Naphthacene

HCID 7080CAS 92-24-0

Basic information

Standard SMILES
c1ccc2cc3cc4ccccc4cc3cc2c1
InChIKey
IFLREYGFSNHWGE-UHFFFAOYSA-N
Molecular formula
C18H12
Average molar mass
228.3 g/mol
Monoisotopic mass
228.09390038

Names & identifiers

Preferred name
Naphthacene
IUPAC
tetracene
English name
NAPHTHACENE
Molecular formula
C18H12
Molecular weight
228.29

Names & synonyms

NaphthaceneTETRACENE92-24-02,3-BenzanthraceneBenz[b]anthraceneChrysogenRubeneBenz(b)anthracene2,3-BenzanthreneQYJ5Z6712RDTXSID4059045CHEBI:32600
Show more names
TetracenMethaceneNAPHTHYCENETetrabenzeneNaphthacene>
RefChem:164592DTXCID6048751202-138-9MFCD00003702EINECS 202-138-9UNII-QYJ5Z6712RNaphthacene (>80%)NAPHTHACENE [MI]

Database identifiers

CAS
92-24-0
PubChem CID
7080
DTXSID
DTXSID4059045
ChEMBL
CHEMBL1797272
ChEBI
CHEBI:32600
UNII
QYJ5Z6712R
EC Number
202-138-9
Nikkaji
J1.536.811J、J4.651E

Properties

Computed structural properties

XLogP
5.9
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
18

Experimental & physicochemical properties

Melting Point357 °C. [ChemIDplus]
Physical Description"Orange leaflets from xylene"; melting point = 341 degrees C; [Merck Index] Has slight green fluorescence in daylight; [Hawley]
Kovats Retention Index · 2 items

2395;2425;2436;2386;405.7;403.9;405;403.9

2426;2425;403.5;403.15;402.86;407.3;401.28;403.52;403.51;403.7;403.89;408.3;408.3

Physicochemical properties

Melting point
300 °C · >300 °C(lit.)
Boiling point
305.1 °C · 305.1°C (rough estimate)
Density
1.35 · 1.35
refractive index
1.55 · 1.5500 (estimate)
form
Crystalline Powder
color
Orange

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (20%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (20%): Harmful in contact with skin [Warning Acute toxicity, dermal];H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation];H400 (80%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (80%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationChemical: Naphthacene
Hazards SummaryAn eye, skin, and respiratory tract irritant; May be harmful if swallowed, inhaled or absorbed through the skin; [MSDSonline] May explode if shocked; [Hawley] See POLYCYCLIC AROMATIC HYDROCARBONS.
Hazard Classes and CategoriesAcute Tox. 4 (20%);Acute Tox. 4 (20%);Acute Tox. 4 (20%);Aquatic Acute 1 (80%);Aquatic Chronic 1 (80%)

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 related PAHs (L2154).

Regulatory information

Regulatory InformationChemical: Naphthacene

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
QI7605000
ridadr
UN 3077 9/PG 3
hs_code
29029090

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

Present in coal tar and contaminates commercial anthracene; [Merck Index] Used in organic synthesis; [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 InformationNaphthacene: ACTIVE
Applications · 3 items

Usesp-Type organic conductor and OLED dopant. Sublimed grade for organic electronic device applications.

UsesNaphthacene is a polycyclic aromatic hydrocarbon. Naphthacene is often used as a molecular organic semiconductor in organic field-effect transistors and organic light-emitting diodes. Naphthacene is also used in various applications involving the enhancement of photocurrent.

General DescriptionBenz[b]anthracene is an ethylnylated acene that is a conducting polymer, which can be used as a donor material. It has a high photoluminescence and quantum yield that makes it a promising candidate in the development of single crystal electronic material.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
杭州奥得科技有限公司0571-88772972-0 15057128248 · [email protected]

Additional notes

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

Related reactions

11 records

Linked notes

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