288-08-4

Basic information

• Product Name: Telluracyclopentadiene
• Synonyms: Telluracyclopentadiene;Tellurophene
• CAS NO: 288-08-4
• Molecular Formula: C₄H₄Te
• Molecular Weight: 179.67456
• Mol File: 288-08-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 150℃
• Appearance: /
• CAS DataBase Reference: Telluracyclopentadiene(CAS DataBase Reference)
• NIST Chemistry Reference: Telluracyclopentadiene(288-08-4)
• EPA Substance Registry System: Telluracyclopentadiene(288-08-4)

Safety Data

• Hazardous Substances Data: 288-08-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A five-membered monocyclic heteroarene composed of four CH units and one tellurium atom. The parent of the class of tellurophenes.

InChI:InChI=1/C4H4Te/c1-2-4-5-3-1/h1-4H

Synthetic route

acetylene (74-86-2) → Tellurophen (288-08-4) + 2-vinyloxy-1,3-butadiene (57796-76-6) + divinyltellane (63000-06-6)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; tellurium In water at 105 - 115℃; under 15 Torr; for 10h;	A 3% B 4% C 45%
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; tellurium; water at 105 - 115℃; under 11400 Torr; for 10h; Product distribution; Mechanism; various concentration of KOH; various water concentrations; addition of SnCl2;

1,4-Dichloro-2-butyne (821-10-3) → Tellurophen (288-08-4)

Conditions	Yield
With tellurium; sodium tetrahydroborate; potassium hydroxide In 1,4-dioxane; water Inert atmosphere; Cooling with ice;	44%

Butadiyne (460-12-8) → Tellurophen (288-08-4)

Conditions	Yield
With methanol; disodium telluride
With tellurium; sodium tetrahydroborate; water In methanol for 2h;	6.42 g
With tellurium; sodium tetrahydroborate In water Cooling with ice;	5.6 g
With tellurium; sodium tetrahydroborate In ethanol for 2h; Inert atmosphere;
With disodium telluride

acetylene (74-86-2) → Tellurophen (288-08-4)

Conditions	Yield
With aluminum oxide; aluminum telluride

2,3-Dihydro-tellurophen-3-ol → Tellurophen (288-08-4)

Conditions	Yield
In ethanol; acetic acid for 2h; Heating; Yield given;

(1Z,3Z)-1,4-Bis-butyltellanyl-buta-1,3-diene (189068-22-2) → Tellurophen (288-08-4) + dibutyl telluride (38788-38-4)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Title compound not separated from byproducts;

1,1-dibromotellurophene (13129-89-0) → Tellurophen (288-08-4)

Conditions	Yield
With water; potassium carbonate; sodium hydrogensulfite for 0.333333h;	5.0 g

Tellurophen (288-08-4) + phenylmagnesium bromide → (1Z,3Z)-1,4-diphenylbuta-1,3-diene (5807-76-1)

Conditions	Yield
bis(triphenylphosphine)nickel(II) chloride In benzene for 2h; Heating;	88%

Tellurophen (288-08-4) + p-nitrobenzene iodide (636-98-6) → 2-(4-nitrophenyl)tellurophene (1200687-96-2)

Conditions	Yield
Stage #1: Tellurophen With tributyltin chloride In diethyl ether at 20℃; Inert atmosphere; Stage #2: With n-butyllithium In diethyl ether; hexane at 20℃; for 0.75h; Stage #3: p-nitrobenzene iodide With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; Stille coupling; Inert atmosphere;	88%

Tellurophen (288-08-4) + 4-iodobenzonitrile (3058-39-7) → 2,5-bis(4-cyanophenyl)tellurophene (1200687-97-3)

Conditions

Yield

Stage #1: Tellurophen With sec-pentyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; cyclohexane for 0.75h; Inert atmosphere; Reflux; Stage #2: With trimethyltin(IV)chloride In hexane; cyclohexane at 20℃; Stage #3: 4-iodobenzonitrile With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; for 16h; Stille coupling; Inert atmosphere;

88%

Tellurophen (288-08-4) + dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer + silver trifluoromethanesulfonate (2923-28-6) → Rh(C5(CH3)5)(C4H4Te)(2+)*2O3SCF3(1-) = [Rh(C5(CH3)5)(C4H4Te)](O3SCF3)2

