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766-47-2

766-47-2

Identification

  • Product Name:Benzene,1-ethynyl-2-methyl-

  • CAS Number: 766-47-2

  • EINECS:

  • Molecular Weight:116.163

  • Molecular Formula: C9H8

  • HS Code:2902909090

  • Mol File:766-47-2.mol

Synonyms:Toluene,o-ethynyl- (6CI,7CI,8CI); (2-Methylphenyl)acetylene; (2-Methylphenyl)ethyne;(o-Methylphenyl)acetylene; 1-Ethynyl-2-methylbenzene; 2-Ethynyltoluene;2-Tolylacetylene; o-Tolylacetylene

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Safety information and MSDS view more

  • Pictogram(s):

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:2-Methylphenylacetylene
  • Packaging:50mg
  • Price:$ 45
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Methylphenylacetylene 97%
  • Packaging:25 g
  • Price:$ 712
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Methylphenylacetylene 97%
  • Packaging:1 g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Methylphenylacetylene 97%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Ethynyltoluene 97%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Ethynyltoluene 97%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Methylphenylacetylene 95+%
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  • Manufacture/Brand:Matrix Scientific
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  • Product Description:2-Ethynyltoluene
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  • Manufacture/Brand:Apolloscientific
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Relevant articles and documentsAll total 41 Articles be found

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

Sattler, Lars E.,Hilt, Gerhard

supporting information, p. 605 - 608 (2020/12/07)

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.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Biletskyi, Bohdan,Kong, Lingyu,Tenaglia, Alphonse,Clavier, Hervé

supporting information, p. 2578 - 2585 (2021/03/18)

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea

Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block

Varga, Bálint,Tóth, Balázs L.,Béke, Ferenc,Csenki, János T.,Kotschy, András,Novák, Zoltán

supporting information, p. 4925 - 4929 (2021/07/01)

A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.

Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with: N -substituted pyrroles

Guo, Jing,Cheong, Odelia,Bamford, Karlee L.,Zhou, Jiliang,Stephan, Douglas W.

supporting information, p. 1855 - 1858 (2020/02/22)

Metal-free hydroarylation of alkynes with N-substituted pyrroles is shown to be most efficiently mediated by B(C6F5)3 to yield 12 variants of dipyrrole-alkanes, a mono-hydroarylation product and a tetrahydroarylation produ

Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes

Lasányi, Dániel,Tolnai, Gergely L.

supporting information, p. 10057 - 10062 (2019/12/24)

Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.

Process route upstream and downstream products

Process route

methanol
67-56-1

methanol

Methyl fluoride
593-53-3

Methyl fluoride

phenylacetylene
536-74-3

phenylacetylene

1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

1-ethynyl-3-methyl-benzene
766-82-5

1-ethynyl-3-methyl-benzene

2-Methylacetophenone
577-16-2,122382-54-1

2-Methylacetophenone

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

Conditions
Conditions Yield
at 37 ℃; under 700 Torr; Product distribution; Mechanism; Irradiation; various concentration of substrates, addition of various amounts of NEt3;
1-(1-bromovinyl)-2-methylbenzene
74346-22-8

1-(1-bromovinyl)-2-methylbenzene

1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

2-Methylacetophenone
577-16-2,122382-54-1

2-Methylacetophenone

Conditions
Conditions Yield
With methanol; water; at 88 ℃; Product distribution; Rate constant;
Methyl fluoride
593-53-3

Methyl fluoride

phenylacetylene
536-74-3

phenylacetylene

1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

1-ethynyl-3-methyl-benzene
766-82-5

1-ethynyl-3-methyl-benzene

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

Conditions
Conditions Yield
at 37 ℃; under 700 Torr; Product distribution; Mechanism; Irradiation; various concentration of substrates, addition of various amounts of NEt3;
1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

1-ethynyl-3-methyl-benzene
766-82-5

1-ethynyl-3-methyl-benzene

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

Conditions
Conditions Yield
Irradiation;
trimethyl[(2-methylphenyl)ethynyl]silane
3989-15-9

