39872-54-3

Usage

Chemical structure

A cyclopentadiene ring with a methoxymethyl group attached to one of its carbon atoms.

Physical state

Colorless liquid.

Molecular weight

122.16 g/mol.

Uses

Building block in the synthesis of various organic compounds and pharmaceutical products; used in the production of polymers and other specialty chemicals.

Functionality

Methoxymethyl group provides stability to the cyclopentadiene ring and allows for various functionalization reactions.

Versatility

Acts as a versatile intermediate in organic synthesis.

Safety precautions

Handle with caution due to potential health and safety risks.

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 107-30-2 chloromethyl methyl ether 
• 34822-90-7 cyclopentadienylthallium 

Downstream Products

• 93405-10-8 3-(4-chloro-phenyl)-7-methoxymethyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-ene 
• 62912-32-7 7-Metoxymethylnorbornen-5-on 
• 61855-77-4 1-methoxymethylnorborn-5-en-2-one 

Relevant academic research and scientific papers

CYCLIC UNSATURATED COMPOUNDS. LXXII. ALKOXYCYCLOPENTADIENES

A convenient method was developed for the synthesis of alkoxycyclopentadienes from the relatively easily obtainable 3-hydroxytricyclo2,6>deca-4,8-diene.It was shown that the obtained substances are equilibrium mixtures of isomers with respect to the position of the system of intracyclic double bonds and contain 1- and 2-substituted cyclopentadienes in a ratio 1:2 respectively.If the alkoxy group is removed from the cyclopentadiene ring, the ratio of the isomers (1:1.5) approximates to that for alkylcyclopentadienes.

Nitroethylene: A Stable, Clean, and Reactive Agent for Organic Synthesis

Contrary to current belief, nitroethylene is a stable reagent and holds promise as a useful and reactive synthon.Nitroethylene can be prepared in 20-25-g lots, and standard, refrigerated solutions in common solvents provide a good and ready source of the reagent.The reagent purity can be easily monitored by titration against tetraphenylcyclopentadienone (tetracyclone) coupled with the isolation of the colorless crystalline adduct.With reactive substrates, nitroethylene reacts with greatest ease at low temperatures, leading to functionalized systems having potential for further elaboration.With systems that require heating, the limited stability of nitroethylene itself complicates the course of the reaction.Cyclopentadiene, 5-cyclopentadiene, 5-(methoxymethyl)cyclopentadiene, 5-(1,3-dithianyl)cyclopentadiene, 5-(trimethylsilyl)cyclopentadiene, and spiroheptadiene readily gave (4 + 2) adducts with nitroethylene, each possessing attraction as a synthetic intermediate.Adducts from furan and acetoxyfulvene undergo rearrangement via ? cleavage.The (4 + 2) adduct from 9-diazofluorene spontaneously extrudes nitrogen, leading to spironitrocyclopropane.Indole readily undergoes Michael addition to give 80percent 3-(nitroethyl)indole and 15percent of novel bis adduct.The 2,6 Michael adduct arises with 1-morpholinocyclohexene, and β-pinene undegoes an ene reaction with nitroethylene.Novel 2-nitroethyl phosphonates, useful in Wittig-Horner reactions, arise from nitroethylene and phosphites in tert-butyl alcohol.