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inquiryProduct Name: 1,4-Diethynyjbenzene CAS No.: 935-14-8 Molecular Formula: C10H6 Molecular Weight: 126.15 Grade Standard: Reagent grade Appearance: Crystalline Powder Appearance:White powder Storage: Room Temperature Package: 25kg/drum or 20
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1,4-Bis(trimethylsilylethynyl)benzene
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With potassium carbonate In methanol; dichloromethane at 20℃; for 1h; | 100% |
With water; potassium hydroxide In methanol for 1h; | 100% |
With potassium carbonate In methanol at 20℃; | 97% |
Conditions | Yield |
---|---|
Stage #1: para-diiodobenzene; trimethylsilylacetylene With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Sonogahira-Hagihara coupling reaction; Stage #2: With potassium carbonate In methanol | 100% |
1,4-bis(2,2-dibromoethenyl)benzene
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; | 99% |
With caesium carbonate; dimethyl sulfoxide at 115℃; for 12h; | 95% |
With Succinimide; potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Schlenk technique; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
With potassium hydroxide In toluene for 3h; Reflux; Inert atmosphere; Darkness; | 98% |
With sodium isopropylate In isopropyl alcohol for 4.5h; Heating; | 85% |
With aluminum oxide; potassium hydroxide for 0.0166667h; microwave irradiation; | 84% |
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 115℃; for 12h; | 98% |
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; methanol at 0℃; Inert atmosphere; | 97% |
terephthalaldehyde,
(dibromomethyl)(triphenyl)phosphonium bromide
1,4-diethynylbenzene
Conditions | Yield |
---|---|
Stage #1: terephthalaldehyde,; (dibromomethyl)(triphenyl)phosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.0833333h; Wittig-type condensation; Stage #2: With potassium tert-butylate In tetrahydrofuran at -78℃; Elimination; | 85% |
1,1'-(1,4-phenylene)bis(3-phenylprop-2-yn-1-one)
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With potassium hydroxide; water In benzene at 80℃; | 83% |
1,4-Bis(trimethylsilylethynyl)benzene
1,4-diethynylbenzene
Conditions | Yield |
---|---|
In methanol; dichloromethane; water | 78% |
Conditions | Yield |
---|---|
Stage #1: 1,4-Diacetylbenzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Enolization; Stage #2: With diethyl chlorophosphate In tetrahydrofuran at -78℃; for 0.25h; Phosphorylation; Stage #3: With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 4h; Dehydration; | 77% |
(i) PCl5, (ii) NaNH2, liq. NH3; Multistep reaction; |
(Z,Z)-1,4-bis(2-bromoethenyl)benzene
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 25℃; for 3h; | 73% |
Conditions | Yield |
---|---|
Stage #1: 1.4-dibromobenzene; trimethylsilylacetylene With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran Sonogashira coupling; Inert atmosphere; Stage #2: With potassium hydroxide In methanol | 72% |
Sonogashira Cross-Coupling; |
1,4-diethynylbenzene
Conditions | Yield |
---|---|
at 750℃; for 1.5h; Pyrolysis; | 72% |
2-methyl-4-(4-(3-methyl-3-((2-nitrobenzyl)oxy)but-1-yn-1-yl)phenyl)but-3-yn-2-ol
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With potassium hydroxide In toluene at 110℃; for 12h; Inert atmosphere; UV-irradiation; | 70% |
tert-butyldimethyl((4-((trimethylsilyl)ethynyl)phenyl)ethynyl)silane
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With potassium trimethylsilonate In dimethyl sulfoxide at 70℃; for 12h; Sealed tube; Schlenk technique; | 70% |
1,4-bis(1,2-dibromoethyl)benzene
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With potassium hydroxide; Aliquat 336 In xylene Heating; | 63% |
With potassium hydroxide | |
With potassium tert-butylate In tert-butyl alcohol for 1h; Heating; |
dimethylmonochlorosilane
(4-bromophenyl)(trimethylsilyl)acetylene
A
1,4-diethynylbenzene
B
(p-(dimethylsilyl)phenyl)acetylene
Conditions | Yield |
---|---|
Stage #1: (4-bromophenyl)(trimethylsilyl)acetylene With potassium carbonate In methanol for 5h; Stage #2: With n-butyllithium In tetrahydrofuran at -78℃; Stage #3: dimethylmonochlorosilane In tetrahydrofuran | A n/a B 63% |
