9,10-Diphenylanthracene

Iupac Name：9,10-diphenylanthracene

Molecular Weight：330.43

Modify Date.: 2022-11-29 08:31

Introduction:

slightly yellow powderChEBI: A member of the class of anthracenes that is anthracene in which both of the hydrogens on the central ring are substituted by phenyl groups.

9,10-diphenylanthracene is a member of the class of anthracenes that is anthracene in which both of the hydrogens on the central ring are substituted by phenyl groups. It has a role as a fluorochrome and a photosensitizing agent.

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1. Names and Identifiers

: 1.1 Name; 9,10-Diphenylanthracene; 1.2 Synonyms; 9, 9-diphenylanthracene 9,10-biphenylanthracene 9,10-Dipehnylphenanthrene 9,10-Diphenyla 9,10-Diphenylanthrac 9,10-DIPHENYLANTHRACEN 9,10-diphenyl-anthracen 9,10-diphenyl-anthracene 9,10-Diphenylanthracene (purified by subliMation) 9,10-diphenylanthrance 9,9-diphenylanthracene Anthracene, 9,10-diphenyl- anthracene,9,10-diphenyl DPHA、DPA EINECS 216-105-1 MFCD00001253 Purple fluorescence dye DPHA; View all

1.3 CAS No.: 1499-10-1

1.4 CID: 15159

1.5 EINECS(EC#): 216-105-1

1.6 Molecular Formula: C26H18 (isomer)

1.7 Inchi: InChI=1S/C26H18/c1-3-11-19(12-4-1)25-21-15-7-9-17-23(21)26(20-13-5-2-6-14-20)24-18-10-8-16-22(24)25/h1-18H

1.8 InChIkey: FCNCGHJSNVOIKE-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C(C=C1)C2=C3C=CC=CC3=C(C4=CC=CC=C42)C5=CC=CC=C5

1.10 Isomers Smiles: C1=CC=C(C=C1)C2=C3C=CC=CC3=C(C4=CC=CC=C42)C5=CC=CC=C5

2. Properties

2.1 Density: 1.146

2.1 Melting point: 245-248℃

2.1 Boiling point: 469.1 °C at 760 mmHg

2.1 Refractive index: 1.697

2.1 Flash Point: 234.7 °C

2.1 Precise Quality: 330.14100

2.1 PSA: 0.00000

2.1 logP: 7.32700

2.1 Λmax: 393nm(Cyclohexane)(lit.)

2.2 Appearance: Light yellow to beige Fine Crystalline Powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: slightly yellow powder

2.5 Color/Form: Light yellow to beige

2.6 Water Solubility: INSOLUBLE

2.7 Stability: Stable. Combustible. Incompatible with strong oxidizing agents.

2.8 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Definition: ChEBI: A member of the class of anthracenes that is anthracene in which both of the hydrogens on the central ring are substituted by phenyl groups.

3.2 Methods of Manufacturing: General procedure: An oven-dried Schlenk flask, equipped with a magnetic stir bar, septum, and a condenser was charged with aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), K2CO3 (2 mmol), 4 (0.143 g, 1 mol %), and 5 mL of solvent. The flask was immersed in an oil bath and stirred at 80 C. Upon complete consumption of starting materials as determined by TLC analysis, the reaction mass was filtered and the solid washed with water (2Chi5 mL), and extracted with diethyl ether (3Chi5 mL). The combined organic layers were collected, dried over anhydrous Na2SO4, and concentrated in vacuum to afford product which was purified by silica gel column chromatography (n-hexane/EtOAc = 9:1)General procedure: An oven-dried Schlenk flask, equipped with a magneticstir bar, a septum and a condenser was charged with arylhalide (1.0 mmol), arylboronic acid (1.2 mmol), the gelentrappedbase (1 g, 2 mmol), Pd(dppf)Cl2 (0.0085 g, 1 mol%) and 5 mL of 95% ethanol. The flask was immersedand stirred in an oil bath at 80 8C. Upon completeconsumption of starting materials as determined by TLCanalysis, the gel was separated by filtration and water(10 mL) was added. The filtrate was extracted with diethylether (3 5 mL). The combined organic layer was collected, dried over anhydrous Na2SO4 and concentratedunder vacuum to afford the product, which was purified bysilica gel column chromatography (n-hexane:ethyl acetate9:1)General procedure: A general Pd-catalyzed coupling reaction procedure is explained with the case of 1, 4-diphenylnaphthalene 14DPN: A mixture of 1, 4-dibromonaphthalene (0.57 g, 2.0 mmol), phenylboronic acid (0.55 g, 4.5 mmol), sodium carbonate (0.54 g, 5.0 mmol), water (5 mL) and toluene (32 mL) in a 100 mL two-necked round bottom flask was sealed with septa and deoxygen by bubbling with nitrogen gas for 40 minitues. Afterwards tetrakis(triphenylphosphine)palladium (47 mg, 0.045 mmol) was quickly added into the mixture by opening the septum, and the mixture was deoxygen for additional 10 minitues. The reaction was kept at 80 C uner a nitrogen atmosphere for 24 hours. After cooled down to room temperature, the reaction was extracted with ethylacetate and water for three times. The oragnic layer was collected, and the solvent was removed by a rotary evaporator. The residue was purified by silica gel chromatagraphy with hexane and dichloromethane (15:1) as the elute to afford a white solid, 1, 4-diphenylnaphthalene 14DPN (0.47 g, 1.68 mmol), in a 84 % yield.; View all

