100516-61-8

Basic information

• Product Name: hexaethynylbenzene
• Synonyms: hexaethynylbenzene;1,2,3,4,5,6-Hexaethynylbenzene
• CAS NO: 100516-61-8
• Molecular Formula: C₁₈H₆
• Molecular Weight: 222.24024
• Mol File: 100516-61-8.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 382.4±42.0 °C(Predicted)
• Appearance: /
• Density: 1.14±0.1 g/cm3(Predicted)
• CAS DataBase Reference: hexaethynylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: hexaethynylbenzene(100516-61-8)
• EPA Substance Registry System: hexaethynylbenzene(100516-61-8)

Safety Data

• Hazardous Substances Data: 100516-61-8(Hazardous Substances Data)

Usage

General Description

Hexaethynylbenzene is a chemical compound with the molecular formula C18H6. It consists of a benzene ring with six ethynyl (C≡C) groups attached to it. Hexaethynylbenzene is a highly conjugated aromatic compound with interesting electronic and optical properties. It has been studied for its potential applications in materials science and organic electronics, as well as for its use in molecular electronics and nanotechnology. Its unique structure and properties make it an intriguing molecule for further research and potential technological advancements.

Synthetic route

1,2,3,4,5,6-hexa(2-trimethylsilylethynyl)benzene (100516-62-9) → 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8)

Conditions	Yield
With potassium fluoride In 1,2-dimethoxyethane at 0℃; for 2.5h;	99%
With potassium fluoride; 18-crown-6 ether In 1,2-dimethoxyethane at 23℃;
With potassium fluoride; 18-crown-6 ether In 1,2-dimethoxyethane at 23℃; for 0.5h; Hydrolysis;

2-Methyl-4-[pentakis-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-but-3-yn-2-ol (70603-27-9) → 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol

hexabromobenzene (87-82-1) + trimethylsilylacetylene (1066-54-2) → 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8)

Conditions	Yield
With potassium fluoride; copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; 18-crown-6 ether 1.) 100 deg C, 72 h; 2.) glyme, 10 min; Yield given. Multistep reaction;

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → 1,2,3,4,5,6-hexa(2-chloroethynyl)benzene

Conditions	Yield
With N-chloro-succinimide; tetrabutyl-ammonium chloride; silver carbonate In acetonitrile at 20℃; for 12h;	63%

iodobenzene (591-50-4) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → Hexakis(phenylethynyl)benzene (110846-75-8)

Conditions	Yield
With copper(l) iodide; triethylamine; bis(triphenylphosphane)palladium(II) In 1,2-dimethoxyethane at 60℃; for 68h; Sonogashira cross coupling;	41%

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) + Bis(trimethylsilyl)ethyne (14630-40-1) → 2,3,6,7,10,11-hexakis(trimethylsilyl)starphenylene (102234-00-4)

Conditions	Yield
dicarbonylcyclopentadienylcobalt for 19.5h; Heating;	39%

1,6-Bis(triisopropylsilyl)-1,3,5-hexatriyne (111409-80-4) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → C90H132Si6

Conditions	Yield
cyclopentadienyl-biscarbonyl-cobalt(I) In toluene for 16h; Heating; Irradiation; Yield given;

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) + 2,5-dihydroxy-2,5-dimethyl-3-hexyne (142-30-3) → C42H48O6

Conditions	Yield
With dicarbonylcyclopentadienylcobalt In xylene for 8h; Cycloaddition; Heating; Irradiation;

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) + dihexyl 6-bromoazulene-1,3-dicarboxylate (501123-88-2) → hexakis[1,3-bis(hexyloxycarbonyl)-6-azulenylethynyl]benzene

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran for 18h; Sonogashira-Hagihara coupling; Heating;	214 mg

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) + 4',5'-bis(butylthio)-4-iodotetrathiafulvalene (717918-81-5) → hexakis(4',5'-bis(butylthio)tetrathiafulvalenylethenyl)benzene

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 5h; Sonogashira coupling;	143 mg

4'-(4-iodo-2,6-dimethylphenyl)-2,2':6',2''-terpyridine (908563-58-6) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → hexakis[3,5-dimethyl-1,4-(2,2':6',2''-terpyridine-4'-yl)phenylethynyl]benzene

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 20 - 80℃; for 48h; Sonogashira coupling;	262 mg

3,4,3',4'-tetrabutyl-5''-iodo-5-phenyl-[2,2';5',2'']terthiophene (1255382-94-5) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → hexakis[2-(3',4',3'',4''-tetrabutyl-5''-phenyl-[5,2';5',2'']terthienyl)ethynyl]benzene (1255382-84-3)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; Sonogashira coupling;	175 mg

2-iodo-3-[(trimethylsilyl)ethynyl]naphthalene (1404452-60-3) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → hexakis(2-{3-[(trimethylsilyl)ethynyl]naphthyl}ethynyl)benzene (1404452-61-4)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 45 - 80℃; for 65h; Sonogashira Cross-Coupling; Inert atmosphere;	36.2 mg

1-iodo-2-[(trimethylsilyl)ethynyl]naphthalene (1404452-66-9) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → hexakis(1-{2-[(trimethylsilyl)ethynyl]naphthyl}ethynyl)benzene (1404452-64-7)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 45 - 85℃; for 120h; Sonogashira Cross-Coupling; Inert atmosphere;	92.3 mg

Upstream product

• 70603-27-9 2-Methyl-4-[pentakis-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-but-3-yn-2-ol 
• 87-82-1 hexabromobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 100516-62-9 1,2,3,4,5,6-hexa(2-trimethylsilylethynyl)benzene 

Downstream Products

• 110846-75-8 Hexakis(phenylethynyl)benzene 

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