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Usage

Uses

Used in Polymer Industry:
2-Methyleneglutaronitrile is used as a vinyl monomer for polymerization and copolymerization, contributing to the production of a variety of polymers with unique properties. Its ability to copolymerize with other monomers allows for the creation of materials with tailored characteristics, such as improved strength, flexibility, and chemical resistance.
Used in Pharmaceutical Industry:
As an intermediate, 2-Methyleneglutaronitrile plays a crucial role in the synthesis of various pharmaceutical compounds. Its reactivity and compatibility with other chemical groups make it a valuable building block for developing new drugs and therapeutic agents.
Used in Fiber Industry:
2-Methyleneglutaronitrile is also utilized as an intermediate in the production of fibers, particularly those with enhanced properties such as increased strength, durability, and resistance to environmental factors. Its incorporation into the fiber manufacturing process can lead to the development of advanced materials for various applications, including textiles, industrial fabrics, and protective gear.
Chemical Properties:
2-Methyleneglutaronitrile is a colorless liquid with specific solubility characteristics. It is slightly soluble in water, insoluble in aliphatic and alicyclic hydrocarbons, but soluble in aromatic hydrocarbons and polar organic solvents. These properties make it suitable for use in various chemical processes and reactions, contributing to its wide range of applications across different industries.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 4591, 1987 DOI: 10.1016/S0040-4039(00)96573-0

InChI:InChI=1/C6H6N2/c1-6(5-8)3-2-4-7/h1-3H2

Upstream product

• 3621-64-5 4-Hydroxyiminomithyl-pent-4-ennitril 
• 107-13-1 acrylonitrile 
• 74-90-8 hydrogen cyanide 
• 4635-87-4 3-pentenenitrile 
• 3907-06-0 3,3-Dimethylcyclopropen 
• 35691-65-7 1,2-Dibromo-2,4-dicyanobutane 

Downstream Products

• 112177-19-2 1-(3-Trifluoromethylphenyl)-2-chloro-2,4-dicyanobutane 
• 112177-13-6 1-(3,4-Dichlorophenyl)-2-chloro-2,4-dicyanobutane 
• 112177-15-8 1-(4-Carboxymethylphenyl)-2-chloro-2,4-dicyanobutane 
• 112177-10-3 1-(4-Chloro-3-nitrophenyl)-2-chloro-2,4-dicyanobutane 
• 112177-14-7 1-(2,5-Dichlorophenyl)-2-chloro-2,4-dicyanobutane 
• 35691-65-7 1,2-Dibromo-2,4-dicyanobutane 
• 4379-04-8 γ-Cyanopimelonitrile 
• 112170-55-5 3-Chloro-3-(5'-nitro-2'-trifluoromethylbenzyl)-2,6-piperidinedione 
• 112170-44-2 3-(2,6-Dichloropyridyl)-2'-trifluoromethyl-5'-nitrophenylmethane 
• 112170-54-4 3-Chloro-3-(4'-chloro-3'-nitrobenzyl)-2,6-piperidinedione 
• 112176-93-9 3-Chloro-3-(2'-methyl-4'-nitrobenzyl)-2,6-piperidinedione 
• 112176-99-5 3-Chloro-3-(3'-trifluoromethylbenzyl)-2,6-piperidinedione 
• 112170-45-3 3-(2,6-Dichloropyridyl)-2'-methyl-4'-nitrophenylmethane 
• 112176-98-4 3-Chloro-3-(4'-nitrobenzyl)-2,6-piperidinedione 

Relevant academic research and scientific papers

ELECTROCHEMISTRY AND REVERSE PULSE POLAROGRAPHIC DETERMINATION OF 1,2-DIBROMO-2,4-DICYANOBUTANE.

The electrochemical reduction of the antibacterial agent 1,2-dibromo-2,4-dicyanobutane (DBDCB, Tektamar) at mercury electrodes in actonitrile is investigated by a variety of techniques. Reverse pulse voltammetry shows that the stoichiometry of this two-electron reduction requires the liberation of two bromide ions and an organic product of composition C//6N//2H//6 per molecule of reactant. An electroanalytical method for the determination of DBDCB based on reverse pulse polarography is described and used to determine the solubility of DBDCB in water. The solubility of DBDCB in water calculated from five analyses is 0. 164% (standard deviation 0. 010%) for a 5-ms pulse time or 0. 158% (standard deviation 0. 004%) for a 50-ms pulse time.

Practical and scalable preparation of 2-methyleneglutaronitrile via an efficient and highly selective head-to-tail dimerization of acrylonitrile catalysed by low-loading of tricyclohexylphosphine

By carefully evaluating the effect of solvent, ligand, temperature, and time, the commercially available tricyclohexylphosphine was found to be a particularly effective catalyst for head-to-tail dimerization of acrylonitrile, providing an efficient, scalable, and highly selective method for preparation of the useful 2-methyleneglutaronitrile with a low catalyst loading. the Partner Organisations 2014.