3.3 Purification Methods: Crystallise the anthracene from acetic acid or xylene [Baumstark et al. J Org Chem 52 3308 1987]. [Beilstein 5 IV 2807.] 9,10-DiphenylanthraceneSupplier

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S24/25

4.1 Hazard Declaration: H315

4.1 RIDADR: 2811

4.1 Caution Statement: P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 3

4.1 RTECS: SS6825000

4.1 Safety: Hazard Codes: Xi
Risk Statements:
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements:
22: Do not breathe dust
24: Avoid contact with skin
25: Avoid contact with eyes
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves

4.2 Specification: 9,10-Diphenylanthracene (1499-10-1),a polycyclic aromatic hydrocarbon, which also can be called for Diphenylanthracene ; anthracene, 9,10-diphenyl- .It is used as a sensitiser in chemoluminescence. In lightsticks it is used to produce blue light.And it is a molecular organic semiconductor used in OLED-based displays and blue OLEDs.
9,10-Diphenylanthracene (1499-10-1) is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration While not breathing. When breathing is difficult, give oxygen.And as soon as to get medical aid.Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.In addition, 9,10-Diphenylanthracene (1499-10-1) can be stable under normal temperature and pressure conditions.It is not compatible with strong oxidizing agents and you must not take it with incompatible materials.And also prevent it to broken down into hazardous decomposition products: carbon dioxide,carbon monoxide.; View all

4.3 Toxicity: Carcinogenicity of 9,10-Diphenylanthracene (1499-10-1) hasn't been listed as a carcinogen by NTP, IARC,ACGIH, or CA Prop 65. And its toxicological properties have not been fully investigated.You can see actual entry in RTECS for complete information.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : KBr disc

Mass

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

1499-10-1Total: 95 Synthesis Route

71-43-2 202 Suppliers

1499-10-1 129 Suppliers

Literatures:
Chemische Berichte, , vol. 64, p. 2194,2199
Yield: null

91-01-0 288 Suppliers

1499-10-1 129 Suppliers

Literatures:
Chemische Berichte, , vol. 61, p. 1677
Yield: null

605-48-1 16 Suppliers

1499-10-1 129 Suppliers

Literatures:
Wako Pure Chemical Industries, Ltd. Patent: US6566572 B2, 2003 ;
Yield: ~86%

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8. Precursor and Product

precursor:

4122-56-9

470-35-9

6486-01-7

1499-10-1

120-12-7

15257-17-7

6318-17-8

91-01-0

523-27-3

781-43-1

40112-58-1

3129-17-7

71-43-2

66774-02-5

605-48-1

1560-32-3

19061-38-2

803-58-7

119-61-9

119-67-5

View all

product :

6486-01-7

1499-10-1

3744-21-6

70942-81-3

15257-17-7

6318-17-8

2154-56-5

16331-65-0

781-43-1

2348-55-2

2819-03-6

38399-73-4

2026-21-3

90624-31-0

2492-36-6

1159-86-0

View all

9. Other Information

9.0 BRN: 1914010

9.1 Chemical Properties: slightly yellow powder

9.2 Definition: ChEBI: A member of the class of anthracenes that is anthracene in which both of the hydrogens on the central ring are substituted by phenyl groups.

9.3 Purification Methods: Crystallise the anthracene from acetic acid or xylene [Baumstark et al. J Org Chem 52 3308 1987]. [Beilstein 5 IV 2807.]

