766-82-5

Basic information

• Product Name: 3-Ethynyltoluene
• Synonyms: m-Ethylnyltoluene;3-Ethynyltoluene, 1-Ethynyl-3-methylbenzene;M-Tolylacetylene, 97% 1GR;1-Ethynyl-3-methylbenzene m-Tolylacetylene;3-Ethynyltoluene 97%;Benzene,1-ethynyl-3-methyl-;3'-METHYLPHENYL ACETYLENE;3-ETHYNYLTOLUENE
• CAS NO: 766-82-5
• Molecular Formula: C₉H₈
• Molecular Weight: 116.16
• EINECS: -0
• Product Categories: Acetylenes;Acetylenic Hydrocarbons;Alkynes;Organic Building Blocks;Terminal
• Mol File: 766-82-5.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 170-175 °C(lit.)
• Flash Point: 50°C
• Appearance: Clear light yellow to brown/Liquid
• Density: 0.900 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.48mmHg at 25°C
• Refractive Index: n20/D 1.5440(lit.)
• Storage Temp.: Flammables area
• BRN: 2038007
• CAS DataBase Reference: 3-Ethynyltoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethynyltoluene(766-82-5)
• EPA Substance Registry System: 3-Ethynyltoluene(766-82-5)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38-65
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 766-82-5(Hazardous Substances Data)

Usage

Uses

3-ETHYNYLTOLUENE is a useful research chemical.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 358, 1978 DOI: 10.1021/jo00396a046Tetrahedron Letters, 13, p. 5209, 1972

InChI:InChI=1/C9H8/c1-3-9-6-4-5-8(2)7-9/h1,4-7H,2H3

Synthetic route

(2-(3-methylphenyl)ethynyl)trimethylsilane (40230-90-8) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
With potassium carbonate In methanol at 25℃; for 3h;	93%
With potassium trimethylsilonate In dimethyl sulfoxide at 60℃; under 760.051 Torr; for 7h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;	93%
With potassium carbonate In methanol; dichloromethane for 1h; Inert atmosphere;	72%

N-methylmethane sulphonamide (1184-85-6) + 1-(bromo-ethynyl)-3-methyl-benzene (33675-43-3) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate; toluene at 80℃; Inert atmosphere;	90%

2-methyl-4-(3'-methylphenyl)but-3-yn-2-ol (63079-66-3) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
With potassium hydroxide In methanol; toluene at 140℃;	72%

1-(1,1-Dichloro-ethyl)-3-methyl-benzene (16035-10-2) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
With potassium hydroxide In ethanol Heating;	46%

3-Iodotoluene (625-95-6) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
	37%
Multi-step reaction with 2 steps 1: dimethylformamide / 160 °C 2: (i) EtMgBr, (ii) KOH View Scheme
Multi-step reaction with 2 steps 1: (i) nBuLi, (ii) CuI, (iii) /BRN= 1903634/ 2: (i) aq. CF3CO2H, (ii) NaOMe View Scheme

acetaldehyde (75-07-0) + m-tolylmagnesium bromide (28987-79-3) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
Multistep reaction;

methanol (67-56-1) + Methyl fluoride (593-53-3) + phenylacetylene (536-74-3) → 1-Phenylprop-1-yne (673-32-5) + 1-ethynyl-2-methylbenzene (766-47-2) + 1-ethynyl-3-methyl-benzene (766-82-5) + 2-Methylacetophenone (577-16-2, 122382-54-1) + 4-n-methylphenylacetylene (766-97-2)

Conditions	Yield
at 37℃; under 700 Torr; Product distribution; Mechanism; Irradiation; various concentration of substrates, addition of various amounts of NEt3;

Methyl fluoride (593-53-3) + phenylacetylene (536-74-3) → 1-Phenylprop-1-yne (673-32-5) + 1-ethynyl-2-methylbenzene (766-47-2) + 1-ethynyl-3-methyl-benzene (766-82-5) + 4-n-methylphenylacetylene (766-97-2)

