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Cas Database |
| Name |
Triphenylethylene |
EINECS | 200-395-1 |
| CAS No. | 58-72-0 | Density | 1.072 g/cm3 |
| PSA | 0.00000 | LogP | 5.27550 |
| Solubility | N/A | Melting Point |
68-71 °C |
| Formula | C20H16 | Boiling Point | 358.2 °C at 760 mmHg |
| Molecular Weight | 256.347 | Flash Point | 165 °C |
| Transport Information | N/A | Appearance | White to slightly beige powder |
| Safety | 26-36/37-60-61 | Risk Codes | 22-36-50/53 |
| Molecular Structure |
|
Hazard Symbols |
 Xn, N
|
| Synonyms |
Ethylene,triphenyl- (6CI,8CI);1,1,2-Triphenylethene;1,1,2-Triphenylethylene;Benzilidenediphenylmethane;NSC 17535;Triphenylethene;Triphenylethylene; |
Article Data | 274 |
Triphenylethylene Synthetic route
| Conditions | Yield |
|---|---|
| With water; acetic acid; bis-triphenylphosphine-palladium(II) chloride at 20℃; for 6h; | 100% |
| With bis-triphenylphosphine-palladium(II) chloride; water; acetic acid at 20℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube; | 94% |
- 591-50-4
iodobenzene
- 173603-23-1
(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
- 58-72-0
Triphenylethylene
| Conditions | Yield |
|---|---|
| With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 70℃; for 4h; Suzuki-Miyaura Coupling; | 100% |
- 384360-11-6
1-dimethyl(2-pyridyl)silyl-1,2,3-triphenylethene
- 58-72-0
Triphenylethylene
| Conditions | Yield |
|---|---|
| With tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 1h; | 99% |
| Conditions | Yield |
|---|---|
| With tetraethylammonium perchlorate; triethylamine In ethanol; dimethyl sulfoxide at 20℃; for 18h; Electrolysis; Green chemistry; | 98% |
| With lithium aluminium tetrahydride; nickel dichloride In tetrahydrofuran < 0 deg C; | 95% |
| With lithium aluminium tetrahydride; nickel dichloride In tetrahydrofuran Product distribution; < 0 deg C; other triarylvinyl halogenides, other transition metal halides; | 95% |
| With 2,3-diethynylquinoxaline; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 25℃; Product distribution; Rate constant; Thermodynamic data; -1.2 V vs. Ag/AgI; various mediators; indirect electrochemical reduction of vinyl halides and related compounds; rate constants and free energies of activation for electron transfer from electrochemically generated anion radicals to vinyl halides; | |
| With Diethyl phosphonate; tert-butyl alcohol In acetonitrile at 25℃; Product distribution; Kinetics; Further Variations:; Solvents; |
| Conditions | Yield |
|---|---|
| Stage #1: phenylmagnesium bromide; diphenyl acetylene With nickel(II) chloride hexahydrate In tetrahydrofuran; toluene at 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: With water In tetrahydrofuran; toluene Catalytic behavior; Reagent/catalyst; Solvent; Concentration; Inert atmosphere; Schlenk technique; | 98% |
| With manganese(ll) chloride In tetrahydrofuran; toluene at 100℃; for 4h; | 60% |
| Stage #1: phenylmagnesium bromide; diphenyl acetylene With 1,1'-bis-(diphenylphosphino)ferrocene; iron(III)-acetylacetonate; 1,2-dichloro-2-methylpropane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride In tetrahydrofuran; water Catalytic behavior; Reagent/catalyst; | 24 %Chromat. |
| Conditions | Yield |
|---|---|
| With silver(I) acetate; palladium diacetate; acetic acid at 110℃; for 6h; Heck reaction; | 97% |
| With dipalladium(II)(1,1'-di-t-butyl-3,3'-(1,2-ethanediyl)bisimidazolium)dipyridinetetradichloride; tetrabutylammomium bromide; sodium acetate In N,N-dimethyl acetamide at 120℃; for 18h; Heck Reaction; Inert atmosphere; | 71% |
