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206490

Sigma-Aldrich

4-Ethynylanisole

97%

Synonym(s):

1-Ethynyl-4-methoxybenzene

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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
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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]. 1,3-dipolar cycloaddition of acceptor-cyclopropylmethylsilanes affords functionalized cyclopentenes in good yields[2].

4-Ethynylanisole can be used as a building block in organic synthesis and also used in sonogashira coupling reactions. [3]

Application

1,3-dipolar cycloaddition of acceptor-cyclopropylmethylsilanes affords functionalized cyclopentenes in good yields.[2]
4-Ethynylanisole was used:
  • in the synthesis of photoluminescent 1,2-dihydrophosphinines via a [4 + 2] cycloaddition[4]
  • along with an arylboronic acid and sodium azide in a copper-catalyzed, three-component synthesis of trisubstituted 1,2,4-triazoles[5]
  • in a study of a gold (III)-catalyzed hydroamination of alkynes leading to N-vinylindoles[6].
Forms the corresponding propargyl aldehyde in good yield directly from DMF-dimethyl acetal without the need for making an acetylide salt.[1]

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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Certificates of Analysis (COA)

Lot/Batch Number
0000216382
0000178671
0000208290
BGBC3249V
BGBC1528V

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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].
Synlett, 278-278 (2007)
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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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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