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Sigma-Aldrich

4-Ethynylaniline

97%

Synonym(s):

1-Amino-4-ethynylbenzene, P-APAC

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About This Item

Linear Formula:
HC≡CC6H4NH2
CAS Number:
14235-81-5
Molecular Weight:
117.15
Beilstein:
2205181
MDL number:
MFCD00168824
UNSPSC Code:
12352100
PubChem Substance ID:
24871739
NACRES:
NA.22

Assay

97%

reaction suitability

reaction type: click chemistry

mp

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

InChI key

JXYITCJMBRETQX-UHFFFAOYSA-N

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General description

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

Application

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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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)
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)
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
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)
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