Conditions	Yield
In acetone byproducts: AgCl; (argon); addn. of the Ag salt in acetone to a suspn. of the Rh complex and the Te compd. in acetone, stirring (2 h); filtration (Celite), concn. (vac.), pptn. with CHCl3; elem. anal.;	86%

Tellurophen (288-08-4) + trimethyltin(IV)chloride (1066-45-1) → 2,5-bis-(trimethylstannyl)tellurophene (1200687-93-9)

Conditions	Yield
Stage #1: Tellurophen With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In hexane; cyclohexane at 0℃; for 0.75h; Reflux; Stage #2: trimethyltin(IV)chloride In hexane; cyclohexane at 0 - 20℃;	68%

Tellurophen (288-08-4) + p-nitrobenzene iodide (636-98-6) → 2,5-bis(4-nitrophenyl)tellurophene (1200687-99-5)

Conditions

Yield

Stage #1: Tellurophen With sec-pentyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; cyclohexane for 0.75h; Inert atmosphere; Reflux; Stage #2: With trimethyltin(IV)chloride In hexane; cyclohexane at 20℃; Stage #3: p-nitrobenzene iodide With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; for 16h; Stille coupling; Inert atmosphere;

67%

Tellurophen (288-08-4) + n-butyl magnesium bromide (693-03-8) → (5Z,7Z)-5,7-dodecadiene (6108-62-9) + ((1E,3E)-octa-1,3-dien-1-yl)benzene (39491-69-5) + (1Z,3Z)-1-phenyl-1,3-octadiene (39491-67-3)

Conditions	Yield
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In benzene for 6h; Heating;	A 66% B n/a C n/a

Tellurophen (288-08-4) + triiron dodecarbonyl (17685-52-8) → Fe2(CO)6(HCCHCHCH) (129036-04-0, 108034-90-8) + [C4H4Fe2Te(CO)6]

Conditions	Yield
In n-heptane (argon); reflux with stirring (45 min); solvent removal (vac.), chromy. (SiO2; pentane), recrystn. (boiling heptane); elem. anal.;	A n/a B 66%

Tellurophen (288-08-4) + benzophenone (119-61-9) → 2,5-bis[(α-hydroxy-α,α-diphenyl)methyl]tellurophene

Conditions	Yield
Stage #1: Tellurophen With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In hexane; cyclohexane at 0℃; for 0.75h; Inert atmosphere; Reflux; Stage #2: benzophenone In tetrahydrofuran; hexane; cyclohexane at 0 - 20℃; Inert atmosphere;	65%

Tellurophen (288-08-4) → 2-bromotellurophene (59163-67-6)

Conditions	Yield
Stage #1: Tellurophen With n-butyllithium In diethyl ether; hexane at 20℃; for 0.5h; Metallation; Stage #2: With 1,2-dibromo-1,1,2,2-tetrachloroethane at -78 - 20℃; for 3h; Bromination;	64%
With n-butyllithium; 1,2-dibromo-1,1,2,2-tetrachloroethane 1.) ether, -20 deg C; RT, 45 min, 2.) ether, -60 deg C, 3 h; Yield given. Multistep reaction;

Tellurophen (288-08-4) + 4-iodobenzonitrile (3058-39-7) → 2-(4-cyanophenyl)tellurophene (1200687-94-0)

Conditions	Yield
Stage #1: Tellurophen With tributyltin chloride In diethyl ether at 20℃; Inert atmosphere; Stage #2: With n-butyllithium In diethyl ether; hexane at 20℃; for 0.75h; Stage #3: 4-iodobenzonitrile With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; Stille coupling; Inert atmosphere;	64%

Tellurophen (288-08-4) + para-iodoanisole (696-62-8) → 2-(4-methoxyphenyl)tellurophene (75073-61-9)

Conditions	Yield
Stage #1: Tellurophen With tributyltin chloride In diethyl ether at 20℃; Inert atmosphere; Stage #2: With n-butyllithium In diethyl ether; hexane at 20℃; for 0.75h; Stage #3: para-iodoanisole With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; Stille coupling; Inert atmosphere;	63%

Tellurophen (288-08-4) + 4-tolyl iodide (624-31-7) → 2-(4-methylphenyl)tellurophene (1200687-95-1)

Conditions	Yield
Stage #1: Tellurophen With tributyltin chloride In diethyl ether at 20℃; Inert atmosphere; Stage #2: With n-butyllithium In diethyl ether; hexane at 20℃; for 0.75h; Stage #3: 4-tolyl iodide With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; Stille coupling; Inert atmosphere;	62%

