(2-(3-methylphenyl)ethynyl)trimethylsilane
1-ethynyl-3-methyl-benzene
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
1-(bromo-ethynyl)-3-methyl-benzene
1-ethynyl-3-methyl-benzene
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
1-ethynyl-3-methyl-benzene
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; toluene at 140℃; | 72% |
1-(1,1-Dichloro-ethyl)-3-methyl-benzene
1-ethynyl-3-methyl-benzene
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Heating; | 46% |
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 |
Conditions | Yield |
---|---|
Multistep reaction; |
methanol
Methyl fluoride
phenylacetylene
A
1-Phenylprop-1-yne
B
1-ethynyl-2-methylbenzene
C
1-ethynyl-3-methyl-benzene
D
2-Methylacetophenone
E
4-n-methylphenylacetylene
Conditions | Yield |
---|---|
at 37℃; under 700 Torr; Product distribution; Mechanism; Irradiation; various concentration of substrates, addition of various amounts of NEt3; |
Methyl fluoride
phenylacetylene
A
1-Phenylprop-1-yne
B
1-ethynyl-2-methylbenzene
C
1-ethynyl-3-methyl-benzene
D
4-n-methylphenylacetylene
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
1-ethynyl-3-methyl-benzene
Conditions | Yield |
---|---|
(i) EtMgBr, (ii) KOH; Multistep reaction; |
1-(3-tolyl)-3,3-diethoxyprop-1-yne
1-ethynyl-3-methyl-benzene
Conditions | Yield |
---|---|
(i) aq. CF3CO2H, (ii) NaOMe; Multistep reaction; |
Butadiyne
toluene
A
1-ethynyl-2-methylbenzene
B
1-ethynyl-3-methyl-benzene
C
4-n-methylphenylacetylene
Conditions | Yield |
---|---|
Alkylation; Irradiation; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N; CuI / Pd(PPh3)4 / Heating 2: K2CO3 / methanol / 20 °C View Scheme |
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 |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 84 percent / PCl5 / 12 h / 20 °C 2: 46 percent / KOH / ethanol / Heating View Scheme |
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; |
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
m-tolyl aldehyde
1-ethynyl-3-methyl-benzene
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 60℃; for 0.75h; Seyferth-Gilbert Homologation; Microwave irradiation; |
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. |
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; |
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
1-ethynyl-3-methyl-benzene
4-(m-tolylethynyl)tetrahydro-2H-pyran-4-ol
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% |
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. |
Conditions | Yield |
---|---|
With copper(II) sulfate; sodium L-ascorbate In water at 20℃; Reagent/catalyst; Solvent; | 100% |
1-ethynyl-3-methyl-benzene
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% |
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
(E)-3,3'-(but-1-en-3-yne-1,4-diyl)bis(methylbenzene)
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
1-ethynyl-3-methyl-benzene
2-m-tolyl-1-o-tolylethyne
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
ethyl-3,3,3-trifluoropyruvate
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
benzoyl(3,4-dihydroisoquinolinium-2-yl)azanide
C25H22N2O
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
1-(azidomethyl)-3-bromobenzene
1-(3-bromobenzyl)-4-(3-methylphenyl)-1H-1,2,3-triazole
Conditions | Yield |
---|---|
With Octanoic acid; C27H31AgNO3P In toluene at 20℃; for 48h; Inert atmosphere; regioselective reaction; | 99% |
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
1-ethynyl-3-methyl-benzene
1-methyl-3-(2-phenylethynyl)benzene
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
1-ethynyl-3-methyl-benzene
1,1,1-trifluoro-2-phenyl-4-(m-tolyl)but-3-yn-2-ol
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; |
Conditions | Yield |
---|---|
With 2,2,2-Trifluoroacetophenone; triphenylphosphine In water at 60℃; for 2h; Schlenk technique; Inert atmosphere; Green chemistry; | 99% |
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
iodobenzene
1-ethynyl-3-methyl-benzene
1-phenyl-3-(3-methylphenyl)prop-2-yn-1-one
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
1-ethynyl-3-methyl-benzene
Conditions | Yield |
---|---|
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 24h; | 99% |
1-ethynyl-3-methyl-benzene
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
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% |
Conditions | Yield |
---|---|
With C54H56N8Ru(2+)*2F6P(1-); triethylamine In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction; | 99% |
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
Conditions | Yield |
---|---|
With sodium L-ascorbate In methanol at 25℃; for 16h; Inert atmosphere; Schlenk technique; | 99% |
1-ethynyl-3-methyl-benzene
1-iodo-2-((2-methylallyl)oxy)benzene
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% |
Conditions | Yield |
---|---|
In toluene at 70℃; for 12h; Inert atmosphere; Molecular sieve; | 99% |
1-ethynyl-3-methyl-benzene
1-iodo-2-((2-methylallyl)oxy)benzene
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
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
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
Conditions | Yield |
---|---|
With samarium diiodide In tetrahydrofuran at 55℃; for 0.75h; Inert atmosphere; | 99% |
1-ethynyl-3-methyl-benzene
benzyl azide
1-benzyl-4-(3-methylphenyl)-1H-1,2,3-triazole
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
1-ethynyl-3-methyl-benzene
(Z)-N-(3-m-tolylprop-2-ynylidene)cyclohexanamine
Conditions | Yield |
---|---|
With C29H51NO2Si2Y In benzene at 20℃; for 2h; Inert atmosphere; stereoselective reaction; | 98% |
The IUPAC name of 3-Ethynyltoluene is 1-ethynyl-3-methylbenzene. With the CAS registry number 766-82-5, it is also named as 3-Methylphenylacetylene. The product's categories are Acetylenes; Acetylenic Hydrocarbons; Alkynes; Organic Building Blocks; Terminal. It is clear light yellow to brown liquid which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.86; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.86; (4)ACD/LogD (pH 7.4): 2.86; (5)ACD/BCF (pH 5.5): 87.83; (6)ACD/BCF (pH 7.4): 87.83; (7)ACD/KOC (pH 5.5): 856.8; (8)ACD/KOC (pH 7.4): 856.8; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.534; (13)Molar Refractivity: 38.43 cm3; (14)Molar Volume: 123.6 cm3; (15)Polarizability: 15.23×10-24 cm3; (16)Surface Tension: 35.3 dyne/cm; (17)Enthalpy of Vaporization: 39.57 kJ/mol; (18)Vapour Pressure: 1.48 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 116.0626; (21)MonoIsotopic Mass: 116.0626; (22)Heavy Atom Count: 9; (23)Complexity: 126.
Preparation of 3-Ethynyltoluene: It can be obtained by 1-(1,1-dichloro-ethyl)-3-methyl-benzene. This reaction needs reagent KOH and solvent ethanol by heating. The yield is 46%.
Uses of 3-Ethynyltoluene: It can react with 2-trimethylsilanylethynyl-benzaldehyde to get 3-m-tolyl-1-(2-trimethylsilanylethynyl-phenyl)-prop-2-yn-1-ol. This reaction needs reagent n-BuLi and solvent tetrahydrofuran at temperature of 0 °C. The yield is 54%.
When you are using this chemical, please be cautious about it as the following:
It is flammable, so people should keep it away from sources of ignition. It is also irritating to eyes, respiratory system and skin. And it may cause lung damage if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES:C#Cc1cccc(c1)C
2. InChI:InChI=1/C9H8/c1-3-9-6-4-5-8(2)7-9/h1,4-7H,2H3
3. InChIKey:RENYIDZOAFFNHC-UHFFFAOYAT
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