113705-27-4

Basic information

• Product Name: Naphthalene, 2,7-diethynyl
• Synonyms: Naphthalene, 2,7-diethynyl
• CAS NO: 113705-27-4
• Molecular Formula: C₁₄H₈
• Molecular Weight: 176.21332
• Mol File: 113705-27-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 315.2±15.0 °C(Predicted)
• Appearance: /
• Density: 1.10±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Naphthalene, 2,7-diethynyl(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene, 2,7-diethynyl(113705-27-4)
• EPA Substance Registry System: Naphthalene, 2,7-diethynyl(113705-27-4)

Safety Data

• Hazardous Substances Data: 113705-27-4(Hazardous Substances Data)

Usage

General Description

Naphthalene, 2,7-diethynyl is a chemical compound that consists of carbon and hydrogen atoms. It is a derivative of naphthalene, a polycyclic aromatic hydrocarbon. The compound is primarily used in organic synthesis and as a building block in the production of various organic compounds. Its alkyne functional groups make it a valuable reagent for the formation of carbon-carbon bonds in chemical reactions. It is also being studied for its potential applications in materials science and pharmaceutical research. Due to its high reactivity and potential health hazards, proper handling and storage precautions are necessary when working with naphthalene, 2,7-diethynyl.

Synthetic route

2,7-bis[2-(trimethylsilyl)ethynyl]naphthalene (113705-17-2) → 2,7-diethynylnaphthalene (113705-27-4)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 2h;	100%
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 2h;	100%
With potassium fluoride dihydrate In tetrahydrofuran; methanesulfonic acid Concentration; Time;	100%

2,7-dibromonaphthalene (58556-75-5) → 2,7-diethynylnaphthalene (113705-27-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / (PhCN)2PdCl2, Ph3P, copper(II) acetate hydrate, diisopropylamine / 1.) RT, 4 h, 2.) reflux, 1 h 2: 91 percent / KOH, H2O / methanol / 0.33 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 40 °C / Inert atmosphere 2: potassium carbonate / tetrahydrofuran; methanol / 0.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 65 °C 2: potassium fluoride dihydrate / tetrahydrofuran; methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; copper(l) iodide; diisopropylamine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere 2: potassium hydroxide; water / tetrahydrofuran View Scheme

2,7-Dihydroxynaphthalene (582-17-2) + 2-oxy-benzaldehyde → 2,7-diethynylnaphthalene (113705-27-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) bromine, Ph3P / 1.) acetonitrile, 70 deg C, 30 min, 2.) 250 deg C, 50 min 2: 82 percent / (PhCN)2PdCl2, Ph3P, copper(II) acetate hydrate, diisopropylamine / 1.) RT, 4 h, 2.) reflux, 1 h 3: 91 percent / KOH, H2O / methanol / 0.33 h / Ambient temperature View Scheme

2,7-Dihydroxynaphthalene (582-17-2) → 2,7-diethynylnaphthalene (113705-27-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: dmap; 2,6-dimethylpyridine / dichloromethane; tetrahydrofuran / 7.25 h / -78 - 0 °C / Molecular sieve; Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; piperidine / Molecular sieve; Inert atmosphere; Reflux 3: sodium hydroxide / tetrahydrofuran; water / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: dmap; 2,6-dimethylpyridine / dichloromethane; tetrahydrofuran / 7.25 h / -78 - 0 °C / Molecular sieve; Inert atmosphere 2: piperidine; triphenylphosphine / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / Inert atmosphere; Molecular sieve; Reflux 3: sodium hydroxide; water / tetrahydrofuran / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 40 °C / Inert atmosphere; Sealed tube 3: potassium carbonate; methanol / 24 h / 20 °C View Scheme

methanesulfonic acid 1,1,1-trifluoro-1,1'-(2,7-naphthalenedidyl) ester (151391-00-3) → 2,7-diethynylnaphthalene (113705-27-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; piperidine / Molecular sieve; Inert atmosphere; Reflux 2: sodium hydroxide / tetrahydrofuran; water / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: piperidine; triphenylphosphine / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / Inert atmosphere; Molecular sieve; Reflux 2: sodium hydroxide; water / tetrahydrofuran / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 40 °C / Inert atmosphere; Sealed tube 2: potassium carbonate; methanol / 24 h / 20 °C View Scheme

methyl 3-iodo-7-isopropylazulene-1-carboxylate (1086430-30-9) + 2,7-diethynylnaphthalene (113705-27-4) → C44H36O4