trimethyl[(2-methylphenyl)ethynyl]silane

1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

Conditions
Conditions Yield
With potassium trimethylsilonate; In dimethyl sulfoxide; at 60 ℃; for 7h; under 760.051 Torr; Reagent/catalyst; Solvent; Catalytic behavior; Sealed tube;
87%
With potassium carbonate; In methanol; at 20 ℃; for 3h;
82%
With methanol; potassium carbonate; at 20 ℃;
80%
With potassium carbonate; In methanol; dichloromethane; for 1h; Inert atmosphere;
70%
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;
53%
With potassium fluoride; In methanol;
29%
trimethyl[(2-methylphenyl)ethynyl]silane; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;
With ammonium chloride; Inert atmosphere;
23%
(alkaline hydrolysis);
With tetrabutyl ammonium fluoride; In tetrahydrofuran; water; at 20 ℃;
2.00 g
With potassium carbonate; In methanol;
trimethyl[(2-methylphenyl)ethynyl]silane; With methanol; potassium hydroxide; at 0 ℃;
With hydrogenchloride; water; In methanol;
With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.5h;
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;
With methanol; potassium carbonate; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere; Schlenk technique;
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;
1.96 g
With potassium fluoride; at 20 ℃; for 16h; Reagent/catalyst; Temperature;
With potassium fluoride; In tetrahydrofuran; methanol; at 20 ℃; for 1h; Inert atmosphere;
With potassium carbonate; In methanol;
With potassium carbonate; In methanol; at 20 ℃; for 2h;
With copper(l) iodide; fluorosilicic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; at 60 ℃; for 2h;
With potassium carbonate; In methanol; at 20 ℃;
With potassium fluoride; In methanol; at 20 ℃; for 24h; Sealed tube;
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

Propiolic acid
471-25-0

Propiolic acid

1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

Conditions
Conditions Yield
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane; In dimethyl sulfoxide; at 0 - 60 ℃; for 5h; Sealed flask;
48%
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

Conditions
Conditions Yield
ortho-methylphenyl iodide; trimethylsilylacetylene; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine; In toluene; at 25 ℃; for 16.0833h; Inert atmosphere;
With water; potassium hydroxide; In methanol; toluene; at 25 ℃; for 3h; Inert atmosphere;
With potassium carbonate; In methanol; acetonitrile; at 40 ℃;
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

Conditions
Conditions Yield
45%
Multi-step reaction with 2 steps
1: dimethylformamide / 160 °C
2: (i) EtMgBr, (ii) KOH
In N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0 - 20 °C
2: methanol; potassium carbonate / 20 °C
With methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; triethylamine;
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere; Schlenk technique
2: potassium carbonate; methanol / dichloromethane / 12 h / 20 °C / Inert atmosphere; Schlenk technique
With methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; 1: |Sonogashira Cross-Coupling;
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; copper(l) chloride; triethylamine / dimethyl sulfoxide / 1 h / 20 °C / Inert atmosphere
2: potassium fluoride / 16 h / 20 °C
With bis-triphenylphosphine-palladium(II) chloride; potassium fluoride; triethylamine; copper(l) chloride; In dimethyl sulfoxide; 1: |Sonogashira Cross-Coupling;
Multi-step reaction with 2 steps
1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 20 °C
2: potassium carbonate / methanol
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; 1: |Sonogashira Cross-Coupling;
Multi-step reaction with 2 steps
1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 0 - 20 °C
2: potassium carbonate / methanol / 20 °C
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; triethylamine; In methanol;
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / Inert atmosphere
2: potassium carbonate / methanol; dichloromethane / 1 h / Inert atmosphere
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1: |Sonogashira Cross-Coupling;
Multi-step reaction with 2 steps
1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 1 h / 50 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling;
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / 1 h / 60 °C / Sealed tube
2: potassium fluoride / methanol / 24 h / 20 °C / Sealed tube
With bis-triphenylphosphine-palladium(II) chloride; potassium fluoride; copper(l) iodide; N-ethyl-N,N-diisopropylamine; In methanol;
2-Methylacetophenone
577-16-2,122382-54-1

2-Methylacetophenone

1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

Conditions
Conditions Yield
With Nonafluorobutanesulfonyl fluoride; tert-butylimino-tri(pyrrolidino)phosphorane; In N,N-dimethyl-formamide; at 20 ℃; for 19h;
77%
With phosphorus pentachloride; ammonia; sodium amide; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: 72 percent / PCl5 / 12 h / 20 °C
2: 45 percent / KOH / ethanol / Heating
With potassium hydroxide; phosphorus pentachloride; In ethanol;
phenylacetylene
536-74-3

phenylacetylene

methyl iodide
74-88-4

methyl iodide

1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

Conditions
Conditions Yield
With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; at -60 - -50 ℃;
88%
With n-butyllithium; potassium tert-butylate; Yield given. Multistep reaction; 1) THF, hexane, -40 deg C, 2) THF, hexane, -70 to 5 deg C, 3) THF, hexane, -30 to 15 deg C;

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