108561-47-3

Usage

Uses

Used in Organic Synthesis:
2,4-Cyclopentadiene-1-carbonyl chloride, 1,2,3,4,5-pentamethyl(9CI) is used as a key intermediate in organic synthesis for the production of a wide range of compounds. Its unique structure and reactivity make it a valuable component in creating complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,4-Cyclopentadiene-1-carbonyl chloride, 1,2,3,4,5-pentamethyl(9CI) serves as a crucial building block for the synthesis of various drugs. Its versatility allows for the development of new medicinal compounds with potential therapeutic applications.
Used in Agrochemical Manufacturing:
2,4-Cyclopentadiene-1-carbonyl chloride, 1,2,3,4,5-pentamethyl(9CI) is also utilized in the agrochemical sector for the synthesis of pesticides and other crop protection agents. Its incorporation into these products contributes to the development of effective and targeted solutions for agricultural challenges.
Used in Specialty Chemicals:
2,4-Cyclopentadiene-1-carbonyl chloride, 1,2,3,4,5-pentamethyl(9CI) finds application in the manufacture of specialty chemicals, where its unique properties are harnessed to create high-value products for specific industries, such as coatings, adhesives, and polymers.
Used in Chemical Research and Development:
2,4-Cyclopentadiene-1-carbonyl chloride, 1,2,3,4,5-pentamethyl(9CI) is employed as a reactant in chemical research and development, where its reactivity is explored for the discovery of new chemical reactions and processes.
Safety Precautions:
Due to its potential hazards, 2,4-Cyclopentadiene-1-carbonyl chloride, 1,2,3,4,5-pentamethyl(9CI) must be handled and stored with caution. Proper safety measures should be implemented to minimize risks associated with its reactivity.

Upstream product

• 109-99-9 tetrahydrofuran 
• 108561-45-1 Lithium-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-carboxylat 
• 73057-50-8 5-formylpentamethylcyclopentadiene 
• 4045-44-7 1,2,3,4,5-pentamethylcyclopentadiene 
• 170800-27-8 1,2,3,4,5-Pentamethyl-cyclopenta-2,4-dienecarboxylic acid 
• 75-44-5 phosgene 

Downstream Products

• 351428-89-2 1,2,3,4,5-Pentamethyl-cyclopenta-2,4-dienecarboxylic acid amide 
• 51905-34-1 pentamethylcyclopentadienyllithium 
• 4045-44-7 1,2,3,4,5-pentamethylcyclopentadiene 

Relevant academic research and scientific papers

Highly Syn-?-Facial Preference in the Diels-Alder Reactions of 1,2,3,4,5-Pentamethylcyclopentadienes Having Carboxy, Ethoxycarbonyl, and Cyano Substituents at 5-Positions

Diels-Alder reactions of 1,2,3,4,5-pentamethylcyclopentadienes having carboxy, alkoxyccarbonyl, and cyano substituents at 5-positions with N-phenylmaleimide preferentially afforded the corresponding syn-attack products with the ratio of syn/anti=80 : 20 to 100 : 0, while the diene having 5-hydroxymethyl moiety gave the anti-attack product exclusively.

Bis(pentamethylcyclopentadienyl) Ketone and Thioketone: Carbon Compounds with Preformed Diels-Alder Geometry

1,2,3,4,5-Pentamethyl-1,3-cyclopentadien-5-carbonyl chloride (2) is formed in good yields by the reaction of pentamethylcyclopentadienyllithium (1) with phosgene.The corresponding carbothioyl chloride 3 is synthesized by treatment of 1 with thiophosgene.Both acyl chlorides are stable against air and moisture and difficult to attack in SN2-type reactions.Treatment of 2 and 3 with trimethyl(pentamethylcyclopentadienyl)stannane in the presence of boron trifluoride-ether leads to bis(1,2,3,4,5-pentamethyl-1,3-cyclopentadien-5-yl) ketone (5) and thioketone (6), respectively.Even at room temperature, 5 and 6 tend to intramolecular cycloaddition reactions.X-ray crystal structure investigations of 2, 5, and 6 show the steric demand of the pentamethylcyclopentadienyl ligand and explain the untypical chemical behavior of 2 and the easy cycloaddition reactions of 5 and 6. Key Words: 1,3-Cyclopentadiene-5-carbonyl chloride, 1,2,3,4,5-pentamethyl- / 1,3-Cyclopentadiene-5-carbothioyl chloride, 1,2,3,4,5-pentamethyl- / Ketone, bis(1,2,3,4,5-pentamethyl-1,3-cyclopentadien-5-yl) / Thioketone, bis(1,2,3,4,5-pentamethyl-1,3-cyclopentadien-5-yl) / Diels-Alder preformation

On the Reaction of (Pentamethylcyclopentadienyl)lithium with Halomethanes and Formyl Compounds

In view to the synthesis of pentamethylcyclopentadienyl-substituted methane derivatives ("pentamethylcyclopentadienyl-carbon compounds") reactions of (pentamethylcyclopentadienyl)lithium with halomethans, formates, and corbon dioxide were investigated.While treatment with tri- and tetrahalomethanes leads to benzene derivatives via molecular rearrangement, reactions with formates and carbon dioxide yield pentamethylcyclopentadienyl-substituted methane derivatives.Attempts to prepare disubstituted species show the formation of by-products only.