| Conditions | Yield |
|---|---|
| With 15-crown-5; sodium hydride In tetrahydrofuran at 0 - 25℃; for 3h; | 96% |
| With potassium tert-butylate; toluene |
| Conditions | Yield |
|---|---|
| With triethylamine; bis(acetato)bis(triphenylphosphine)palladium(0) In acetonitrile at 80℃; for 3.5h; | 96% |
| With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; chlorobenzene In ethanol at 70℃; for 2h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 80% |
- 22021-09-6
1,2,2-triphenyl-1-iodoethylene
A
- 58-72-0
Triphenylethylene
B
- 1836-87-9
9-Benzylidene-9H-fluorene
| Conditions | Yield |
|---|---|
| With palladium diacetate; cesium pivalate; bis-diphenylphosphinomethane In N,N-dimethyl-formamide at 100℃; for 24h; | A 4% B 96% |
| With sodium acetate; dimethyl amine; bis-diphenylphosphinomethane; palladium diacetate at 100℃; for 36h; | A 48% B 52% |
| Conditions | Yield |
|---|---|
| With (N,N-diisopropylamino)diphenylphosphine; potassium carbonate; palladium dichloride In tetrahydrofuran at 20 - 65℃; Inert atmosphere; | 96% |
| With acetic acid; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 12h; | 91% |
| With water; palladium diacetate; bis(pinacol)diborane; tricyclohexylphosphine In tetrahydrofuran at 80℃; for 4h; | 90% |
Triphenylethylene Consensus Reports
Reported in EPA TSCA Inventory.
Triphenylethylene Specification
The Triphenylethylene with CAS registry number of 58-72-0 is also known as Benzilidenediphenylmethane. The IUPAC name is 1,2-Diphenylethenylbenzene. It belongs to product categories of Miscellaneous; Acyclic; Alkenes; Organic Building Blocks. Its EINECS registry number is 200-395-1. In addition, the formula is C20H16 and the molecular weight is 256.34. This chemical is a white to slightly beige powder and should be sealed in cool place.
Physical properties about Triphenylethylene are: (1)ACD/LogP: 7.00; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7; (4)ACD/LogD (pH 7.4): 7; (5)ACD/BCF (pH 5.5): 122037.29; (6)ACD/BCF (pH 7.4): 122037.29; (7)ACD/KOC (pH 5.5): 152226.2; (8)ACD/KOC (pH 7.4): 152226.2; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.645; (11)Molar Refractivity: 86.68 cm3; (12)Molar Volume: 239 cm3; (13)Surface Tension: 44.2 dyne/cm; (14)Density: 1.072 g/cm3; (15)Flash Point: 165 °C; (16)Enthalpy of Vaporization: 57.99 kJ/mol; (17)Boiling Point: 358.2 °C at 760 mmHg; (18)Vapour Pressure: 5.34E-05 mmHg at 25 °C.
Preparation of Triphenylethylene: it is prepared by reaction of benzophenone with benzylphosphonic acid diethyl ester. The reaction needs reagents NaH, 15-crown-5 and solvent tetrahydrofuran at the temperature of 0-25 °C for 3 hours. The yield is about 96%.
Uses of Triphenylethylene: it is used to produce triphenyl-oxirane. The reaction occurs with reagents oxone, tetrahydrothiopyran-1,1,4-trione, sodium bicarbonate, aq. Na2*EDTA and solvent acetonitrile at ambient temperature for 6 hours. The yield is about 97%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes and harmful if swallowed. What's more, it is very toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing and gloves. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. Besides, this material and its container must be disposed of as hazardous waste. Avoid release to the environment.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C3=CC=CC=C3
2. InChI: InChI=1S/C20H16/c1-4-10-17(11-5-1)16-20(18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-16H
3. InChIKey: MKYQPGPNVYRMHI-UHFFFAOYSA-N
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