Tellurophen (288-08-4) + iodobenzene (591-50-4) → 2-phenyltellurophene

Conditions	Yield
Stage #1: Tellurophen With tributyltin chloride In diethyl ether at 20℃; Inert atmosphere; Stage #2: With n-butyllithium In diethyl ether; hexane at 20℃; for 0.75h; Stage #3: iodobenzene With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; Stille coupling; Inert atmosphere;	61%

Tellurophen (288-08-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → tellurophene-2-carbaldehyde (35273-64-4)

Conditions	Yield
Stage #1: Tellurophen With n-butyllithium In diethyl ether; hexane at 0 - 50℃; for 4.5h; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at -50 - 20℃;	57.7%

Tellurophen (288-08-4) + n-butyl magnesium bromide (693-03-8) + 1,3-bis(di-p-tolylphosphino)propanenickel dichloride → (5Z,7Z)-5,7-dodecadiene (6108-62-9) + 1-Methyl-4-((1Z,3Z)-octa-1,3-dienyl)-benzene

Conditions	Yield
In benzene Heating;	A 56% B 6%

Tellurophen (288-08-4) + 4-tolyl iodide (624-31-7) → 2,5-bis(4-methylphenyl)tellurophene (1200687-98-4)

Conditions

Yield

Stage #1: Tellurophen With sec-pentyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; cyclohexane for 0.75h; Inert atmosphere; Reflux; Stage #2: With trimethyltin(IV)chloride In hexane; cyclohexane at 20℃; Stage #3: 4-tolyl iodide With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; for 16h; Stille coupling; Inert atmosphere;

47%

Tellurophen (288-08-4) → 1,1-dibromotellurophene (13129-89-0)

Conditions	Yield
With bromine In methanol	45%

Tellurophen (288-08-4) + triiron dodecarbonyl (17685-52-8) → Iron-Tellurium + Fe2(CO)6(HCCHCHCH) (129036-04-0, 108034-90-8)

Conditions	Yield
In n-heptane (argon); reflux with stirring (2.5 h); filtration, solvent removal (vac.); elem. anal.;	A n/a B 45%

Tellurophen (288-08-4) + iodobenzene (591-50-4) → 2,5-bis-(phenyl)tellurophene (19477-77-1)

Conditions	Yield
Stage #1: Tellurophen With sec-pentyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; cyclohexane for 0.75h; Inert atmosphere; Reflux; Stage #2: With trimethyltin(IV)chloride In hexane; cyclohexane at 20℃; Stage #3: iodobenzene With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; for 16h; Stille coupling; Inert atmosphere;	42%

Tellurophen (288-08-4) + para-iodoanisole (696-62-8) → 2,5-bis(4-methoxyphenyl)tellurophene (219540-20-2)

Conditions

Yield

Stage #1: Tellurophen With sec-pentyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; cyclohexane for 0.75h; Inert atmosphere; Reflux; Stage #2: With trimethyltin(IV)chloride In hexane; cyclohexane at 20℃; Stage #3: para-iodoanisole With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 50 - 60℃; for 16h; Stille coupling; Inert atmosphere;

42%

Tellurophen (288-08-4) + Ru3(CO)10(acetonitrile)2 (103257-53-0) → Ru2(CO)6(C4H4)

Conditions	Yield
In dichloromethane stirred at room temp. for 10 min.;; removal of the solvent and TCL of the residue (SiO2; eluant: pentane);;	40%

Tellurophen (288-08-4) → 2,2'-bitellurophene

Conditions	Yield
Stage #1: With n-butyllithium In diethyl ether; hexane at 20℃; for 0.5h; Metallation; Stage #2: Tellurophen With copper dichloride In diethyl ether; hexane at -78℃; for 3h; Dimerization;	39%
Stage #1: Tellurophen With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - 20℃; Inert atmosphere; Stage #2: With copper dichloride In tetrahydrofuran; pentane at 20℃; Inert atmosphere;	30%
With n-butyllithium; copper dichloride 1.) ether, -20 deg C; RT, 45 min, 2.) ether, -70 deg C; RT, 1 d; Yield given. Multistep reaction;
With n-butyllithium; copper(l) chloride 1.) Et2O, hexane, RT, 45 min, 2.) Et2O, hexane, RT, overnight; Yield given; Multistep reaction;

