Pentacene

HCID 8671CAS 135-48-8

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

PENTACENE135-48-8lin-Dibenzanthracenelin-NaphthoanthraceneBenzo[b]naphthacene2,3:6,7-DibenzanthraceneBenzo(b)naphthacene9FQU5HA0UYNSC-90784DTXSID7059648CHEBI:33148RefChem:171296
Show more names
entacenePentacene 99%Pentacene,98%Pentacene (crude)PENTACENE REFINEDPENTACENE, SUBLIMEDPENT-2-ENEDIOICACID
DTXCID4034281205-193-7UNII-9FQU5HA0UYMFCD00003710NSC 90784Pentacene (purified by sublimation)Pentacene, (purified by sublimation)AKOS015840937

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

Experimental & physicochemical properties

PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials PropertiesAngular frequency
LogP7.11
Physical DescriptionDeep blue solid with violet luster; [Merck Index]

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.

Safety & regulation

Hazard information

Hazards SummaryMay cause irritation; [MSDSonline] See POLYCYCLIC AROMATIC HYDROCARBONS.

Toxicology

TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
Exposure RoutesOral (L10) ; inhalation (L10)
Toxicity Summary · 1 item

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)

Signs and SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
Carcinogen ClassificationNot listed by IARC. IARC has evaluated other PAHs (L2154).

Safety data

F
8-10-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29029090
Signal word
Danger

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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 · 2 items

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)

General Manufacturing InformationPentacene: ACTIVE
Applications · 4 items

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

Additional notes

DefinitionChEBI: An acene that consists of five ortho-fused benzene rings in a rectilinear arrangement.

Related reactions

9 records

Linked notes

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