Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

481122

Sigma-Aldrich

4-Ethynylaniline

97%

Synonym(s):

1-Amino-4-ethynylbenzene, P-APAC

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

100

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

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCS6381
MKCQ8196
MKCM0098
MKCG8788
MKCD0322

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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)
Arijit Sengupta et al.
International journal of biological macromolecules, 82, 256-263 (2015-10-18)
Amphiphilic hybrid graft copolymers were synthesized using a graft-to methodology and their protein adsorption profiles studied. Three different hydrophilic side chains were studied: hydroxypropylated high amylose starch, maltodextrin, and polyethylene glycol (PEG). In the high amylose starch compositions, there was
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service