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206490

Sigma-Aldrich

4-Ethynylanisole

97%

Sinonimo/i:

1-Ethynyl-4-methoxybenzene

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About This Item

Formula condensata:
CH3OC6H4C≡CH
Numero CAS:
768-60-5
Peso molecolare:
132.16
Numero MDL:
MFCD00168815
Codice UNSPSC:
12352100
ID PubChem:
24852402
NACRES:
NA.22

Saggio

97%

Stato

solid

Indice di rifrazione

n20/D 1.563 (lit.)

P. ebollizione

87-91 °C/11 mmHg (lit.)

Punto di fusione

28-29 °C (lit.)

Densità

1.019 g/mL at 25 °C (lit.)

Stringa SMILE

COc1ccc(cc1)C#C

InChI

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

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Descrizione generale

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.

Applicazioni

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

179.6 °F - closed cup

Punto d’infiammabilità (°C)

82 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BGBC3249V
BGBC1528V
BGBB6527V
BGBB7421
BGBB6527

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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].
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