404330

1-Ethynyl-4-fluorobenzene

99%

• Synonym(s): (4-Fluorophenyl)acetylene, (4-Fluorophenyl)ethyne, (p-Fluorophenyl)acetylene, (p-Fluorophenyl)ethyne, 1-Fluoro-4-ethynylbenzene, 2-(4-Fluorophenyl)acetylene, 4-Ethynylfluorobenzene, 4-Fluoroethynylbenzene
• Linear Formula: FC₆H₄C≡CH
• CAS Number: 766-98-3
• Molecular Weight: 120.12
• Beilstein/REAXYS Number: 1099285
• MDL number: MFCD00168823
• UNSPSC Code: 12352100
• PubChem Substance ID: 24865238
• NACRES: NA.22

Properties

• assay: 99%
• form: solid
• refractive index: n20/D 1.516 (lit.)
• bp: 55-56 °C/40 mmHg (lit.)
• mp: 26-27 °C (lit.)
• density: 1.048 g/mL at 25 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: Fc1ccc(cc1)C#C
• InChI: 1S/C8H5F/c1-2-7-3-5-8(9)6-4-7/h1,3-6H
• InChI key: QXSWHQGIEKUBAS-UHFFFAOYSA-N

Description

General description

1-Ethynyl-4-fluorobenzene (pFAB) is a fluorobenzene derivative. Trianionic pincer alkylidyne complex catalyzed polymerization of 1-ethynyl-4-fluorobenzene has been reported. The surface of the iodophenyl-terminated organic monolayers has been modified by Sonogashira coupling of the iodophenyl groups found on the surface with pFAB. Dimerization catalyzed by Y[N(TMS)₂]₃ and 4-chloroaniline gave exclusive formation of one of three possible enediynes in excellent yield.

Application

1-Ethynyl-4-fluorobenzene may be used in the synthesis of the following:

• 3-(4-Fluorophenyl)-1H-isochromen-1-one by reacting with 2-iodobenzoic acid in the presence of copper catalyst.
• 4-Bromo-3,5-difluoro-2,6-bis-(4-fluoro-phenylethynyl)-pyridine by reacting with 2,4,6-tribromo-3,5-difluoropyridine by palladium catalyzed Sonogashira reaction.
• 1-(4-Fluorophenyl)-3-methoxy-3-(4-methoxyphenyl)propan-1-one by reacting with p-anisaldehyde.
• 5-(4-Fluorophenyl)-1-(2-nitrobenzyl)-1H-1,2,3-triazole by reacting with 1-(bromomethyl)-2-nitrobenzene in the presence of sodium azide.

1-Ethynyl-4-fluorobenzene, a substituted phenylacetylene, may be used in the synthesis of aryl acetylenes, via Sonogashira type cross coupling reaction with various haloarenes in the presence of bis(μ-iodo)bis((-)-sparteine)dicopper(I) catalyst.

Safety Information

• pictograms: GHS02,GHS07
• signalword: Danger
• hcodes: H228,H315,H319,H335
• pcodes: P210 - P240 - P241 - P261 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 4.1B - Flammable solid hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 84.2 °F - closed cup
• flash_point_c: 29 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter