3,3'-bis{[5-tert-butylsulfanyl-2-(4'-ethynyl-2'-nitrophenyl)ethynylphenyl]ethynyl}tolane

Base Information

Chemical Name:3,3'-bis{[5-tert-butylsulfanyl-2-(4'-ethynyl-2'-nitrophenyl)ethynylphenyl]ethynyl}tolane
CAS No.:914673-97-5
Molecular Formula:C₅₈H₄₀N₂O₄S₂
Molecular Weight:893.099
Hs Code.:

Synonyms:3,3'-bis{[5-tert-butylsulfanyl-2-(4'-ethynyl-2'-nitrophenyl)ethynylphenyl]ethynyl}tolane

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Chemical Property of 3,3'-bis{[5-tert-butylsulfanyl-2-(4'-ethynyl-2'-nitrophenyl)ethynylphenyl]ethynyl}tolane

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Technology Process of 3,3'-bis{[5-tert-butylsulfanyl-2-(4'-ethynyl-2'-nitrophenyl)ethynylphenyl]ethynyl}tolane

There total 14 articles about 3,3'-bis{[5-tert-butylsulfanyl-2-(4'-ethynyl-2'-nitrophenyl)ethynylphenyl]ethynyl}tolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

: 914673-91-9
3,3'-bis{[5-tert-butylsulfanyl-2-(2'-nitro-4'-triisopropylsilylethynylphenyl)ethynyl]phenylethynyl}tolane

: 914673-97-5
3,3'-bis{[5-tert-butylsulfanyl-2-(4'-ethynyl-2'-nitrophenyl)ethynylphenyl]ethynyl}tolane

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃;
DOI:10.1002/ejoc.200600336

Reference yield:

: 350672-95-6
4-fluoro-2-(methoxymethoxy)-1-nitrobenzene

: 914673-97-5
3,3'-bis{[5-tert-butylsulfanyl-2-(4'-ethynyl-2'-nitrophenyl)ethynylphenyl]ethynyl}tolane

Guidance literature:: Multi-step reaction with 8 steps

1.1: 76 percent / dimethylformamide / 1 h / 20 °C

2.1: 95 percent / aq. HCl / methanol / 1 h / 60 °C

3.1: 89 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 88 percent / Pd(PPh₃)4; CuI; triethylamine / tetrahydrofuran / 4 h / 20 °C

5.1: 95 percent / aq. HCl; tin / tetrahydrofuran / 1 h / 20 °C

6.1: BF₃*Et₂O; tert-BuONO / tetrahydrofuran / 0.5 h / -20 - -5 °C

6.2: 38 percent / KI; I₂ / acetonitrile; H₂O; CH₂Cl₂ / 16 h / 20 °C

7.1: 30 percent / Pd(PPh₃)4; CuI; (iPr)2NEt / tetrahydrofuran / 16 h / 20 °C

8.1: 88 percent / glacial acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

With hydrogenchloride; tin; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Sonogashira coupling / 7.1: Sonogashira coupling;
DOI:10.1002/ejoc.200600336

Reference yield:

: 914673-80-6
1,2-bis(3-ethynylphenyl)ethyne

: 914673-97-5
3,3'-bis{[5-tert-butylsulfanyl-2-(4'-ethynyl-2'-nitrophenyl)ethynylphenyl]ethynyl}tolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / Pd(PPh₃)4; CuI; triethylamine / tetrahydrofuran / 4 h / 20 °C

2.1: 95 percent / aq. HCl; tin / tetrahydrofuran / 1 h / 20 °C

3.1: BF₃*Et₂O; tert-BuONO / tetrahydrofuran / 0.5 h / -20 - -5 °C

3.2: 38 percent / KI; I₂ / acetonitrile; H₂O; CH₂Cl₂ / 16 h / 20 °C

4.1: 30 percent / Pd(PPh₃)4; CuI; (iPr)2NEt / tetrahydrofuran / 16 h / 20 °C

5.1: 88 percent / glacial acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

With hydrogenchloride; tin; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1.1: Sonogashira coupling / 4.1: Sonogashira coupling;
DOI:10.1002/ejoc.200600336