TPP CAS#: 917-23-7 (20998-75-8); ChemWhat Code: 71635

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameTPP
IUPAC Name5,10,15,20-tetraphenyl-21,23-dihydroporphyrin
Molecular StructureTPP
CAS Registry Number 917-23-7
20998-75-8
EINECS Number213-025-9
MDL NumberMFCD00011680
Beilstein Registry Number379542
Synonymsmeso-Tetraphenylporphyrin; 5,15,10,20-tetraphenylporphyrin, 5,10,15,20-tetraphenyl-21H,23H-porphine, 5,10,15,20-tetrakis-(phenyl)-21,23H-porphyrin, 5,10,15,20-meso-tetrakis(4-phenyl)porphyrin, 5,10,15,20-tetraphenyl-21H,23H-porphyrin, 5,10,15,20-Tetraphenyl-21H,23H-porphine, 5,10,15,20-tetrakis(phenyl)porphyrinate; 20998-75-8; 917-23-7
Molecular FormulaC44H30N4
Molecular Weight614.749
InChIInChI=1S/C44H30N4/c1-5-13-29(14-6-1)41-33-21-23-35(45-33)42(30-15-7-2-8-16-30)37-25-27-39(47-37)44(32-19-11-4-12-20-32)40-28-26-38(48-40)43(31-17-9-3-10-18-31)36-24-22-34(41)46-36/h1-28,45,48H
InChI KeyYNHJECZULSZAQK-UHFFFAOYSA-N
Canonical SMILESC1=CC=C(C=C1)C2=C3C=CC(=C(C4=NC(=C(C5=CC=C(N5)C(=C6C=CC2=N6)C7=CC=CC=C7)C8=CC=CC=C8)C=C4)C9=CC=CC=C9)N3
Patent Information
Patent IDTitlePublication Date
EP1672961COMPOUND, CHARGE TRANSPORT MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE2006
EP1829871ORGANIC COMPOUND, CHARGE-TRANSPORTING MATERIAL, AND ORGANIC ELECTROLUMINESCENT ELEMENT2015
US6316493Substituted 1,2,4-trioxanes as antimalarial agents and a process of producing the substituted 1,2,4-trioxanes2001
US2002/155099TRANSFER OF MOLECULES INTO THE CYTOSOL OF CELLS2002

Physical Data

AppearanceBlue to purple crystalline powder
SolubilityInsoluble in water
Melting Point, °C Solvent (Melting Point) Comment (Melting Point)
250ethanol
300
450benzeneSublimation.at:>400 degreeC.Zers..
Density, g·cm-3Measurement Temperature, °CType (Density)
1.27620crystallographic
Description (Adsorption (MCS))Temperature (Adsorption (MCS)), °CComment (Adsorption (MCS)) Partner (Adsorption (MCS))
Further physical properties of the adsorbed moleculeX-ray diffractionAg(111)
Further physical properties of the adsorbed molecule26.84Cu
Further physical properties of the adsorbed molecule24.85polarizedtoluene
Description (Association (MCS))Solvent (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))
Association with compoundaq. buffer, N,N-dimethyl-formamide19.99bovine serum albumin
Association with compoundchloroform-d1-322-phenoxypropionic acid
Association with compounddichloromethane9,10-phenanthrenequinone
Association with compoundcyclohexane20fullerene-C60

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts, Spectrum1Hchloroform-d1500
Chemical shifts, Spectrum13Cchloroform-d1100
TPP CAS 917-23-7 HNMRTPP CAS 917-23-7 HNMR
TPP CAS 917-23-7 HNMR PartTPP CAS 917-23-7 HNMR part
Description (IR Spectroscopy)Solvent (IR Spectroscopy)
Bandspotassium bromide
Description (ESR Spectroscopy) Solvents (ESR Spectroscopy)Temperature (ESR Spectroscopy), °C
Spectrumsolid matrix-269.16
Spectrumnematic phase-133.2

Route of Synthesis (ROS)

Route of Synthesis (ROS) of TPP CAS 917-23-7
Route of Synthesis (ROS) of TPP CAS 917-23-7
ConditionsYield
Stage #1: benzaldehyde; 5-phenyldipyrromethane With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.5h;
Stage #2: With selenium(IV) oxide In dichloromethane at 20℃; for 1h;

Experimental Procedure
Under room temperature, aryl aldehyde (1 mmol), BF3O(Et)2 (70 μL from a freshly prepared 1 M solution in CH2Cl2) and then pyrrole (70 μL, 1 mmol) were added successively to 10 mL CH2Cl2; reaction was then stirred for 30 min. Finely powdered SeO2 (1670 g, 15 mmol) was sequentially added under vigorous stirring and reaction was then kept for additional 60 min. The resulting mixture was directly filtered through a Celite pad, evaporated on Silica 60 and purified by flash chromatography (Silica 60, 20 .x. 150 mm) with hexanes/CH2Cl2 (2:1) for 1, CHCl3/hexanes (3:2) for 2, CHCl3/hexanes (1:2) for 5, CHCl3/(Et)2O/hexanes (5:2:4) for 3 and CHCl3/hexanes (1:1) for 4 with yields shown in Table 2. Compounds spectrometric properties coincided with literature data (for details, see Supplementary data). 		65%
Stage #1: benzaldehyde; 5-phenyldipyrromethane With Indion-130 resin In dichloromethane at 25℃; for 16h;
Stage #2: With chloranil In dichloromethane for 3h; Heating;		24%

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH302: Harmful if swallowed [Warning Acute toxicity, oral]
H312: Harmful in contact with skin [Warning Acute toxicity, dermal]
H332: Harmful if inhaled [Warning Acute toxicity, inhalation]
Information may vary between notifications depending on impurities, additives, and other factors. 
Precautionary Statement CodesP261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501
(The corresponding statement to each P-code can be found at the?GHS Classification?page.)

Other Data

TransportationNot dangerous goods
Under the room temperature and away from light
HS Code290621
StorageUnder the room temperature and away from light
Shelf Life1 year
Market PriceUSD 2600/kg
Use Pattern
Nano-technology
in combination with fullerene (C60)
organic Field-Effect Transistor (OFET)
filter that inhibits transmission of light having a wavelength in the 450+/−50 nm range
detecting a cathepsin E expressing cell in vitro or in vivo

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