Conditions	Yield
at 37℃; under 700 Torr; Product distribution; Mechanism; Irradiation; various concentration of substrates, addition of various amounts of NEt3;

1-phenyl-3-(3-methylphenyl)prop-2-yn-1-one (14674-99-8) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
(i) EtMgBr, (ii) KOH; Multistep reaction;

1-(3-tolyl)-3,3-diethoxyprop-1-yne (62358-87-6) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
(i) aq. CF3CO2H, (ii) NaOMe; Multistep reaction;

Butadiyne (460-12-8) + toluene (108-88-3) → 1-ethynyl-2-methylbenzene (766-47-2) + 1-ethynyl-3-methyl-benzene (766-82-5) + 4-n-methylphenylacetylene (766-97-2)

Conditions	Yield
Alkylation; Irradiation;

meta-bromotoluene (591-17-3) → 1-ethynyl-3-methyl-benzene (766-82-5) + Co2(CO)8

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N; CuI / Pd(PPh3)4 / Heating 2: K2CO3 / methanol / 20 °C View Scheme

meta-bromotoluene (591-17-3) + amalgamated aluminium → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / Et3N, pyridine, Ph3P, CuI / (Ph3P)2PdCl2 / 7 h / Heating 2: 72 percent / KOH / toluene; methanol / 140 °C View Scheme

3-Methylacetophenone (585-74-0) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / PCl5 / 12 h / 20 °C 2: 46 percent / KOH / ethanol / Heating View Scheme

meta-bromotoluene (591-17-3) + trimethylsilylacetylene (1066-54-2) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
Stage #1: meta-bromotoluene; trimethylsilylacetylene With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In acetonitrile at 60℃; for 16h; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 2h;

meta-bromotoluene (591-17-3) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: bis(triphenylphosphine)palladium(II) dichloride; copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 2: potassium carbonate / methanol / 3 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / Inert atmosphere 2: potassium carbonate / methanol / 3 h / 20 °C / Inert atmosphere View Scheme

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + m-tolyl aldehyde (620-23-5) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
With potassium carbonate In methanol at 60℃; for 0.75h; Seyferth-Gilbert Homologation; Microwave irradiation;

3-Iodotoluene (625-95-6) + acetylene (74-86-2) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In dimethylsulfoxide-d6 at 20℃; for 2h; Sonogashira Cross-Coupling;	86 %Chromat.

trimethylsilylacetylene (1066-54-2) + 1-halo-3-methylbenzene → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
Stage #1: trimethylsilylacetylene; 1-halo-3-methylbenzene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 12h; Inert atmosphere; Stage #2: With potassium carbonate In methanol for 2h;

3-Iodotoluene (625-95-6) + trimethylsilylacetylene (1066-54-2) → 1-ethynyl-3-methyl-benzene (766-82-5)

Conditions	Yield
Stage #1: 3-Iodotoluene; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: With methanol; potassium carbonate at 20℃; for 3h; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere;

Tetrahydro-4H-pyran-4-one (29943-42-8) + 1-ethynyl-3-methyl-benzene (766-82-5) → 4-(m-tolylethynyl)tetrahydro-2H-pyran-4-ol (1435770-36-7)

Conditions	Yield
Stage #1: 1-ethynyl-3-methyl-benzene With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.0833333h; Stage #2: With lithium bromide In tetrahydrofuran; hexane at 20℃; for 0.5h; Stage #3: Tetrahydro-4H-pyran-4-one In tetrahydrofuran; hexane at -78 - 20℃; for 0.666667h;	100%

1-ethynyl-3-methyl-benzene (766-82-5) + HSiPh3 (789-25-3) → (E)-(3-methylstyryl)triphenylsilane

Conditions	Yield
With C24H23ClCrIrNO3 In 1,1,2,2-tetrachloroethane at 40℃; for 2h; Inert atmosphere; Schlenk technique; regioselective reaction;	100%
With C77H70N2OPtSi2 In toluene at 40℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; stereoselective reaction;	99 %Chromat.

