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206490

Sigma-Aldrich

4-Ethynylanisole

97%

Synonyme(s) :

1-Ethynyl-4-methoxybenzene

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About This Item

Formule linéaire :
CH3OC6H4C≡CH
Numéro CAS:
768-60-5
Poids moléculaire :
132.16
Numéro MDL:
MFCD00168815
Code UNSPSC :
12352100
ID de substance PubChem :
24852402
Nomenclature NACRES :
NA.22
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Essai

97%

Forme

solid

Indice de réfraction

n20/D 1.563 (lit.)

pb

87-91 °C/11 mmHg (lit.)

Pf

28-29 °C (lit.)

Densité

1.019 g/mL at 25 °C (lit.)

Chaîne SMILES 

COc1ccc(cc1)C#C

InChI

1S/C9H8O/c1-3-8-4-6-9(10-2)7-5-8/h1,4-7H,2H3

Clé InChI

KBIAVTUACPKPFJ-UHFFFAOYSA-N

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Description générale

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]

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

179.6 °F - closed cup

Point d'éclair (°C)

82 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000216382
0000178671
0000208290
BGBC3249V
BGBC1528V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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)
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].
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
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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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