All Photos(1)
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:
Molecular Weight:
120.12
Beilstein:
1099285
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Soumya Sarkar et al.
Journal of the American Chemical Society, 134(10), 4509-4512 (2012-02-23)
Synthesis, characterization, and catalytic alkyne polymerization results for the first trianionic pincer alkylidyne complex, [(t)BuOCO]W≡CC(CH(3))(3)(THF)(2) (6), are described. Complex 6 is a highly active catalyst for the polymerization of acetylenes and exhibits a high turnover number (4371), activity (1.05 ×
Intermolecular Gold (I)-Catalyzed Alkyne Carboalkoxylation Reactions for the Multicomponent Assembly of β-Alkoxy Ketones.
Schultz DM, et al.
Advanced Synthesis & Catalysis, 354(18), 3451-3455 (2012)
Bis (μ-iodo) bis ((-)-sparteine) dicopper (I) catalyzed Sonogashira-type reaction under palladium and phosphine-free conditions.
Priyadarshini S, et al.
Tetrahedron Letters, 52(14), 1615-1618 (2011)
Polyhalogenoheterocyclic compounds. Part 53. Sonogashira reactions of 2, 4, 6-tribromo-3, 5-difluoropyridine.
Howardb JAK.
ARKIVOC (Gainesville, FL, United States), 11, 46-55 (2007)
Luis M Martínez-Prieto et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(52), 12779-12786 (2017-06-15)
Soluble platinum nanoparticles (Pt NPs) ligated by two different long-chain N-heterocyclic carbenes (LC-IPr and LC-IMe) were synthesized and fully characterized by TEM, high-resolution TEM, wide-angle X-ray scattering (WAXS), X-ray photoelectron spectroscopy (XPS), and solution NMR. The surface chemistry of these
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