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CAS No.: | 217-59-4 |
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Name: | Triphenylene |
Article Data: | 201 |
Molecular Structure: | |
Formula: | C18H12 |
Molecular Weight: | 228.293 |
Synonyms: | 1,2,3,4-Dibenznaphthalene;9,10-Benzophenanthrene;9,10-Benzphenanthrene;Benzo[l]phenanthrene;Isochrysene;NSC 57455; |
EINECS: | 205-922-9 |
Density: | 1.19 g/cm3 |
Melting Point: | 195-198 °C(lit.) |
Boiling Point: | 424.998 °C at 760 mmHg |
Flash Point: | 209.141 °C |
Solubility: | 6.6ug/L(25.00 oC) |
Appearance: | white to beige crystalline needles |
Hazard Symbols: | Xi,N |
Risk Codes: | 41 |
Safety: | 22-24/25-61-60-39-26 |
Transport Information: | UN 3077 9/PG 3 |
PSA: | 0.00000 |
LogP: | 5.14620 |
Conditions | Yield |
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With {Co(II)(DBF2)2(H2O)2} In acetonitrile at 20℃; for 18h; Catalytic behavior; Time; Sealed tube; UV-irradiation; Inert atmosphere; | 100% |
With trifluorormethanesulfonic acid; 5% Pd/Al2O3; oxygen In dichloromethane at 20℃; for 1.4h; | 96% |
With iodine In benzene for 168h; UV-irradiation; | 63.9% |
2-(2-bromophenyl)biphenyl
triphenylene
Conditions | Yield |
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With bis(benzonitrile)palladium(II) chloride; caesium carbonate; tris<3,5-bis(trifluoromethyl)phenyl>phosphane In toluene at 110℃; for 24h; | 100% |
Conditions | Yield |
---|---|
With aluminum oxide at 250℃; for 0.166667h; Inert atmosphere; | 99.5% |
With dimethyldimesitylsilane In chlorobenzene at 110℃; for 8h; Friedel Crafts reaction; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon at 300℃; for 10h; Inert atmosphere; | 99% |
palladium on activated charcoal at 310℃; for 25h; | 82% |
5% Pd(II)/C(eggshell) In Exxsol D110 at 225℃; for 40h; Product distribution / selectivity; Industry scale; | 70% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; p-benzoquinone In dimethyl sulfoxide at 140℃; for 4h; Schlenk technique; Inert atmosphere; | 99% |
triphenylene
Conditions | Yield |
---|---|
Stage #1: 1-(biphenyl-2-yl)cyclopent-3-ene-1-carbaldehyde With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 3h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 3h; Reflux; | 97% |
[1,1':2',1"-terphenyl]-2-yl trifluoromethanesulfonate
triphenylene
Conditions | Yield |
---|---|
With potassium carbonate; palladium dichloride; tris[tert-butyl]phosphonium tetrafluoroborate; Trimethylacetic acid at 140℃; for 20h; Schlenk technique; Inert atmosphere; | 96% |
2-chloro-1,1':2',1''-terphenyl
triphenylene
Conditions | Yield |
---|---|
With sodium carbonate In water; acetone for 48h; UV-irradiation; Inert atmosphere; Sealed tube; regioselective reaction; | 95% |
Conditions | Yield |
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With n-butyllithium In hexane at -78 - 25℃; | 93% |
Conditions | Yield |
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With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In 1,2-dimethoxyethane at 135℃; for 24h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere; | A 92% B 10% |
Triphenylene is an organic compound with the formula C18H12, and its systematic name is the same with the product name. With the CAS registry number 217-59-4, it is also named as 9,10-Benzphenanthrene. It belongs to the product categories of Aromatic Hydrocarbons (substituted) & Derivatives; Naphthyridine,Quinoline. Its EINECS number is 205-922-9. In addition, the molecular weight is 228.29. Its classification codes are: (1)Mutation data; (2)Tumor data. It may have uses in optics and electronics. Triphenylene can be isolated from coal tar, but it is also made synthetically using benzyne chemistry, as it is a trimer of benzyne.
Physical properties of Triphenylene are: (1)ACD/LogP: 5.729; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.73; (4)ACD/LogD (pH 7.4): 5.73; (5)ACD/BCF (pH 5.5): 13312.29; (6)ACD/BCF (pH 7.4): 13312.29; (7)ACD/KOC (pH 5.5): 31169.38; (8)ACD/KOC (pH 7.4): 31169.38; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.771; (13)Molar Refractivity: 79.78 cm3; (14)Molar Volume: 191.781 cm3; (15)Polarizability: 31.627×10-24cm3; (16)Surface Tension: 53.54 dyne/cm; (17)Density: 1.19 g/cm3; (18)Flash Point: 209.141 °C; (19)Enthalpy of Vaporization: 65.327 kJ/mol; (20)Boiling Point: 424.998 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25°C.
Preparation: this chemical can be prepared by 1,2,3,4,5,6,7,8,9,10,11,12-dodecahydro-triphenylene at the temperature of 310 °C. This reaction time is 25 hours. This reaction will also need catalyst Pd/C. The yield is about 82%.
Uses of Triphenylene: it can be used to produce triphenylene-2-carbaldehyde at the ambient temperature. It will need reagent TiCl4 and solvent CH2Cl2 with the reaction time of 3 hours. The yield is about 78%.
When you are using this chemical, please be cautious about it as the following:
This chemical has a risk of serious damage to eyes. You should not breathe dust. When using it, you must avoid contact with skin and eyes. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear eye/face protection. This material and its container must be disposed of as hazardous waste. You should avoid releasing it to the environment, and you need to refer to special instructions/safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: c1ccc2c(c1)c3ccccc3c4c2cccc4
(2)Std. InChI: 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
(3)Std. InChIKey: SLGBZMMZGDRARJ-UHFFFAOYSA-N