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Sigma-Aldrich

4-Ethynylanisole

97%

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

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tetrahedron Letters, 45, 5043-5043 (2004)
Formal [3+2] addition of acceptor-substituted cyclopropylmethylsilanes with aryl acetylenes.
Veejendra K Yadav et al.
Angewandte Chemie (International ed. in English), 43(20), 2669-2671 (2008-07-17)
Yuhua Zhang et al.
Organic letters, 9(4), 627-630 (2007-02-09)
A highly efficient double-hydroamination reaction of o-alkynylanilines with terminal alkynes leading to N-alkenylindoles was developed by using gold(III) as a catalyst under neat conditions. [reaction: see text].
Laura C Pavelka et al.
Dalton transactions (Cambridge, England : 2003), 41(11), 3294-3301 (2012-01-31)
The addition of 4-trifluoromethyl-1-ethynylbenzene, phenylacetylene, or 4-ethynylanisole to P-mesityldiphenylmethylenephosphine, 1, produced photoluminescent 1,2-dihydrophosphinines 4a-c, respectively, in quantitative yield via a [4 + 2] cycloaddition. Limited reactivity was observed between 1 and non-aromatic alkynes. P-[Bis(trimethylsilyl)amino][(trimethylsilyl)methylene]phosphine, 2, and P-mesityl[(t-butyl)(trimethylsiloxy)methylene]phosphine, 3, showed extremely
Resorcinol--formaldehyde resins as metal-free semiconductor photocatalysts for solar-to-hydrogen peroxide energy conversion
Shiraishi, Yasuhiro and Takii, et al.
Nature Materials, 18, 985-993 (2019)
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