9.4 Storage Conditions: General procedure: An oven-dried Schlenk flask, equipped with a magnetic stir bar, septum, and a condenser was charged with aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), K2CO3 (2 mmol), 4 (0.143 g, 1 mol %), and 5 mL of solvent. The flask was immersed in an oil bath and stirred at 80 C. Upon complete consumption of starting materials as determined by TLC analysis, the reaction mass was filtered and the solid washed with water (2Chi5 mL), and extracted with diethyl ether (3Chi5 mL). The combined organic layers were collected, dried over anhydrous Na2SO4, and concentrated in vacuum to afford product which was purified by silica gel column chromatography (n-hexane/EtOAc = 9:1)General procedure: An oven-dried Schlenk flask, equipped with a magneticstir bar, a septum and a condenser was charged with arylhalide (1.0 mmol), arylboronic acid (1.2 mmol), the gelentrappedbase (1 g, 2 mmol), Pd(dppf)Cl2 (0.0085 g, 1 mol%) and 5 mL of 95% ethanol. The flask was immersedand stirred in an oil bath at 80 8C. Upon completeconsumption of starting materials as determined by TLCanalysis, the gel was separated by filtration and water(10 mL) was added. The filtrate was extracted with diethylether (3 5 mL). The combined organic layer was collected, dried over anhydrous Na2SO4 and concentratedunder vacuum to afford the product, which was purified bysilica gel column chromatography (n-hexane:ethyl acetate9:1)General procedure: A general Pd-catalyzed coupling reaction procedure is explained with the case of 1, 4-diphenylnaphthalene 14DPN: A mixture of 1, 4-dibromonaphthalene (0.57 g, 2.0 mmol), phenylboronic acid (0.55 g, 4.5 mmol), sodium carbonate (0.54 g, 5.0 mmol), water (5 mL) and toluene (32 mL) in a 100 mL two-necked round bottom flask was sealed with septa and deoxygen by bubbling with nitrogen gas for 40 minitues. Afterwards tetrakis(triphenylphosphine)palladium (47 mg, 0.045 mmol) was quickly added into the mixture by opening the septum, and the mixture was deoxygen for additional 10 minitues. The reaction was kept at 80 C uner a nitrogen atmosphere for 24 hours. After cooled down to room temperature, the reaction was extracted with ethylacetate and water for three times. The oragnic layer was collected, and the solvent was removed by a rotary evaporator. The residue was purified by silica gel chromatagraphy with hexane and dichloromethane (15:1) as the elute to afford a white solid, 1, 4-diphenylnaphthalene 14DPN (0.47 g, 1.68 mmol), in a 84 % yield.; View all

9.5 Mesh Entry Terms: 9,10-diphenylanthracene

9.6 Manufacturing Info: Anthracene, 9,10-diphenyl-: ACTIVE

9.7 Uses: 9,10-Diphenylanthracene is a polycyclic aromatic hydrocarbon and a useful organic semiconductor. 9,10-Diphenylanthracene is also a sensitiser in chemiluminescence. It has applications related to OLEDs and OLED-based displays.

9.8 General Description: 9,10-Diphenylanthracene, an aromatic hydrocarbon, is a blue light emitting material that is used for the measurement of fluorescence quantum yields in dilute solutions. Its derivatives show potential candidature in organic light emitting diode (OLED) devices. It is also used as a fluorophore for the study of peroxyoxalate chemiluminescence (POCL).

9.9 Usage: 9,10-Diphenylanthracene acts as a sensitizer in chemiluminescence. It is used in light sticks in order to produce blue light. It is also useful in blue organic light-emitting diodes (OLEDs) and OLED-based displays. Further, it plays an important role in the preparation of 9,10-difluoro-9,10-diphenyl-9,10-dihydro-anthracene. In addition to this, it is used as an organic semiconductor.

10. Computational chemical data

Molecular Weight: 330.43g/mol
Molecular Formula: C₂₆H₁₈
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 330.140850574
Monoisotopic Mass: 330.140850574
Complexity: 375
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Topological Polar Surface Area: 0
Heavy Atom Count: 26
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4AAAAAAAAAAAAAAAAAAAAAAAAAAAwYMGDAAAAAADBVAAAGAAAAAAADACAGAAwAMAAAACAAiBCAAACAAAgAAAIiAAAAIgIICKAERCAIAAggAAIiAcAgMAOwAACAAAQAACAAAQAACAAAAAAAAAAAA==

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