481122

4-Ethynylaniline

97%

• Synonym(s): 1-Amino-4-ethynylbenzene, P-APAC
• Linear Formula: HC≡CC₆H₄NH₂
• CAS Number: 14235-81-5
• Molecular Weight: 117.15
• Beilstein/REAXYS Number: 2205181
• MDL number: MFCD00168824
• UNSPSC Code: 12352100
• PubChem Substance ID: 24871739
• NACRES: NA.22

Properties

• 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

Description

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.[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]

Application

4-Ethynylaniline may be used in the synthesis of N-methyliminodiethyl 4-(4-ethynylphenyliminomethyl)benzeneboronate.[4] It can also be used to prepare an acetylene ligand, HC₂-NDI (NDI= 1,4,5,8-naphthalenediimide).[5]

Used as an alkyne component in a synthesis of indoles from nitroarenes in the presence of a palladium-phenantroline catalyst.[6]

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves