30221-57-9

Basic information

• Product Name: 1-Chloro-2,3,4,5,5-pentafluoro-1,3-cyclopentadiene
• Synonyms: 1-Chloro-2,3,4,5,5-pentafluoro-1,3-cyclopentadiene;Chloro-2,3,4,5,5-pentafluorocyclopentadiene
• CAS NO: 30221-57-9
• Molecular Formula: C₅ClF₅
• Molecular Weight: 190.498516
• Mol File: 30221-57-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Chloro-2,3,4,5,5-pentafluoro-1,3-cyclopentadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-2,3,4,5,5-pentafluoro-1,3-cyclopentadiene(30221-57-9)
• EPA Substance Registry System: 1-Chloro-2,3,4,5,5-pentafluoro-1,3-cyclopentadiene(30221-57-9)

Safety Data

• Hazardous Substances Data: 30221-57-9(Hazardous Substances Data)

Usage

Type of Compound

Chlorinated derivative of pentafluorocyclopentadiene

Physical State

Colorless liquid

Odor

Strong, pungent

Uses

a. Intermediate in the synthesis of other fluorinated compounds
b. Building block for various organic reactions

Applications

a. Development of pharmaceuticals
b. Development of agrochemicals
c. Development of advanced materials

Structural Significance

Unique structure and properties make it valuable in organic chemistry

Safety Precautions

Toxic and can cause irritation to skin, eyes, and respiratory system; handle with caution

Upstream product

• 29897-30-1 2,3,4,5,6-pentafluoro-6-chloro-2,4-cyclohexadienone 
• 123412-18-0 exo-3-chloropentafluorobicyclo<2.2.0>hex-5-en-2-one 

Relevant articles and documents

Synthesis and Chemistry of Highly Fluorinated Bicyclohexenone

A series of highly fluorinated bicyclo-5-hexen-2-ones (3) and their hydrates (4) have been prepared in two steps from hexafluoro Dewar benzene (1).Photolysis of exo-3H-pentafluorobicyclo-5-hexen-2-one (3d) at low pressure in the vapor phase gave 1H-pentafluorocyclopentadiene (8), but in solution the principal product was pentafluorophenol (9).Under Favorskii conditions, exo-3-bromo- and exo-3-chloropentafluorobicyclo-5-hexen-2-one (3a and 3b) ring opened stereospecifically to 2-cyclobutenecarboxylic acids 17 and 29, respectively.Treatment of these ketones with tert-butoxide under aprotic conditions effected stereospecific cleavage to tert-butyl methylenecyclobutenecarboxylates 25 and 30.The acid (27) corresponding to 25 was obtained both from bromohydrate 4a and the acid 17, again stereospecifically, by reaction with lithium diisopropylamide.Flash vacuum pyrolysis of the hydrate (4c) of of hexafluorobicyclo-5-hexen-2-one at 300 deg C gave hexafluoro-2,4-cyclohexadienone (12), which decarbonylated at higher temperatures to yield hexafluorocyclopentadiene (13).Similarly, flash vacuum pyrolysis of 3-chloropentafluorobicyclo-5-hexen-2-one (3b) at 650 deg C gave a mixture of 1- and 2-chloropentafluorocyclopentadienes.