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206490 Sigma-Aldrich

4-Ethynylanisole

97%

Synonym: 1-Ethynyl-4-methoxybenzene

  • CAS Number 768-60-5

  • Linear Formula CH3OC6H4C≡CH

  • Molecular Weight 132.16

  •  MDL number MFCD00168815

  •  PubChem Substance ID 24852402

  •  NACRES NA.22

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Properties

Related Categories Alkynes, Building Blocks, Chemical Synthesis, Organic Building Blocks, Terminal More...
assay   97%
refractive index   n20/D 1.563 (lit.)
bp   87-91 °C/11 mmHg (lit.)
mp   28-29 °C (lit.)
density   1.019 g/mL at 25 °C (lit.)
SMILES string   COc1ccc(cc1)C#C
InChI   1S/C9H8O/c1-3-8-4-6-9(10-2)7-5-8/h1,4-7H,2H3
InChI key   KBIAVTUACPKPFJ-UHFFFAOYSA-N

Description

General description

4-Ethynylanisole forms the corresponding propargyl aldehyde in good yield directly from DMF-dimethyl acetal without the need for making an acetylide salt. 1,3-dipolar cycloaddition of acceptor-cyclopropylmethylsilanes affords functionalized cyclopentenes in good yields.

Application

4-Ethynylanisole was used:
• in the synthesis of photoluminescent 1,2-dihydrophosphinines via a [4 + 2] cycloaddition
• along with an arylboronic acid and sodium azide in a copper-catalyzed, three-component synthesis of trisubstituted 1,2,4-triazoles
• in a study of a gold (III)-catalyzed hydroamination of alkynes leading to N-vinylindoles.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
179.6 °F - closed cup
Flash Point(C) 
82 °C - closed cup

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Protocols & Articles

Articles

Pd(PhCN)2Cl2/P(t-Bu)3: A Versatile Catalyst for Sonogashira Reactions of Aryl Bromides at Room Temperature

The Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles using precatalysts P1 or P2 is reported. The procedure allows for the reaction of variously substituted indazole, benzimid...
Keywords: Catalysis, Chromatography, Column chromatography, Coupling reactions, Cross couplings

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Alkynes and Acetylenic Building Blocks

We list over 600 alkyne building blocks, including a wide array of propargyl alcohols, acetylenic boron reagents, and halogenated substrates for cross-coupling. Additionally, many of these are termin...
Keywords: Building blocks, Coupling reactions, Cross couplings

Peer-Reviewed Papers
15

References

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