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481122

Sigma-Aldrich

4-Ethynylaniline

97%

Synonym(s):
1-Amino-4-ethynylbenzene, P-APAC
Linear Formula:
HC≡CC6H4NH2
CAS Number:
Molecular Weight:
117.15
Beilstein:
2205181
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.

Packaging

5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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