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
Show more names
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
- Formal charge
- 0
- Complexity
- 236
Experimental & physicochemical properties
Kovats Retention Index
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
- Water Solubility
- 1.507 ug/L · 1.507ug/L(25 ºC)
- semiconductor properties
- P-type (mobility=0.4cm2/V·s)
- λmax
- 277 nm · 277 nm
- Merck
- 14 · 14,6369
- BRN
- 1909299 · 1909299
- Henry's Law Constant
- 2 · 2.0×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Stability
- Stable. Incompatible with strong oxidizing agents.
- InChI
- InChI=1S/C18H12/c1-2-6-14-10-18-12-16-8-4-3-7-15(16)11-17(18)9-13(14)5-1/h1-12H
- InChIKey
- IFLREYGFSNHWGE-UHFFFAOYSA-N
- SMILES
- C1=C2C(C=C3C(=C2)C=C2C(C=CC=C2)=C3)=CC=C1
- CAS DataBase Reference
- 92 · 92-24-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 5 Z6712R · QYJ5Z6712R
- EPA Substance Registry System
- Naphthacene (92-24-0)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 271 · P271-P261-P280
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xn,N
- Risk Statements
- 40 · 40-50/53
- Safety Statements
- 45 · 45-36/37-61-60-24/25
- RIDADR
- 3077 · UN 3077 9/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 7605000 · QI7605000
- TSCA
- TSCA listed
- HS Code
- 29029090 · 29029090
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
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
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)
Regulatory information
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- QI7605000
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29029090
- risk_code
- 40-50/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,N
- safety_code
- 45-36/37-61-60-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P271-P261-P280
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
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)
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: An acene that consists of four ortho-fused benzene rings in a rectilinear arrangement.
Related reactions
Linked notes
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