Me3P-catalyzed addition of hydrogen phosphoryl compounds P(O)H to electron-deficient alkenes: 1 to 1 vs 1 to 2 adducts

Trimethyl phosphine was used as an efficient catalyst for the addition of P(O)-H compounds to electron-deficient alkenes. The addition reactions were generally conducted using a catalytic amount of Me3P under mild reaction conditions. Both 1 to 1 and 1 to 2 adducts were obtained.

Acrylonitrile dimerization preparation 2-methylene-glutaronitrile (MGN) method (by machine translation)

The invention relates to the dimerization of acrylonitrile preparation 2-methylene-glutaronitrile (MGN) method. The method uses ion liquid [Emim]BF 4 (1-methyl-3-ethyl imidazole terafluoroborate) and its analogs as reaction medium, in acrylonitrile and the ionic liquid volume ratio (the 50 [...] 1) - (the 10 [...] 1), ionic liquid and catalyst c (alkyl/aryl) diphenylphosphinobiphenyl, such as triphenylphosphine the weight ratio of (the 1 [...] 8) - (the 5 [...] 8), reaction temperature 30-70°C, reaction time 8-24h under the condition of, acrylonitrile directional dimerization synthetic MGN, can reach the reaction yield 90.7%. This method is characterized in that the reaction system is a homogeneous catalyst, the activity of the catalyst is high, the product is easy to separate, and the ionic liquid can be recycled for a plurality of times, the production cost is low. (by machine translation)

Hydrocyanation method for ethylenically unsaturated organic compounds

The invention concerns a method for hydrocyanation of ethylenically unsaturated organic compounds into compounds comprising at least a nitrile function. More particularly, it concerns a method for hydrocyanation of organic compounds comprising at least a ethylenical bond by reacting hydrogen cyanide, in the presence of a catalytic system comprising a transition metal and an organophosphorus ligand. The organophosphorus ligand is a compound with monophosphanorbornadiene structure. The invention concerns in particular hydrocyanation of butadiene into adiponitrile.

A convenient general synthesis of 3-substituted 2H-chromene derivatives

Reactions of 2-hydroxybenzaldehydes and 2-hydroxy-1-naphthaldehydes with various activated alkenes under Baylis-Hillman conditions have been shown to proceed with regioselective cyclisation to afford the corresponding 3-substituted chromene derivatives. In some cases competitive dimerisation of the alkene component was observed, and direct dimerisation in the absence of the aldehyde has been explored.

The kinetics and mechanism of the phosphorus-catalysed dimerisation of acrylonitrile

Isopropyl diarylphosphinites (Ar2POPri) catalyse the dimerisation of acrylonitrile (AN) to a mixture of cis- and trans-1,4-dicyanobut-1-ene (cis,trans-DCB-1), trans-1,4-dicyanobut-2-ene (DCB-2) and 2,4-dicyanobut-1-ene (MGN). The kinetics and mechanism of the reaction, which is a potential source of hexamethylenediamine, are reported in detail and the factors which govern rate and selectivity to DCB-1 and DCB-2 rather than MGN are elaborated.

Ruthenium-mediated selective head-to-tail dimerization of acrylic and α,β-unsaturated carbonyl compounds: Generation of an acrylate-hydride complex C5Me5Ru(PCy3)(CH2=CHCO 2Et)H

The ruthenium-hydride complex C5Me5Ru(PCy3)H3 (1a) was found to be a selective catalyst precursor for the head-to-tail dimerization of acrylic and α,β-unsaturated carbonyl compounds to produce bifunctional 1,5-dicarbonyl compounds. A new ruthenium species C5Me5Ru(PCy3)(CH2=CHCO 2Et)H (6a) was independently generated from the substitution reaction of 1a with ethyl acrylate. The exclusive formation of the head-to-tail dimers suggested that, the tertiary phosphine, generated from the substitution reaction of 6a with an olefin, was the active species for the dimerization reaction.

The kinetics and mechanism of the phosphorus-catalysed dimerisation of acrylonitrile

The kinetics and mechanism of the phosphinite-catalysed dimerisation of acrylonitrile to 1,4-dicyanobut-1-ene and 2,4-dicyanobut-1-ene are presented and discussed.

The Baylis-Hillman Reaction: A Novel Method for the Synthesis of α-Methylene-β-hydroxy Ketones and 2-Methylene-1,5-diketones

A variety of α-methylene-β-hydroxyalkanones and 2-methylene-1,5-diketones were synthesized via the BAYLIS-HILLMAN reaction, i.e., the DABCO-catalyzed coupling of methyl vinyl ketone with aldehydes and dimerization of vinylic ketones respectively.