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Rubrene

HCID 68203
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
517-51-1
Standard SMILES
c1ccc(-c2c3ccccc3c(-c3ccccc3)c3c(-c4ccccc4)c4ccccc4c(-c4ccccc4)c23)cc1
InChIKey
YYMBJDOZVAITBP-UHFFFAOYSA-N
Molecular formula
C42H28
Average molar mass
532.7 g/mol
Monoisotopic mass
532.2191009

Overview

chemiluminescent activator

Names & identifiers

Preferred name
Rubrene
IUPAC
5,6,11,12-tetraphenyltetracene
English name
Rubrene
Molecular formula
C42H28
Molecular weight
532.67

Names & synonyms

Rubrene517-51-15,6,11,12-TetraphenylnaphthaceneRubrenNaphthacene, 5,6,11,12-tetraphenyl-DTXSID8060161RefChem:180238DTXCID6041058208-242-05,6,11,12-TetraphenyltetracenerubreneperoxideMFCD00003703
Show more names
RubrueneRubrene,99%RUBRENE, 98%+Rubrene ,98.5%RUBRENE, POWDERRubrene, 99% 1GR
5,11,12-TetraphenylnaphthaceneNaphthacene,6,11,12-tetraphenyl-CS-0110891Rubrene; (5,6,11,12-Tetraphenylnaphthacene)5,6,11,12-tetraphenyl-naphthacene, (rubrene)Q415911Rubrene, sublimed grade, 99.99% trace metals basisC42H28

Database identifiers

CAS
517-51-1
PubChem CID
68203
DTXSID
DTXSID8060161
EC Number
208-242-0
Nikkaji
J6.576E

Properties

Computed structural properties

XLogP
12.2
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
4
Heavy atoms
42
Formal charge
0
Complexity
696

Experimental & physicochemical properties

PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials PropertiesAngular frequency
Physical DescriptionDark brown or red powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
330 · 330-335 °C (lit.)
Boiling point
315 °C · >315°C
Density
1.175 · 1.1750 (estimate)
refractive index
1.716 · 1.7160 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
THF: solublechloroform: solubletoluene: soluble
form
powder
color
Red
optical activity
[α]/D
Water Solubility
Soluble in hot toluene. Insoluble in water.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS] See POLYCYCLIC AROMATIC HYDROCARBONS.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

F
10-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29029090
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H335-H315-H319
Precautionary statements
P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362

Chemistry & industry

Uses & manufacturing

UsesChemiluminescent activator. [ChemIDplus]
General Manufacturing InformationNaphthacene, 5,6,11,12-tetraphenyl-: ACTIVE
Applications · 3 items

DescriptionRubrene, a molecule with a tetracene backbone and four appended phenyl rings, is one of the most studied molecular semiconductors due to its high charge mobility. Notably, room-temperature hole mobilities of the order of 20-40 cm2V-1s-1 have been measured for rubrene in single-crystal organic field-effect transistors (SC-OFET). It is widely used in organic electronics, especially organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs).

UsesRubrene is an organic semiconductor used in organic light-emitting diodes (OLEDs) and organic field-effect transistors. It is used as a sensitizer in chemoluminesence. It is also used to prepare single crystal transistors. It acts as a reagent for chemiluminescence research and for transition metal complex ligation. Further, it is used as a p-type organic semiconductor.

General DescriptionRubrene is a tetraphenyl derivative of tetracene that is used as an organic semiconductor. It is used as a source material in the fabrication of rubrene single crystal based transistors with carrier mobility over 10 cm2V1s1.

Preparation methods · 1 item

PreparationRubrene is an organic molecule that has long been known for its outstanding semiconductor performance in organic electronic devices.Rubrene is prepared by treating 1,1,3-triphenylprop-2-yne-1-ol with thionyl chloride.The resulting chloroallene undergoes dimerization and dehydrochlorination to give rubrene.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Sensitive
Air Sensitive
λmax
299 nm460 · 299 nm460 nm (2nd)
BRN
1917339 · 1917339
InChI
1S/C42H28/c1-5-17-29(18-6-1)37-33-25-13-14-26-34(33)39(31-21-9-3-10-22-31)42-40(32-23-11-4-12-24-32)36-28-16-15-27-35(36)38(41(37)42)30-19-7-2-8-20-30/h1-28H
InChIKey
YYMBJDOZVAITBP-UHFFFAOYSA-N
SMILES
c1ccc(cc1)-c2c3ccccc3c(-c4ccccc4)c5c(-c6ccccc6)c7ccccc7c(-c8ccccc8)c25
CAS DataBase Reference
517 · 517-51-1(CAS DataBase Reference)
NIST Chemistry Reference
5 · 5,6,11,12-Tetraphenylnaphthacene(517-51-1)
EPA Substance Registry System
5 · Naphthacene, 5,6,11,12-tetraphenyl- (517-51-1)
Absorption
299 nm · λmax299 nm (in THF)
UNSPSC Code
12352103 · 12352103
NACRES
23 · NA.23
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
335 · H335-H315-H319
Precautionary statements
264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
F
10 · 10-23
TSCA
TSCA listed
HS Code
29029090 · 29029090
Storage Class
11 · 11 - Combustible Solids