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 50℃; Sonogashira Cross-Coupling;	99%

9-azido-9H-xanthene + 2,7-diethynylnaphthalene (113705-27-4) → 4-(7-ethynylnaphthalen-2-yl)-1-(9H-xanthen-9-yl)-1H-1,2,3-triazole + 2,7-bis(1-(9H-xanthen-9-yl)-1H-1,2,3-triazol-4-yl)naphthalene

Conditions	Yield
With sodium L-ascorbate; N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 50℃;	A 69% B 96%

3-iodopyridine (1120-90-7) + 2,7-diethynylnaphthalene (113705-27-4) → 2,7-bis(pyridin-3-ylethynyl)naphthalene (1262535-58-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 18h; Sonogashira coupling; Inert atmosphere;	76%

C14H11IN4 + 2,7-diethynylnaphthalene (113705-27-4) → C42H28N8

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 50℃; for 24h; Sealed tube; Inert atmosphere;	50%

di-tert-butyl (((5-azido-1,3-phenylene)bis(oxy))bis(propane-3,1-diyl))dicarbamate (1443619-95-1) + 2,7-diethynylnaphthalene (113705-27-4) → C58H78N10O12 (1448431-93-3) + C36H43N5O6 (1448431-96-6)

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 16h;	A 43% B 41%

p-nitrobenzene iodide (636-98-6) + 2,7-diethynylnaphthalene (113705-27-4) → 2,7-bis((4-nitrophenyl)ethynyl)naphthalene (1426232-31-6)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; Sonogashira Cross-Coupling; Inert atmosphere;	36%

2,7-diethynylnaphthalene (113705-27-4) + chloro-diphenylphosphine (1079-66-9) → 2,7-bis[(diphenylphosphoryl)ethynyl]naphthalene

Conditions	Yield
Stage #1: 2,7-diethynylnaphthalene With n-butyllithium In methanol; diethyl ether; nitrogen at -80 - -20℃; for 3h; liquid N2; Stage #2: chloro-diphenylphosphine In methanol; diethyl ether; nitrogen at -80 - 20℃; for 24h; liquid N2; Stage #3: With dihydrogen peroxide In dichloromethane for 2h; Cooling with ice;	27.6%
Stage #1: 2,7-diethynylnaphthalene With n-butyllithium In diethyl ether at -80 - -10℃; for 3h; Inert atmosphere; Stage #2: chloro-diphenylphosphine In diethyl ether at -80 - 20℃; Inert atmosphere; Stage #3: With dihydrogen peroxide In dichloromethane; water at 0℃; for 3h;	3.6 g

Dimethylphenylsilane (766-77-8) + 2,7-diethynylnaphthalene (113705-27-4) → (Z,Z)-2,7-bis[2-(dimethyl(phenyl)silyl)ethenyl]naphthalene

Conditions	Yield
With diphosphinidenecyclobutene-coordinated ruthenium In dichloromethane at 20℃; for 0.5h;

2,7-diethynylnaphthalene (113705-27-4) → (Z,Z)-2,7-bis(2-bromoethenyl)naphthalene

Conditions	Yield
Multi-step reaction with 2 steps 1: diphosphinidenecyclobutene-coordinated ruthenium complex / CH2Cl2 / 0.5 h / 20 °C 2: 59 percent / N-bromosuccinimide / acetonitrile; H2O / 2 h / 0 °C View Scheme

N-(3-azidophenyl)-2-(pyrrolidin-1-yl)acetamide (1262546-38-2) + 2,7-diethynylnaphthalene (113705-27-4) → C38H38N10O2 (1400645-91-1)