Methyl azidoacetate (1816-92-8) + 1-ethynyl-3-methyl-benzene (766-82-5) → methyl 2-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)acetate

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In water at 20℃; Reagent/catalyst; Solvent;	100%

1-ethynyl-3-methyl-benzene (766-82-5) → 1,4-bis(3-methylphenyl)-1,3-butadiyne

Conditions	Yield
With CuO-Fe3O4; potassium tert-butylate; oxygen at 60℃; for 72h; Glaser Coupling;	99%
With copper(l) iodide; oxygen; benzylamine In neat (no solvent) at 20℃; under 760.051 Torr; for 12h; Green chemistry;	99%
With sodium acetate; silver sulfate In dimethyl sulfoxide at 90℃; for 11h;	99%

2-Iodophenol (533-58-4) + 1-ethynyl-3-methyl-benzene (766-82-5) → 2‐m‐tolylbenzofuran (92724-29-3)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 3h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;	99%
With potassium phosphate; C45H51Cl4N7Pd2 In dimethyl sulfoxide at 90℃; for 16h; Reagent/catalyst; Schlenk technique;	93%
With potassium phosphate In N,N-dimethyl-formamide at 160℃; Schlenk technique; Inert atmosphere; Glovebox; Green chemistry;	87%

1-ethynyl-3-methyl-benzene (766-82-5) → (E)-3,3'-(but-1-en-3-yne-1,4-diyl)bis(methylbenzene) (1133321-55-7)

Conditions	Yield
With [{Pd(μ-OH)Cl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)}2]; potassium hydroxide In ethanol at 22℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; stereoselective reaction;	99%
With C77H74N2OPtSi2 In toluene at 60℃; Reagent/catalyst; Inert atmosphere; diastereoselective reaction;	95%
With Wilkinson's catalyst; sodium dodecyl-sulfate In water; toluene at 50℃; for 15h;	83%

ortho-methylphenyl iodide (615-37-2) + 1-ethynyl-3-methyl-benzene (766-82-5) → 2-m-tolyl-1-o-tolylethyne (205529-19-7)

Conditions	Yield
With potassium carbonate; copper(II) oxide In dimethyl sulfoxide at 160℃; for 12h; Sonogashira coupling; Inert atmosphere;	99%
With C17H32Cl2N4OPd; potassium carbonate In ethanol at 80℃; for 1h; Sonogashira Cross-Coupling;	89%

1-ethynyl-3-methyl-benzene (766-82-5) + ethyl-3,3,3-trifluoropyruvate (13081-18-0) → ethyl 2-hydroxy-4-m-tolyl-2-(trifluoromethyl)but-3-ynoate

Conditions	Yield
With [Rh{(S,S)-4-NO2-Phebox-Bn}(OAc)2]*H2O In diethyl ether at 25℃; for 24h; Inert atmosphere; enantioselective reaction;	99%

1-ethynyl-3-methyl-benzene (766-82-5) + benzoyl(3,4-dihydroisoquinolinium-2-yl)azanide (42046-26-4) → C25H22N2O (1337924-72-7)

Conditions	Yield
With copper diacetate; 2,6-bis[(4R)-5,5-dihydro-4-phenyl-2-oxazolyl]pyridine In dichloromethane at 0℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

1-ethynyl-3-methyl-benzene (766-82-5) + 1-(azidomethyl)-3-bromobenzene (126799-86-8) → 1-(3-bromobenzyl)-4-(3-methylphenyl)-1H-1,2,3-triazole (1361946-54-4)

Conditions	Yield
With Octanoic acid; C27H31AgNO3P In toluene at 20℃; for 48h; Inert atmosphere; regioselective reaction;	99%

methanesulfonic acid (75-75-2) + 1-ethynyl-3-methyl-benzene (766-82-5) → C10H12O3S

