Basic information
- Standard SMILES
c1ccc2c(c1)c1ccccc1c1ccccc21- InChIKey
SLGBZMMZGDRARJ-UHFFFAOYSA-N- Molecular formula
- C18H12
- Average molar mass
- 228.3 g/mol
- Monoisotopic mass
- 228.09390038
Overview
Triphenylene is an ortho-fused polycyclic arene consisting of four fused benzene rings.
Names & identifiers
- Preferred name
- Triphenylene
- IUPAC
- triphenylene
- English name
- Triphenylene
- Molecular formula
- C18H12
- Molecular weight
- 228.29
Names & synonyms
TRIPHENYLENE217-59-49,10-BenzophenanthreneIsochrysene9,10-BenzphenanthreneBenzo(l)phenanthreneBenzo[l]phenanthrene1,2,3,4-DibenznaphthaleneDTXSID9059757NSC-5745518WX3373I0CHEBI:33080
Show more names
Triphenylene,98%benzo(1)phenanthreneriphenyleneTriphenylene 98%Triphenylene >benzo(l)phenathrene
RefChem:191904DTXCID7036537205-922-9MFCD00001108triphenylene (purity)1,2:3,4-Dibenznaphthalene53814-75-8triphenylen
Database identifiers
- CAS
217-59-4- PubChem CID
- 9170
- DTXSID
DTXSID9059757- ChEMBL
CHEMBL1797416- ChEBI
CHEBI:33080- UNII
- 18WX3373I0
- EC Number
- 205-922-9
- Nikkaji
- J6.134D
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 217
Experimental & physicochemical properties
PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP5.84
Physical DescriptionLight yellow powder, insoluble in water; [MSDSonline]
Collision Cross Section143.6 Ų [M*]+
Physicochemical properties
- Melting point
- 195 · 195-198 °C(lit.)
- Boiling point
- 438 °C · 438 °C(lit.)
- Density
- 1.302 · 1.302
- refractive index
- 1.55 · 1.5500 (estimate)
- Flash point
- 438 °C · 438°C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Soluble in ethanol, benzene, acetic acid, oils and chloroform.
- form
- Crystalline Needles
- color
- White to beige
- Water Solubility
- 6.6 ug/L · 6.6ug/L(25.00 ºC)
- λmax
- 335 nm · 335nm(Hexane)(lit.)
- Merck
- 14 · 14,9740
- BRN
- 1342908 · 1342908
- Henry's Law Constant
- 6.4 · 6.4×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Major Application
- environmental
- InChI
- 1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
- InChIKey
- SLGBZMMZGDRARJ-UHFFFAOYSA-N
- SMILES
- c1ccc2c(c1)c3ccccc3c4ccccc24
- CAS DataBase Reference
- 217 · 217-59-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 18 WX3373I0 · 18WX3373I0
- NIST Chemistry Reference
- Triphenylene(217-59-4)
- IARC
- 3 · 3 (Vol. Sup 7, 92) 2010
- EPA Substance Registry System
- Triphenylene (217-59-4)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS09
- Signal word
- Danger
- Hazard statements
- 318 · H318-H410
- Precautionary statements
- 273 · P273-P280-P305+P351+P338-P391-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,N
- Risk Statements
- 41 · 41-50/53
- Safety Statements
- 22 · 22-24/25-61-60-39-26
- RIDADR
- 3077 · UN 3077 9/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 2925000 · YK2925000
- HazardClass
- 9 · 9
- PackingGroup
- Ⅲ
- HS Code
- 29029090 · 29029090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
Hazard information
Hazards SummaryAn irritant; [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
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 Classification
Triphenylene
Group 3: Not classifiable as to its carcinogenicity to humans
Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)
2010
2005
3, not classifiable as to its carcinogenicity to humans. (L135)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- YK2925000
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29029090
- risk_code
- 41-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS09
- hazard_code
- Xi,N
- safety_code
- 22-24/25-61-60-39-26
- hazard_class
- 9
- Storage Class
- 11 - Combustible Solids
- packing_group
- Ⅲ
- Hazard statements
- H318-H410
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1
- Precautionary statements
- P273-P280-P305+P351+P338-P391-P501
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
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
UsesTriphenylene is a polycyclic aromatic hydrocarbon (PAH) that can be isolated from coal tar. Triphenylene emits fluorescence in the ultraviolet region and is a useful compound for developing semiconductor devices.
General DescriptionTriphenylene belongs to the class of polycyclic aromatic hydrocarbons, which is commonly employed as a substrate for use as a precursor for the synthesis of graphenes, carbon nanotubes, buckminsterfullerenes as well as polycyclic heteroaromatics.
Preparation methods
PreparationTriphenylene synthesis: 2-Chlorobenzoic acid(78mg, 0.5mmol), iodonium salt (236mg, 0.55mmol), palladium acetate (2.8mg, 0.0125mmol), potassium carbonate (152mg, 1.1mmol) were dissolved in 3mL of NMP solvent was heated to 110 °C and stirred for 17 hours, cooled to room temperature, extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated, and subjected to column chromatography to obtain 92 mg of triphenylene as a white solid, The yield was 80%.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Triphenylene is an ortho-fused polycyclic arene consisting of four fused benzene rings.
Related reactions
10 records
Linked notes
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