ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Hydrocarbon halides 1-ETHYNYL-2-FLUOROBENZENE

1-ETHYNYL-2-FLUOROBENZENE

Product Name1-ETHYNYL-2-FLUOROBENZENE
CAS766-49-4
MFC8H5F
MW120.12
EINECS
MOL File766-49-4.mol

Chemical Properties

Boiling point	150 °C (lit.)
Density	1.06 g/mL at 25 °C (lit.)
refractive index	1.524-1.527
Flash point	37 °C
storage temp.	2-8°C
form	Liquid
color	Clear yellow to brownish
InChI	1S/C8H5F/c1-2-7-5-3-4-6-8(7)9/h1,3-6H
InChIKey	YFPQIXUNBPQKQR-UHFFFAOYSA-N
SMILES	Fc1ccccc1C#C
CAS DataBase Reference	766-49-4(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38-10
Safety Statements	37/39-26-16-36
RIDADR	UN 1993 3/PG 3
WGK Germany	3
Hazard Note	Irritant
HazardClass	3
PackingGroup	III
HS Code	29039990
Storage Class	3 - Flammable liquids
Hazard Classifications	Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English

Usage And Synthesis

Chemical Properties

clear yellow to brownish liquid

Uses

Employed in studies on the polymerization1 and cross-coupling2 of phenylacetylenes.

Uses

1-Ethynyl-2-fluorobenzene has been employed in the cross-coupling of phenylacetylenes. It may be used in the preparation of 3-(2-deoxy-β-D-ribofuranosyl)-6-(2-fluorophenyl)-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one and 4-(2-fluorophenylethynyl)-3-methyl-5-phenylisoxazole.

Application

General Description

1-Ethynyl-2-fluorobenzene, a fluorinated benzene derivative, is a terminal alkyne.

Synthesis

401514-42-9

766-49-4

GENERAL STEPS: 1-(2,2-dibromovinyl)-2-fluorobenzene (1.0 eq.), Cs2CO3 (2.5 eq.) and DMSO (0.1 M) were mixed in a sealed tube and heated at 115 °C overnight according to a modified literature method [10]. Upon completion of the reaction, the reaction mixture was poured into brine (20 mL/mmol) to quench the reaction. Subsequently, the mixture was extracted with tert-butyl methyl ether (3 x 10 mL/mmol) and the combined organic layers were washed with brine (15 mL/mmol) and dried with Na2SO4. Finally, all volatiles were removed to give the crude product, which was purified by fast column chromatography to give the target product 1-ethynyl-2-fluorobenzene (S3).

References

[1] Tetrahedron, 2017, vol. 73, # 33, p. 5023 - 5028

Preparation Products And Raw materials

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