Skip to Content
Merck

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Linear Formula:
FC6H4C≡CH
CAS Number:
766-98-3
Molecular Weight:
120.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24865238
MDL number:
MFCD00168823
Beilstein/REAXYS Number:
1099285
Assay:
99%
Form:
solid

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

InChI

1S/C8H5F/c1-2-7-3-5-8(9)6-4-7/h1,3-6H

SMILES string

Fc1ccc(cc1)C#C

InChI key

QXSWHQGIEKUBAS-UHFFFAOYSA-N

assay

99%

form

solid

Quality Level

200

bp

55-56 °C/40 mmHg (lit.)

mp

26-27 °C (lit.)

density

1.048 g/mL at 25 °C (lit.)

functional group

fluoro

storage temp.

2-8°C

Related Categories

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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

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

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCM9408
BCCL6616
BCCK9442
BCCK0079
BCCJ4623

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

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)
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)
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 ×
Novel regio-and stereoselective dimerization of terminal alkynes catalyzed by rare-earth silylamide.
Komeyama K, et al.
Synthesis, 7, 1062-1066 (2004)
Pd-catalyzed coupling reaction on the organic monolayer: Sonogashira reaction on the silicon (111) surfaces.
Qu M, et al.
Applied Surface Science, 255(5), 2608-2612 (2008)
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