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine In 1,2-dichloro-ethane at 70℃; for 2h; regioselective reaction;	99%
With immobilized Wilkinson’s complex, RhCl(PPh3)3 supported on (diphenylphosphine) In 1,2-dichloro-ethane at 70℃; for 24h; stereoselective reaction;	92%

bromobenzene (108-86-1) + 1-ethynyl-3-methyl-benzene (766-82-5) → 1-methyl-3-(2-phenylethynyl)benzene (14635-91-7)

Conditions	Yield
With water; potassium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Catalytic behavior; Sonogashira Cross-Coupling;	99%
With tetrabutylammomium bromide; sodium acetate In dimethyl sulfoxide at 120℃; for 40h; Sonogashira Cross-Coupling; Inert atmosphere;	89%

1,1,1-trifluoroacetophenone (434-45-7) + 1-ethynyl-3-methyl-benzene (766-82-5) → 1,1,1-trifluoro-2-phenyl-4-(m-tolyl)but-3-yn-2-ol (1590442-96-8)

Conditions	Yield
With C42H62AgN4(1+)*BF4(1-) In water at 60℃; for 15h;	99%
With triphenylphosphine In water at 60℃; for 2h; Schlenk technique; Inert atmosphere; Green chemistry;	97%
With copper diacetate; potassium carbonate In dimethyl sulfoxide at 70℃; for 24h; Temperature;	97%
With copper(I) oxide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 24h;	68%
With C54H56N8Ru(2+)*2F6P(1-); triethylamine In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;

1-ethynyl-3-methyl-benzene (766-82-5) + 2,6-dichlorobenzaldehyde (83-38-5) → C16H12Cl2O (1590443-25-6)

Conditions	Yield
With 2,2,2-Trifluoroacetophenone; triphenylphosphine In water at 60℃; for 2h; Schlenk technique; Inert atmosphere; Green chemistry;	99%

piperidine (110-89-4) + 1-ethynyl-3-methyl-benzene (766-82-5) + benzaldehyde (100-52-7) → C21H23N

Conditions	Yield
With Cu(at)MOF-5-C In toluene at 110℃; for 6h; Inert atmosphere;	99%
With [copper(I)]2[(2-picolyliminomethyl)pyrrole]2 In toluene at 110℃; for 2h; Inert atmosphere;	98%
With silver carbonate In neat (no solvent) at 110℃; for 0.916667h;	96%
With cycloaurated phosphinothioicamide gold(III) complex immobilized in a silica-supported ionic liquid In neat (no solvent) at 60℃; for 8h; Green chemistry;

formic acid (64-18-6) + iodobenzene (591-50-4) + 1-ethynyl-3-methyl-benzene (766-82-5) → 1-phenyl-3-(3-methylphenyl)prop-2-yn-1-one (14674-99-8)

Conditions	Yield
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine In toluene at 30℃; Inert atmosphere; Sealed tube;	99%
With triethylamine; dicyclohexyl-carbodiimide In toluene at 30℃; for 24h; Inert atmosphere;	96%
With palladium diacetate; acetic anhydride; triethylamine; triphenylphosphine In toluene at 30℃; Sonogashira Cross-Coupling; Inert atmosphere;	82%
With iodine; palladium diacetate; triethylamine; triphenylphosphine In toluene at 40℃; for 4h; Sonogashira Cross-Coupling; Sealed tube;	82%

2-azido-1-(piperidin-1-yl)ethan-1-one (1132647-39-2) + 1-ethynyl-3-methyl-benzene (766-82-5) → 1-(piperidin-1-yl)-2-(4-m-tolyl-1H-1,2,3-triazol-1-yl)ethanone

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 24h;	99%

1-benzylisatin + 1-ethynyl-3-methyl-benzene (766-82-5) → 1-benzyl-3-hydroxy-3-(m-tolylethynyl)indolin-2-one