Tellurophen (288-08-4) + bis(acetonitrile)decacarbonyltriosmium (61817-93-4, 146143-79-5, 871132-66-0) → Os3(CO)10(C4H4Te)

Conditions	Yield
In dichloromethane at room temp. the reaction mixt. was stirred for 30 min; sepd. by TLC;	38%

Tellurophen (288-08-4) + bis(acetonitrile)decacarbonyltriosmium (61817-93-4, 146143-79-5, 871132-66-0) → {Os3(μ-C4H4Te)(CO)10}

Conditions	Yield
In cyclohexane The bis-acetonitrile-complex reacts with tellurophene in refluxing cyclohexane for 20 min.;	35%

Tellurophen (288-08-4) + triiron dodecarbonyl (17685-52-8) → Fe2(CO)6(C4H4)

Conditions	Yield
In cyclohexane refluxed;; removal of the solvent under reduced pressure sepd. by TLC (SiO2; eluant petroleum ether);;	25%

Tellurophen (288-08-4) → 2,5-dibromotellurophene

Conditions	Yield
Stage #1: Tellurophen With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In hexane; cyclohexane at 0 - 65℃; for 0.75h; Inert atmosphere; Stage #2: With 1,2-dibromo-1,1,2,2-tetrachloroethane In diethyl ether; hexane; cyclohexane at -78 - 20℃; Inert atmosphere;	25%

Tellurophen (288-08-4) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)tellurophene

Conditions	Yield
Stage #1: Tellurophen With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In hexane; cyclohexane at 0℃; for 0.75h; Inert atmosphere; Reflux; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexane; cyclohexane at 0 - 20℃; Inert atmosphere;	20%

Upstream product

• 460-12-8 Butadiyne 
• 74-86-2 acetylene 
• 13129-89-0 1,1-dibromotellurophene 
• 821-10-3 1,4-Dichloro-2-butyne 
• 189068-22-2 (1Z,3Z)-1,4-Bis-butyltellanyl-buta-1,3-diene 

Downstream Products

• 6108-62-9 (5Z,7Z)-5,7-dodecadiene 
• 39491-69-5 ((1E,3E)-octa-1,3-dien-1-yl)benzene 
• 39491-67-3 (1Z,3Z)-1-phenyl-1,3-octadiene 
• 39491-56-0 (Z)-penta-1,3-dienylbenzene 
• 6108-61-8 cis,cis-2,4-Hexadien 
• 5807-76-1 (1Z,3Z)-1,4-diphenylbuta-1,3-diene 
• 35273-64-4 2-formyl-tellurophen 
• 35246-22-1 Tellurophen-2-carbonsaeure 
• 1200687-99-5 2,5-bis(4-nitrophenyl)tellurophene 
• 1200687-96-2 2-(4-nitrophenyl)tellurophene 
• 19477-77-1 2,5-bis-(phenyl)tellurophene 
• 1200687-98-4 2,5-bis(4-methylphenyl)tellurophene 
• 1200687-95-1 2-(4-methylphenyl)tellurophene 
• 219540-20-2 2,5-bis(4-methoxyphenyl)tellurophene 

Relevant articles and documents

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Synthesis of Diphenylchalcogenophene Diboronic Acid Bis(pinacol) Esters and Halogen Photoelimination from Tellurium by Triplet–Triplet Annihilation

The synthesis of diphenylthiophene-, diphenylselenophene-, and diphenyltellurophene-based diboronic bis(pinacol) esters and their optoelectronic properties is reported. The addition of bromine to the borylated diaryltellurophene and subsequent photoelimination are investigated. The photochemical quantum yield of bromine photoelimination is (9.7±0.2) % at a 4.4 m trap (2,3-dimethyl-1,3-butadiene) concentration. It is found that the bromine photoelimination reaction can also be driven by the incorporation of a triplet sensitizer through a triplet–triplet annihilation process.

A novel tellurophene-containing conjugated polymer with a dithiophenyl diketopyrrolopyrrole unit for use in organic thin film transistors

A new tellurophene-based π-conjugated polymer, PDTDPPTe, was synthesized. PDTDPPTe exhibits a smaller optical band gap (Eg opt = 1.25 eV) than thiophene-based PDTDPPT (Eg opt = 1.30 eV). Thin-film transistors comprising PDTDPPTe displayed outstanding performance (μmax = 1.78 cm2 V-1 s-1, Ion/Ioff = 105-6).