
MWVTWFVJZLCBMC-UHFFFAOYSA-N- Molecular formula
- C10H8N2
- Average molar mass
- 156.18 g/mol
- Monoisotopic mass
- 156.06874826
Overview
4,4'-bipyridine is a bipyridine in which the two pyridine moieties are linked by a bond between positions C-4 and C-4'.
Names & identifiers
- Preferred name
- 4,4'-Bipyridine
- IUPAC
- 4-pyridin-4-ylpyridine
- English name
- 4,4'-Bipyridine
- Molecular formula
- C10H8N2
- Molecular weight
- 156.18
Names & synonyms
4,4'-Bipyridine553-26-44,4'-DIPYRIDYL4,4'-Bipyridyl4-(4-Pyridyl)pyridine4,4'-Dipyridinegamma,gamma'-Bipyridylgamma,gamma'-DipyridylDTXSID2027200X4O2OD61CBNSC-404423DTXCID107200
Show more names
4,4-BIPYRIDINE4'-Bipyridine4,4''-BipyridineGAMMA,GAMMA-DIPYRIDYL'LGC' (1608)
CHEBI:30985RefChem:506524209-036-3628-542-94,4-Bipyridyl4-pyridin-4-ylpyridine4,4-Dipyridyl4,4'-Dipyridyl hydrate
Database identifiers
- CAS
123333-55-1、37275-48-2、553-26-4- PubChem CID
- 11107
- DTXSID
DTXSID2027200- ChEMBL
CHEMBL1374568- ChEBI
CHEBI:30985- UNII
- X4O2OD61CB
- EC Number
- 209-036-3、628-542-9
- Nikkaji
- J45.972K
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 108
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Pyridines
SpringerMaterials PropertiesSchoenflies notation
LogP1.33
Vapor Pressure0.0000556 [mmHg]
Physical DescriptionSolid; [IUCLID] White crystalline solid with a pungent odor; [Alfa Aesar MSDS]
Collision Cross Section135.5 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID2027200]
Physicochemical properties
- Melting point
- 109 · 109-112 °C(lit.)
- Boiling point
- 305 °C · 305 °C(lit.)
- Density
- 1.2814 · 1.2814 (rough estimate)
- refractive index
- 1.6057 · 1.6057 (estimate)
- Flash point
- 304 · 304-305°C
Safety & regulation
GHS classification
GHS Classification
Danger
H301+H311 (35.4%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]
P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 79 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory Information
Chemical: 4,4'-Bipyridine
SP - indicates a substance that is identified in a proposed Significant New Use Rule.
4,4'-Bipyridine: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Skin lesions of the face, neck, and arms reported in 30 employees in a manufacturing plant; Histological evaluation revealed a progression from keratosis to Bowen's disease, and squamous cell carcinoma in 6 cases; A study of 246 employees at 28 factories during 1984-1985 showed 34% with hyperpigmented macules and 20% with marked hyperkeratotic lesions; Not irritating to rabbit skin; Not sensitizing in guinea pig maximization test; Changes in the lung, some changes in kidney and spleen, lachrymation, swelling around eyes, and occasional convulsions observed in oral lethal-dose studies of rats; Histopathological changes to liver and kidney reported in skin irritation study of rats; Dermal LD50 (rabbit) = 400-800 mg/kg; [IUCLID] Causes lacrimation, somnolence, and dyspnea in oral lethal-dose studies of rats; [RTECS] Generally not irritating to skin; Toxic by ingestion and skin absorption; [Alfa Aesar MSDS] See 2,3'-Bipyridine and 2,2'-Bipyridine.
Hazard Classes and Categories
Acute Tox. 3 (98.7%)
Chemistry & industry
Uses & manufacturing
Uses
Formed as a pyrolysis product in tobacco smoke and also from the degradation of the herbicide paraquat; [Reference #1]
Smoking cigarettes [Category: Food & Drugs]
General Manufacturing Information4,4'-Bipyridine: ACTIVE
Applications
Uses4,4'-Bipyridine is used in transition-metal complex catalyst chemistry for uniform polymerization, in luminescence chemistry and in spectrophotometric analysis. It plays an important role as a photosensitizer and luminescent material. It is also used as a precursor to paraquat viz. N,N'-dimethyl-4,4'-bipyridinium.
General Description4,4′-Dipyridyl (BPY) is an organic linker mainly used in the preparation of coordination polymers. It is a pyridine derivative in which pyridyl groups can rotate along the carbon-carbon structure. It can be used as a catalyst for photoelectrochemical reduction.
Upstream & downstream products
Upstream raw materials
Related reactions
27 records
Compound notes
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