Basic information
- Standard SMILES
c1ccc2cc3cc4cc5ccccc5cc4cc3cc2c1- InChIKey
SLIUAWYAILUBJU-UHFFFAOYSA-N- Molecular formula
- C22H14
- Average molar mass
- 278.3 g/mol
- Monoisotopic mass
- 278.10955045
Overview
Pentacene is an acene that consists of five ortho-fused benzene rings in a rectilinear arrangement. It is an acene and a member of pentacenes.
Names & identifiers
- Preferred name
- Pentacene
- IUPAC
- pentacene
- English name
- Pentacene
- Molecular formula
- C22H14
- Molecular weight
- 278.35
Names & synonyms
Show more names
Database identifiers
- CAS
135-48-8- PubChem CID
- 8671
- DTXSID
DTXSID7059648- ChEBI
CHEBI:33148- UNII
- 9FQU5HA0UY
- EC Number
- 205-193-7
- Nikkaji
- J3.682.356I、J5.604I
Properties
Computed structural properties
- XLogP
- 6.7
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 325
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 372 · 372-374 °C (subl.)
- Boiling point
- 356.16 °C · 356.16°C (rough estimate)
- Density
- 1.1489 · 1.1489 (estimate)
- refractive index
- 1.812 · 1.8120 (estimate)
- storage temp.
- 0 · 0-6°C
- solubility
- Soluble in organic solvents.
- form
- Fine Crystalline Powder
- color
- Dark blue, purple, or black
- Water Solubility
- insoluble
- semiconductor properties
- P-type (mobility=0.4-3cm2/V·s) (on/off ratio=1E5-1E8)
- Sensitive
- Air & Light Sensitive
- λmax
- 577 nm · 577nm(Toluene)(lit.)
- Merck
- 14 · 14,7107
- BRN
- 1912418 · 1912418
- Stability
- Stable, but air and light sensitive. Incompatible with strong oxidizing agents.
- InChI
- 1S/C22H14/c1-2-6-16-10-20-14-22-12-18-8-4-3-7-17(18)11-21(22)13-19(20)9-15(16)5-1/h1-14H
- InChIKey
- SLIUAWYAILUBJU-UHFFFAOYSA-N
- SMILES
- c1ccc2cc3cc4cc5ccccc5cc4cc3cc2c1
- CAS DataBase Reference
- 135 · 135-48-8(CAS DataBase Reference)
- FDA UNII
- 9 FQU5HA0UY · 9FQU5HA0UY
- NIST Chemistry Reference
- Pentacene(135-48-8)
- EPA Substance Registry System
- Pentacene (135-48-8)
- Absorption
- 576 nm · λmax= 576 nm (in benzene) [11]
- Solvent
- 60 · Pentacene is insoluble in most of the organic solvents. Trichlorobenzene is normally used to form solution at 60 - 120°C [10]
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 32 · NA.32
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Danger
- Hazard statements
- 225 · H225
- Precautionary statements
- 501 · P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- F
- 8 · 8-10-23
- TSCA
- TSCA listed
- HS Code
- 29029090 · 29029090
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Hazard information
Toxicology
Toxicity Summary
The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)
Safety data
- F
- 8-10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29029090
- Signal word
- Danger
- Symbol(GHS)
- GHS02
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H225
- Precautionary statements
- P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235
Chemistry & industry
Pharmacology
Metabolism/Metabolites
PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)
Uses & manufacturing
Uses
Proposed use as a photoconductor (instead of selenium) in copying systems; [Hawley]
PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)
Applications
DescriptionPentacene, an acene with flat-like molecules made of five linearly-fused benzene rings, has been extensivelystudied as a p-type semiconductor in organic field-effecttransistors. It is known to exhibit large carrier mobilitiesof about 1 cm2 /V s within the plane parallel to thesubstrate.
UsesPentacene can be used as OPV device (Organo Photovoltaic) and as semiconductors.
UsesPentacene is a polycyclic aromatic compound found in wastewater treatment facility units.
General DescriptionTGA/DSC Lot specific traces available upon request
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: An acene that consists of five ortho-fused benzene rings in a rectilinear arrangement.
Related reactions
Linked notes
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