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Sigma-Aldrich

4-Ethinylanilin

97%

Synonym(e):

1-Amino-4-ethinyl-benzol

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157,00 €

157,00 €

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157,00 €

About This Item

Lineare Formel:
HC≡CC6H4NH2
CAS-Nummer:
14235-81-5
Molekulargewicht:
117.15
Beilstein:
2205181
MDL-Nummer:
MFCD00168824
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24871739
NACRES:
NA.22

157,00 €

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Qualitätsniveau

100

Assay

97%

Eignung der Reaktion

reaction type: click chemistry

mp (Schmelzpunkt)

98-102 °C (dec.) (lit.)

SMILES String

Nc1ccc(cc1)C#C

InChI

1S/C8H7N/c1-2-7-3-5-8(9)6-4-7/h1,3-6H,9H2

InChIKey

JXYITCJMBRETQX-UHFFFAOYSA-N

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Allgemeine Beschreibung

4-Ethynylaniline, also known as p-ethynylaniline, is a terminal alkyne. Its synthesis using 2-methyl-3-butyn-2-ol (MEBYNOL) has been reported.[1] The transition metal catalyzed polymerization of 4-ethynylaniline to afford poly(4-ethynylaniline) has been reported.[2] The impact of the surface functionalization with 4-ethynylaniline on the thermal behavior of multi-walled carbon nanotubes (MWNTs) and graphene has been investigated.[3]

Anwendung

Used as an alkyne component in a synthesis of indoles from nitroarenes in the presence of a palladium-phenantroline catalyst.[4]
4-Ethynylaniline may be used in the synthesis of N-methyliminodiethyl 4-(4-ethynylphenyliminomethyl)benzeneboronate.[5] It can also be used to prepare an acetylene ligand, HC2-NDI (NDI= 1,4,5,8-naphthalenediimide).[6]

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

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Analysenzertifikate (COA)

Lot/Batch Number
MKCS6381
MKCQ8196
MKCM0098
MKCG8788
MKCD0322

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Die Dokumentenbibliothek aufrufen

A simple and economical synthetic route to p-ethynylaniline and ethynyl-terminated substrates.
Melissaris AP and Litt MH.
The Journal of Organic Chemistry, 59(19), 5818-5821 (1994)
Synthesis and Electro-Optical Properties of Poly(4-ethynylaniline).
Gui TL, et al.
Mol. Cryst. Liq. Cryst., 459(1), 19-299 (2006)
Platinum (II) phosphine complexes with acetylene ligands containing 1,4,5,8-naphthalenediimide: Synthesis, crystal structure and electrochemistry.
Shavaleev NM, et al.
Journal of Organometallic Chemistry, 692(4), 921-925 (2007)
Fabio Ragaini et al.
The Journal of organic chemistry, 71(10), 3748-3753 (2006-05-06)
Palladium-phenanthroline complexes efficiently catalyze the reaction of nitroarenes with arylalkynes and CO to give 3-arylindoles by an ortho-C-H functionalization of the nitroarene ring. Both electron-withdrawing and electron-donating substituents are tolerated on the nitroarene, except for bromide and activated chloride. Nitroarenes
Comparative study of the covalent diazotization of graphene and carbon nanotubes using thermogravimetric and spectroscopic techniques.
Castelain M, et al.
Physical Chemistry Chemical Physics, 15(39), 16806-16811 (2013)
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 Antwort

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

    1 Antwort

    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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