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 80℃; for 0.5h; | 41% |
1,4-diethynylcyclohexa-2,5-diene-1,4-diol
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With acetic acid; tin(ll) chloride at 40 - 45℃; | |
With tin(ll) chloride In acetic acid |
trans-1,4-diethynyl-1,4-dihydroxy-2,5-cyclohexadiene
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With sulfuric acid; tin(ll) chloride |
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With sulfuric acid; tin(ll) chloride |
1,4-di(1-chloroethenyl)benzene
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With sodium amide In ammonia for 7h; Yield given; |
A
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With sodium hydroxide Ambient temperature; Yields of byproduct given; | |
With sodium hydroxide Ambient temperature; Yield given; |
2,2'-bis-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-1,1'-p-phenylene-bis-ethanone
A
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With sodium hydroxide; trichlorophosphate 1. dioxane, 80 degC, 4h; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; copper(l) iodide 2.) toluene, 100 deg C; Multistep reaction; |
1.4-dibromobenzene
propargyl alcohol
A
4-bromo-1-ethynylbenzene
B
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With manganese(IV) oxide; potassium hydroxide; copper diacetate; diisopropylamine; triphenylphosphine; palladium dichloride 1.) reflux, 3 h, 2.) CH2Cl2, Et2O, 90 min; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃; | |
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 110℃; |
1,4-bis(1,2-dibromoethyl)benzene
1,4-diethynylbenzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper(I) iodide; diisopropylamine; triethylamine / dichlorobis(triphenylphosphine)palladium(II) / tetrahydrofuran / 96 h / 60 °C 2: aq. potassium hydroxide / tetrahydrofuran; methanol / 1 h View Scheme | |
Multi-step reaction with 2 steps 1: 81 percent / TBAF / tetrahydrofuran View Scheme | |
Multi-step reaction with 2 steps 1: 93 percent / CuI; diisopropylamine / Pd(PPh3)4 / toluene / 24 h / 50 °C 2: 92 percent / K2CO3 / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: phenylacetylene With triphenylvinyllithium; triphenylphosphine; [(nbd)RhCl]2 In diethyl ether; toluene at 30℃; for 0.5h; Stage #2: 1,4-diethynylbenzene In diethyl ether; toluene at 30℃; for 0.166667h; | 100% |
1,4-diethynylbenzene
4-bromo-benzaldehyde
4,4'-(1,4-phenylenebis(ethyne-2,1-diyl))dibenzaldehyde
Conditions | Yield |
---|---|
With triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran for 30h; Sonogashira coupling; Heating; | 100% |
1-Bromo-2-iodobenzene
1,4-diethynylbenzene
1,4-bis((2-bromophenyl)ethynyl)benzene
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) Sonogashira Cross-Coupling; | 100% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile at 80℃; for 12h; Sonogashira coupling; Inert atmosphere; | 99% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile at 80℃; for 12h; Sonogashira coupling; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With copper(II) sulfate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In water; acetone; tert-butyl alcohol at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
With aluminum oxide; N-iodo-succinimide In acetonitrile at 80℃; for 1h; Molecular sieve; | 99% |
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve; | 98% |
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve; | 98% |
trans-dichloro-bis(tri-n-butylphosphine)platinum(II)
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With copper(l) iodide; diethylamine In tetrahydrofuran refluxed under N2; pptd., concd., dried (vac.), dissolved in CHCl3, poured into MeOH; | 99% |
2-iodoprop-2-en-1-ol
1,4-diethynylbenzene
4,4'-(1,4-phenylene)bis(2-methylenebut-3-yn-1-ol)
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 65℃; for 16h; Sonogashira coupling; Inert atmosphere; | 99% |
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 20℃; for 12h; Sonogashira Cross-Coupling; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1,4-diethynylbenzene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2–(3-phenylpropiolyl)benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 6h; Inert atmosphere; Stage #3: With hydrogenchloride In water at 20℃; for 3h; Inert atmosphere; | 98.8% |