Conditions	Yield
With copper(ll) sulfate pentahydrate; bathophenanthrolinedispufonic acid disodium salt; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;

N-(3-azidophenyl)-2-(piperidin-1-yl)acetamide (1262546-35-9) + 2,7-diethynylnaphthalene (113705-27-4) → C40H42N10O2 (1400645-89-7)

Conditions	Yield
With copper(ll) sulfate pentahydrate; bathophenanthrolinedispufonic acid disodium salt; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;

N-(3-azidophenyl)-2-(diethylamino)acetamide (1262546-34-8) + 2,7-diethynylnaphthalene (113705-27-4) → C38H42N10O2 (1401242-86-1)

Conditions	Yield
With copper(ll) sulfate pentahydrate; bathophenanthrolinedispufonic acid disodium salt; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;
copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;	100 %Chromat.

N-(4-azido-phenyl)-2-(pyrrolidin-1-yl)-acetamide (921201-87-8) + 2,7-diethynylnaphthalene (113705-27-4) → C38H38N10O2 (1400645-92-2)

Conditions	Yield
With copper(ll) sulfate pentahydrate; bathophenanthrolinedispufonic acid disodium salt; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;

N-(4-azido-phenyl)-2-diethylamino-acetamide (921201-89-0) + 2,7-diethynylnaphthalene (113705-27-4) → C38H42N10O2 (1400645-95-5)

Conditions	Yield
With copper(ll) sulfate pentahydrate; bathophenanthrolinedispufonic acid disodium salt; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;

pyrrolidine (123-75-1) + N-(3-azidophenyl)-3-(pyrrolidin-1-yl)propanamide (1070978-77-6) + 2,7-diethynylnaphthalene (113705-27-4) → C40H42N10O2 (1400645-90-0)

Conditions	Yield
With copper(ll) sulfate pentahydrate; bathophenanthrolinedispufonic acid disodium salt; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;

N-(3-azidophenyl)-3-(diethylamino)propanamide (1262546-37-1) + 2,7-diethynylnaphthalene (113705-27-4) + diethylamine (109-89-7) → C40H46N10O2 (1400645-94-4)

Conditions	Yield
With copper(ll) sulfate pentahydrate; bathophenanthrolinedispufonic acid disodium salt; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;

pyrrolidine (123-75-1) + N-(4-azido-phenyl)-3-(pyrrolidin-1-yl)-propionamide (921201-92-5) + 2,7-diethynylnaphthalene (113705-27-4) → C40H42N10O2 (1400645-93-3)

Conditions	Yield
With copper(ll) sulfate pentahydrate; bathophenanthrolinedispufonic acid disodium salt; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;

N-(4-azidophenyl)-3-(diethylamino)propanamide (1262546-36-0) + 2,7-diethynylnaphthalene (113705-27-4) + diethylamine (109-89-7) → C40H46N10O2 (1400645-96-6)

Conditions	Yield
With copper(ll) sulfate pentahydrate; bathophenanthrolinedispufonic acid disodium salt; sodium L-ascorbate In water; tert-butyl alcohol at 110℃; for 0.25h; Microwave irradiation;

C22H35BrN2O6 (1382469-16-0) + 2,7-diethynylnaphthalene (113705-27-4) → C38H44N4O4 (1443620-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 70 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 3 h View Scheme

C22H35BrN2O6 (1382469-16-0) + 2,7-diethynylnaphthalene (113705-27-4) → C58H76N4O12 (1443620-23-2)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 70℃; for 18h; Sonogashira Cross-Coupling; Inert atmosphere;	0.36 g

A (1500081-63-9) + 2,7-diethynylnaphthalene (113705-27-4) → C42H52N12 (1454655-66-3)

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 120℃; for 0.25h; Microwave irradiation;

A (1500081-64-0) + 2,7-diethynylnaphthalene (113705-27-4) → C42H52N12 (1454655-67-4)

