Skip to Content
MilliporeSigma
All Photos(3)

Documents

206490

Sigma-Aldrich

4-Ethynylanisole

97%

Synonym(s):

1-Ethynyl-4-methoxybenzene

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

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

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

wgk_germany

WGK 3

flash_point_f

179.6 °F

flash_point_c

82 °C

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 8

1 of 8

1-Bromo-4-ethynylbenzene 97%

Sigma-Aldrich

206512

1-Bromo-4-ethynylbenzene

4-tert-Butylphenylacetylene 96%

Sigma-Aldrich

593001

4-tert-Butylphenylacetylene

4-Ethynyl-N,N-dimethylaniline 97%

Sigma-Aldrich

592609

4-Ethynyl-N,N-dimethylaniline

1-Ethynyl-4-methoxy-2-methylbenzene 97%

Sigma-Aldrich

521191

1-Ethynyl-4-methoxy-2-methylbenzene

2-Ethynyltoluene 97%

Sigma-Aldrich

558788

2-Ethynyltoluene

3-Chloro-1-ethynylbenzene 97%

Sigma-Aldrich

630268

3-Chloro-1-ethynylbenzene

4-(Trifluoromethoxy)phenylacetylene 97%

Sigma-Aldrich

672858

4-(Trifluoromethoxy)phenylacetylene

1-Ethynyl-4-phenoxybenzene 97%

Sigma-Aldrich

521213

1-Ethynyl-4-phenoxybenzene

Synlett, 278-278 (2007)
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)
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
Tetrahedron Letters, 45, 5043-5043 (2004)
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].
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service