50288-98-7

Basic information

• Product Name: 4,5-Dimethylene-cyclohex-1-ene-1,2-dicarboxylic acid dimethyl ester
• Synonyms: 4,5-Dimethylene-cyclohex-1-ene-1,2-dicarboxylic acid dimethyl ester
• CAS NO: 50288-98-7
• Molecular Weight: 222.241
• Mol File: 50288-98-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4,5-Dimethylene-cyclohex-1-ene-1,2-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dimethylene-cyclohex-1-ene-1,2-dicarboxylic acid dimethyl ester(50288-98-7)
• EPA Substance Registry System: 4,5-Dimethylene-cyclohex-1-ene-1,2-dicarboxylic acid dimethyl ester(50288-98-7)

Safety Data

• Hazardous Substances Data: 50288-98-7(Hazardous Substances Data)

Upstream product

• 50521-55-6 dimethyl 4,5-di(bromomethyl)-1,4-cyclohexadiene-1,2-dicarboxylate 
• 82167-49-5 4,5-Bis-trimethylsilanylmethyl-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester 
• 30432-16-7 1,4-dibromo-2,3-bis-bromomethyl-but-2-ene 
• 18214-55-6 2,3-bis(bromomethyl)-1,3-butadiene 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 82167-48-4 2,3-bis<(trimethyksilyl)methyl>-1,3-butadiene 
• 762-42-5 dimethyl acetylenedicarboxylate 

Downstream Products

• 82167-66-6 2-phenyl-6,7-dicarbomethoxy-3a,4,5,8,9,9a-hexahydro-1H-benzoisoindole-1,3(2H)-dione 

Relevant articles and documents

Synthesis of 3,4-disubstituted furans via unsaturated cyclic peroxides arising by photooxygenation of 2,3-bis (bromomethyl)-1,3-butadiene and derived exocyclic dienes

The reaction of 2,3-bis (bromomethyl)-1,3-butadiene (3) with singlet oxygen resulted in the formation of a peroxide (4) which rearranged with CoTPP to bis(bromomethyl)furan. Zinc-induced debromination of cycloadducts which were obtained from the [2+4] Die

Preparation and Selected Reactions of 2,3-Bis(bromomethyl)-1,3-butadiene

2,3-Bis(bromomethyl)-1,3-butadiene (1) was prepared by zinc-induced debromination of 1,4-dibromo-2,3-bis(bromomethyl)-2-butene (2).The versatility of 1 as a synthetic intermediate was demonstrated through consecutive use of its allylic bromides and conjugated diene functions, with eventual further modification of the primary reaction products.Coupling of 1 with vinylmagnesium chloride or ethynylmagnesium bromide gave highly unsaturated hydrocarbons (8-11).Reaction of 1 with nucleophiles such as sodium methoxide, sodium azide, sodium acetate, or potassium cyanide gave symmetrically disubstituted 1,3-butadienes ( 12a-d) which could in some cases be modified at the level of the substituent into other analogous dienes (12e-f).Five-membered heterocycles with exocyclic cis-fixed dienes, namely, the thiolane 13, oxolane 14, and pyrrolidines 15a-e were obtained from 1 by reaction with sodium sulfide, with potassium hydroxide, or with secondary amines, respectively.Two of the pyrrolidines (15a,c) were photolytically cyclized into the corresponding 3-azabicycloheptene derivatives (24a,b).Dimethylenehexahydropyridazine derivatives (28,29) were obtained from 1 by reaction with dimethyl azodicarboxylate and subsequent elimination of bromine.These unstable compounds could be stabilized as diene-iron tricarbonyl complexes (31-34).Carbocyclic systems were obtained from 1 by various Diels-Alder additions, such as the addition of dimethyl acetylenedicarboxylate which was followed by debromination and addition of a second molecule of the acetylenic ester to give a tetrahydronaphthalene derivative (35 -> 36 -> 37).Reaction of 1 with diiron nonacarbonyl produced three binuclear ? complexes: the known 2,2'-bis(?-allyl) complex (38) and two isomeric trimethylenemethane-type complexes (39,40) d eriving from dimerization of 1.The structure of the latter was proven by isomerization into bis(diene) complexes (41,42) and oxidation to known hydrocarbons.