206490

4-Ethynylanisole

97%

• Synonym(s): 1-Ethynyl-4-methoxybenzene
• Linear Formula: CH₃OC₆H₄C≡CH
• CAS Number: 768-60-5
• Molecular Weight: 132.16
• MDL number: MFCD00168815
• UNSPSC Code: 12352100
• PubChem Substance ID: 24852402
• NACRES: NA.22

Properties

• assay: 97%
• form: solid
• 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.

4-Ethynylanisole can be used as a building block in organic synthesis and also used in sonogashira coupling reactions.

Application

1,3-dipolar cycloaddition of acceptor-cyclopropylmethylsilanes affords functionalized cyclopentenes in good yields.

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.

Forms the corresponding propargyl aldehyde in good yield directly from DMF-dimethyl acetal without the need for making an acetylide salt.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: 179.6 °F - closed cup
• flash_point_c: 82 °C - closed cup
• ppe: Eyeshields, Gloves, type N95 (US)