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MilliporeSigma

404330

Sigma-Aldrich

1-Ethynyl-4-fluorobenzene

99%

Sinónimos:

(4-Fluorophenyl)acetylene, (4-Fluorophenyl)ethyne, (p-Fluorophenyl)acetylene, (p-Fluorophenyl)ethyne, 1-Fluoro-4-ethynylbenzene, 2-(4-Fluorophenyl)acetylene, 4-Ethynylfluorobenzene, 4-Fluoroethynylbenzene

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About This Item

Fórmula lineal:
FC6H4C≡CH
Número de CAS:
Peso molecular:
120.12
Beilstein/REAXYS Number:
1099285
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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.

pictograms

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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_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


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Visite la Librería de documentos

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)
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)
Novel regio-and stereoselective dimerization of terminal alkynes catalyzed by rare-earth silylamide.
Komeyama K, et al.
Synthesis, 7, 1062-1066 (2004)
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 ×

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