Conditions	Yield
With C42H62AgN4(1+)*BF4(1-) In methanol; water at 60℃; for 15h;	99%
With C30H22N4O2Rh(1+)*F6P(1-) In tetrahydrofuran at 50℃; Schlenk technique; Sealed tube;	92%
With potassium tert-butylate In toluene at 20℃; Inert atmosphere;	48%

1-ethynyl-3-methyl-benzene (766-82-5) → 1-(3-chlorobenzyl)-4-(m-tolyl)-1H-1,2,3-triazole

Conditions	Yield
With (1,3-bis(2,6-dimethylphenyl)thiourea)Cu(Cl)(1,3-bis(2,6-dimethylphenyl)thiourea) In neat (no solvent) at 20℃; for 1.5h;	99%

1,1,1-trifluoroacetophenone (434-45-7) + 1-ethynyl-3-methyl-benzene (766-82-5) → (S)-1,1,1-trifluoro-2-phenyl-4-(m-tolyl)but-3-yn-2-ol

Conditions	Yield
With C54H56N8Ru(2+)*2F6P(1-); triethylamine In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	99%

1-ethynyl-3-methyl-benzene (766-82-5) + Ethyl propionate (105-37-3) → 1-(m-tolyl)pent-1-yn-3-one

Conditions	Yield
Stage #1: 1-ethynyl-3-methyl-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Ethyl propionate With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃;	99%

1-ethynyl-3-methyl-benzene (766-82-5) + 4-(4-azidophenoxy)-N-methylpicolinamide → N-methyl-4-(4-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)phenoxy)picolinamide

Conditions	Yield
With sodium L-ascorbate In methanol at 25℃; for 16h; Inert atmosphere; Schlenk technique;	99%

1-ethynyl-3-methyl-benzene (766-82-5) + 1-iodo-2-((2-methylallyl)oxy)benzene (156642-47-6) → 3-methyl-3-[3-(3-methylphenyl)prop-2-ynyl]-2,3-dihydro-1-benzofuran

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.25h; Microwave irradiation; Inert atmosphere; Sealed tube; Green chemistry;	99%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; Schlenk technique;	95%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + 1-ethynyl-3-methyl-benzene (766-82-5) + benzaldehyde (100-52-7)

Conditions	Yield
In toluene at 70℃; for 12h; Inert atmosphere; Molecular sieve;	99%

1-ethynyl-3-methyl-benzene (766-82-5) + 1-iodo-2-((2-methylallyl)oxy)benzene (156642-47-6) → (R)-3-methyl-3-(3-(m-tolyl)prop-2-yn-1-yl)-2,3-dihydrobenzofuran

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; (R)-N-((S)-(3,5-di-tert-butyl-4-methoxyphenyl)(2-(dicyclohexylphosphanyl)phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide In ethyl acetate at 80℃; Inert atmosphere; Sealed tube; enantioselective reaction;	99%

+ 1-ethynyl-3-methyl-benzene (766-82-5) → ethyl (E)-2,2-difluoro-4-iodo-4-(m-tolyl)but-3-enoate

Conditions	Yield
With diethylzinc In hexane; acetonitrile at -20℃; for 16h; Schlenk technique; Inert atmosphere; stereoselective reaction;	99%
With dimanganese decacarbonyl In cyclohexane at 20℃; for 1h; Schlenk technique; Irradiation;	95%

1-ethynyl-3-methyl-benzene (766-82-5) → 3,3″-dimethyl-4'-(m-tolyl)-1,1':2′,1″-terphenyl

Conditions	Yield
With 9,10-diphenylanthracene; N-ethyl-N,N-diisopropylamine; iron(II) chloride In acetonitrile for 1h; Sealed tube; Irradiation; regioselective reaction;	99%

1-ethynyl-3-methyl-benzene (766-82-5) → rac-(4,4-dimethyl-2-(m-tolyl)cyclopent-2-en-1-yl)(o-tolyl)methanone

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 55℃; for 0.75h; Inert atmosphere;	99%