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 120℃; for 0.25h; Microwave irradiation;

tert-butyl (3-(3-azidophenoxy)propyl)carbamate (1443619-93-9) + 2,7-diethynylnaphthalene (113705-27-4) → C32H32N8O2*2C2HF3O2

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 16 h / 20 °C 2: dichloromethane / 3 h / 20 °C View Scheme

tert-butyl (3-(3-azidophenoxy)propyl)carbamate (1443619-93-9) + 2,7-diethynylnaphthalene (113705-27-4) → C42H48N8O6 + C28H28N4O3

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 16h;

di-tert-butyl (((4-azido-1,2-phenylene)bis(oxy))bis(propane-3,1-diyl))dicarbamate (1443619-94-0) + 2,7-diethynylnaphthalene (113705-27-4) → 4C2HF3O2*C38H46N10O4

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 16 h / 20 °C 2: dichloromethane / 3 h / 20 °C View Scheme

Upstream product

• 113705-17-2 2,7-bis[2-(trimethylsilyl)ethynyl]naphthalene 
• 151391-00-3 methanesulfonic acid 1,1,1-trifluoro-1,1'-(2,7-naphthalenedidyl) ester 
• 582-17-2 2,7-Dihydroxynaphthalene 
• 58556-75-5 2,7-dibromonaphthalene 

Downstream Products

• 1400645-91-1 C₃₈H₃₈N₁₀O₂ 
• 1400645-89-7 C₄₀H₄₂N₁₀O₂ 
• 1401242-86-1 C₃₈H₄₂N₁₀O₂ 
• 1400645-92-2 C₃₈H₃₈N₁₀O₂ 
• 1400645-95-5 C₃₈H₄₂N₁₀O₂ 
• 1400645-90-0 C₄₀H₄₂N₁₀O₂ 
• 1400645-94-4 C₄₀H₄₆N₁₀O₂ 
• 1400645-93-3 C₄₀H₄₂N₁₀O₂ 
• 1400645-96-6 C₄₀H₄₆N₁₀O₂ 
• 1426232-31-6 2,7-bis((4-nitrophenyl)ethynyl)naphthalene 
• 1448431-93-3 C₅₈H₇₈N₁₀O₁₂ 
• 1448431-96-6 C₃₆H₄₃N₅O₆ 
• 1454655-67-4 C₄₂H₅₂N₁₂ 

Relevant articles and documents

2-(1,2,3-Triazol-4-yl)pyridine-containing ethynylarenes as selective 'turn-on' fluorescent chemosensors for Ni(II)

A series of ethynylarene compounds containing 2-(1,2,3-triazol-4-yl)pyridine chelating units were studied as fluorescent chemosensors for metal cations in aqueous solution. Analogs possessing two chelating units bridged by either 1,4-diethynylphenyl or 2,7-diethynylnaphthyl subunits displayed large hypsochromic shifts coupled with signal intensification when exposed to increasing concentrations of Ni(II), a unique response among 22 metal cation analytes. This response was shown to be reversible, and is proposed to derive from disruption of aggregate formation upon Ni(II) binding at the peripheral chelating units.

Unique solvent-dependent fluorescence of nitro-group-containing naphthalene derivatives with weak donor-strong acceptor system

We synthesized nitro-group-containing π-conjugated naphthalene derivatives with a weak donor-strong acceptor system and investigated their photophysical properties. The nitro group was introduced into naphthalene through the phenyl or phenylethynyl moiety at the C2 and C7 positions as the strong acceptor moiety, and a methoxy group was introduced into naphthalene directly at the position opposite to the nitro group, as a weak donor moiety. While 2-(4-nitrophenyl)naphthalene did not show fluorescence in various solvents, 2-methoxy-6-(4-nitrophenyl)naphthalene showed fluorescence in weakly polar solvents (ΦF = 0.11 in CH2Cl2), with a large Stokes shift (Δν = 12,000 cm-1). Additionally, 2-methoxy-6-(4-nitrophenyl)naphthalene did not show fluorescence in polar solvents (acetonitrile) and non-polar solvents (toluene). This unique solvent-dependent fluorescence is remarkable for environmental fluorescence sensor applications.

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