Conditions | Yield |
---|---|
With copper(l) iodide; di-n-propylamine; bis-triphenylphosphine-palladium(II) chloride at 75℃; for 0.666667h; | 98% |
4-acetoxyiodobenzene
1,4-diethynylbenzene
1,4-bis(4-acetoxyphenyl)ethynylbenzene
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 18h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With copper(I) (2-biphenyl)di-tert-butylphosphane-aniline hexaflurophosphate In toluene at 50℃; under 1500.15 Torr; Reagent/catalyst; Solvent; Time; Inert atmosphere; | A n/a B 98% |
1,4-diethynylbenzene
benzyl chloride
1-benzyl-4-(4-ethynylphenyl)-1H-1,2,3-triazole
Conditions | Yield |
---|---|
With sodium azide In water at 20℃; for 2h; Huisgen Cycloaddition; Green chemistry; | 98% |
4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide
1,4-diethynylbenzene
Conditions | Yield |
---|---|
With tris(triphenylphosphine)rhodium(I) chloride In acetone at 25℃; for 20h; | 97% |
Conditions | Yield |
---|---|
With sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; water; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water Inert atmosphere; | 97% |
1,4-diethynylbenzene
8-bromoguanosine
8,8'-[benzene-1,4-diyl-di(ethyn-2,1-diyl)]diguanosine
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 70℃; for 16h; Sonogashira-Hagihara coupling; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With C16H20Cl2N2O2Pd; potassium hydroxide In water; acetonitrile at 20℃; for 1h; Sonogashira Cross-Coupling; | 97% |
With 2,2′-(1,2-phenylene)bis(4,4-di-methyl-4,5-dihydrooxazole)-N,N′-dichloridopalladium(II); potassium hydroxide In water; acetonitrile at 20℃; for 1h; Sonogashira Cross-Coupling; | 97% |
With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; silica gel for 0.333333h; Sonogashira coupling; Neat (no solvent); ball mill; chemoselective reaction; | 69 %Spectr. |
1,4-diethynylbenzene
1,4-di(1H-1,2,3-triazol-4-yl)benzene
Conditions | Yield |
---|---|
With sodium azide In water at 100℃; Green chemistry; regioselective reaction; | 97% |
With copper(l) iodide; trimethylsilylazide In methanol; N,N-dimethyl-formamide at 90℃; for 44h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
In dichloromethane (N2); addn. of acetylene deriv. to CH2Cl2 suspn. of triphenylphosphine-borane deriv., stirring overnight; concg., layering with pentane, cooling to -35°C overnight, isolation of ppt., elem. anal.; | 97% |
In dichloromethane Inert atmosphere; | 97% |
3-iodopyridine
1,4-diethynylbenzene
1,4-bis(pyridin-3-ylethynyl)benzene
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 50℃; for 48h; Sonogashira coupling; | 97% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 18h; Sonogashira coupling; Inert atmosphere; | 65% |
1,4-diethynylbenzene
ortho-bromobenzaldehyde
2,2'-(1,4-phenylenebis(ethyne-2,1-diyl))dibenzaldehyde
Conditions | Yield |
---|---|
Stage #1: ortho-bromobenzaldehyde With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Sonogashira Cross-Coupling; Stage #2: 1,4-diethynylbenzene With copper(l) iodide In tetrahydrofuran at 20℃; for 24h; Sonogashira Cross-Coupling; | 97% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile at 80℃; for 18h; Sonogashira coupling; Inert atmosphere; | 80% |
trimethylsilyl iodide
1,4-diethynylbenzene
1,4-Bis(trimethylsilylethynyl)benzene
Conditions | Yield |
---|---|
With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine In toluene at 80℃; for 24h; Inert atmosphere; | 97% |
1,4-diethynylbenzene
benzyl bromide
1-benzyl-4-(4-(1-benzyl-1H-1,2,3-triazole-4-yl)phenyl)-1H-1,2,3-triazole
Conditions | Yield |
---|---|
With sodium azide; [CuI(3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane)3] In water; acetonitrile at 125℃; for 0.25h; Catalytic behavior; Huisgen Cycloaddition; Sealed tube; Microwave irradiation; | 97% |
With sodium azide; [(tris(3,5-dimethyl-1-pyrazolyl)methane)2Cu](BF4)2 In methanol; water at 125℃; for 0.5h; Catalytic behavior; Microwave irradiation; | 95% |
With sodium azide In water at 40℃; for 3h; | 89% |
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In water; benzene for 1h; | 96.5% |
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