1-ethynyl-3-methyl-benzene (766-82-5) + benzyl azide (622-79-7) → 1-benzyl-4-(3-methylphenyl)-1H-1,2,3-triazole (1044501-72-5)

Conditions	Yield
With Cu/Fe In dichloromethane at 30℃; for 8h;	98%
With porous cross-linked polymer-phenanthroline-supported copper catalyst In water at 20℃; for 0.666667h; Huisgen Cycloaddition;	98%
With (1,3-bis(2,6-dimethylphenyl)thiourea)Cu(Cl)(1,3-bis(2,6-dimethylphenyl)thiourea) In neat (no solvent) at 20℃; for 1.5h;	98%

Cyclohexyl isocyanide (931-53-3) + 1-ethynyl-3-methyl-benzene (766-82-5) → (Z)-N-(3-m-tolylprop-2-ynylidene)cyclohexanamine (1114547-94-2)

Conditions	Yield
With C29H51NO2Si2Y In benzene at 20℃; for 2h; Inert atmosphere; stereoselective reaction;	98%

Upstream product

• 62358-87-6 1-(3-tolyl)-3,3-diethoxyprop-1-yne 
• 460-12-8 Butadiyne 
• 108-88-3 toluene 
• 625-95-6 3-Iodotoluene 
• 1066-54-2 trimethylsilylacetylene 
• 1184-85-6 N-methylmethane sulphonamide 
• 33675-43-3 1-(bromo-ethynyl)-3-methyl-benzene 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 620-23-5 m-tolyl aldehyde 
• 591-17-3 meta-bromotoluene 
• 585-74-0 3-Methylacetophenone 
• 14674-99-8 1-phenyl-3-(3-methylphenyl)prop-2-yn-1-one 
• 63079-66-3 2-methyl-4-(3'-methylphenyl)but-3-yn-2-ol 
• 16035-10-2 1-(1,1-Dichloro-ethyl)-3-methyl-benzene 

Downstream Products

• 33649-34-2 2,4,6-Trinitro-benzenesulfonic acid (E)-2-phenylsulfanyl-1-m-tolyl-vinyl ester 
• 32117-57-0 Triethyl-(4-m-tolyl-buta-1,3-diynyl)-silane 
• 33649-38-6 2,4,6-Trinitro-benzenesulfonic acid (E)-2-(4-chloro-phenylsulfanyl)-1-m-tolyl-vinyl ester 
• 33675-43-3 1-(bromo-ethynyl)-3-methyl-benzene 
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Relevant articles and documents

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

BF3·OEt2-Promoted Propargyl Alcohol Rearrangement/[1,5]-Hydride Transfer/Cyclization Cascade Affording Tetrahydroquinolines

An efficient BF3·OEt2-mediated propargyl alcohol rearrangement/[1,5]-hydride transfer/cyclization cascade for the synthesis of tetrahydroquinoline derivatives has been described. The substituents adjacent to triple bonds play an important role in the formation of ketones (via [1,3]-hydroxyl shift) or alkenyl fluorides which are products of formal trans-carbofluorination of internal alkynes. This method provides a rapid access to diverse heterocycles in moderate to excellent yields.

A practical non-metal catalytic silicon of the amino protection of the new method (by machine translation)

The invention relates to a high efficiency, mild organic silicon reagent carbon silicon key fracture of the new method. The method of this reaction to the alkali is cheap and easy to obtain metal catalyst, in order to common commercial solvent as a reaction solvent and a hydrogen source, in the air and in the under mild conditions can be successfully catalytic trimethyl aryl silicon reagent or aryl alkyne base silicon reagent selectively generating carbon silicon key cracking hydrogenation reaction, the substrate universality is wide, functional group compatibility outstanding. The first innovative to realize the non-transition metal catalyzed carbon silicon key breaking reaction, also overcome the traditional method requires the use of greatly excessive inorganic alkali or an expensive metal catalyst to the limitation of the silicon of the amino protection, for the laboratory preparation and industry in the production of the organosilicon group deprotection provides a completely new strategy. (by machine translation)