25899-50-7

Usage

Safety Profile

Moderately toxic by ingestion and skin contact. A flammable liquid. When heated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C5H7N/c1-2-3-4-5-6/h3-4H,2H2,1H3/b4-3-

Upstream product

• 5699-72-9 1-Cyanobutanol 
• 2983-06-4 2-acetoxybutanenitrile 
• 74-90-8 hydrogen cyanide 
• 106-99-0 buta-1,3-diene 
• 91-22-5 quinoline 
• 22819-90-5 1-chloro-2-cyanobutane 
• 16545-78-1 (Z)-pent-2-enenitrile 
• 42332-45-6 3-chloroquinuclidine 
• 590-18-1 (Z)-2-Butene 
• 111-69-3 hexanedinitrile 
• 4553-62-2 2-methylglutaronitrile 
• 16529-56-9 2-METHYL-3-BUTENENITRILE 
• 92885-06-8 N-chloro-1,2,5,6-tetrahydropyridine 
• 13929-94-7 1-azabicyclo[2.2.2]oct-2-ene 

Downstream Products

• 110-58-7 n-Pentylamine 
• 13284-42-9 2-pentenenitrile 
• 110-59-8 pentanonitrile 
• 16529-66-1 3-Pentenenitrile 
• 16545-78-1 (Z)-pent-2-enenitrile 
• 111-69-3 hexanedinitrile 
• 4553-62-2 2-methylglutaronitrile 
• 100-40-3 4-ethenylcyclohexene 
• 3009-88-9 5-cyanopentanoic acid methyl ester 
• 15856-96-9 (Z)-pent-2-enamide 
• 17611-82-4 alpha-ethylsuccinonitrile 

Relevant academic research and scientific papers

Rational design of efficient steric catalyst for isomerization of 2-methyl-3-butenenitrile

The catalytic isomerization of 2-methyl-3-butenenitrile (2M3BN), a model reaction in the DuPont process, has been performed using NiL4 (L=tri-O-p-tolyl phosphite) as a catalyst. The lowered catalytic activity in the isomerization with coexistence of 2-pentenenitrile (2PN) and 2-methyl-2-butenenitrile (2M2BN) indicates that both 2PN and 2M2BN are the catalyst inhibitors, and the quantitative relationship between the conversion of 2M3BN and the content of 2M2BN and 2PN is provided. DFT calculation results suggest that the inhibition effect is attributed to the generation of dead-end intermediates (2PN)NiL2 and (2M2BN)NiL2, both of which take nickel atom out of the catalytic cycle in the isomerization process. To suppress the inhibition effect, new catalytic intermediates are rationally designed based on their computational %Vbur. An efficient method that adding extra ligand 1, 5-bis(diphenylphosphino)pentane (dppp5) to the NiL4 catalyst is selected experimentally. Compared to the results obtained with NiL4 as catalyst, the (dppp5)NiL2 increases the conversion of 2M3BN from 74.5 % to 93.4 % at 3 h of reaction and provides a high selectivity to 3PN (> 98 %) at optimal conditions.

Solvent effects and activation parameters in the competitive cleavage of C-CN and C-H bonds in 2-methyl-3-butenenitrile using [(dippe)NiH]2

The reaction of [(dippe)NiH]2 with 2-methyl-3-butenenitrile (2M3BN) in solvents spanning a wide range of polarities shows significant differences in the ratio of C-H and C-CN activated products. C-H cleavage is favored in polar solvents, whereas C-C cleavage is favored in nonpolar solvents. This variation is attributed to the differential solvation of the transition states, which was further supported through the use of sterically bulky solvents and weakly coordinating solvents. Variation of the temperature of reaction of [(dippe)NiH]2 with 2M3BN in decane and N,N-dimethylformamide (DMF) allowed for the calculation of Eyring activation parameters for the C-CN activation and C-H activation mechanisms. The activation parameters for the C-H activation pathway were ΔH? = 11.4 ± 5.3 kcal/mol and ΔS? = -45 ± 15 e.u., compared with ΔH? = 17.3 ± 2.6 kcal/mol and ΔS ? = -29 ± 7 e.u. for the C-CN activation pathway. These parameters indicate that C-H activation is favored enthalpically, but not entropically, over C-C activation, implying a more ordered transition state for the former.

METHOD FOR PRODUCING 3-PENTENENITRILE

The invention relates to a method for producing 3-pentenenitrile, said method being characterised by the following steps: (a) 1,3-butadiene is reacted with hydrogen cyanide on at least one catalyst to obtain a flow (1) containing 3-pentenenitrile, 2-methyl-3-butenenitrile, the at least one catalyst, and 1,3-butadiene; (b) the flow (1) is distilled in a column to obtain a top product flow (2) rich in 1,3-butadiene, and a bottom product flow (3) that is poor in 1,3-butadiene and contains 3-pentenenitrile, the at least one catalyst, and 2-methyl-3-butenenitrile; (c) the flow (3) is distilled in a column to obtain a top product flow (4) containing 1,3-butadiene, a flow (5) in a side-tap of the column, containing 3-pentenenitrile and 2-methyl-3-butenenitrile, and a bottom product flow (6) containing the at least one catalyst; and (d) the flow (5) is distilled to obtain a top product flow (7) containing 2-methyl-3-butenenitrile, and a bottom product flow (8) containing 3-pentenenitrile.

PRODUCTION OF 3-PENTENENITRILE FROM 1,3-BUTADIENE

The invention relates to a method for producing 3-pentenenitrile by means of the hydrocyanation of 1,3-butadiene, whereby 1,3-butadiene is reacted with hydrogen cyanide in the presence of at least one catalyst, and the resulting flow is purified by distillation, the bottom temperature not exceeding 140 °C during the distillation.

METHOD FOR PRODUCING LINEAR PENTENENITRILE

The invention relates to a method for producing 3-pentenenitrile, characterised by the following steps: (a) isomerisation of an educt stream containing 2-methyl-3-butenenitrile on at least one dissolved or dispersed isomerisation catalyst to form a stream (1), which contains the isomerisation catalyst(s), 2-methyl-3-butenenitrile, 3-pentenenitrile and (Z)-2-methyl-2-butenenitrile; (b) distillation of the stream (1) to obtain a stream (2) as the overhead product, which contains 2-methyl-3-butenenitrile, 3-pentenenitrile and (Z)-2-methyl-2-butenenitrile and a stream (3) as the bottom product, which contains the isomerisation catalyst(s); (c) distillation of the stream (2) to obtain a stream (4) as the overhead product, which is enriched with (Z)-2-methyl-2-butenenitrile in comparison to stream (2), (in relation to the sum of all pentenenitriles in stream (2)) and a stream (5) as the bottom product, which is enriched with 3-pentenenitrile and 2-methyl-3-butenenitrile in comparison to stream (2), (in relation to the sum of all pentenenitriles in stream (2); (d) distillation of stream (5) to obtain a stream (6) as the bottom product, which contains 3-pentenenitrile and a stream (7) as the head product, which contains 2-methyl-3-butenenitrile.

Cryptocope rearrangement of 1,3-dicyano-5-phenyl-4,4-d2-hexa-2,5-diene. Chameleonic or centauric?

The 'centauric' model for evaluation of the effect of radical- stabilizing perturbations on the Cope rearrangement conjectures independent action of substituents that make conflicting electronic demands on the two halves of the transition region. The present test of this conjecture compares 1,3-dicyano-[5-protio]-hexa-1,5-diene (1(H)) and 2-phenylhexa-1,5-diene, with 1,3-dicyano-5-phenylhexa-1,5-diene (1(Ph)). Thermochemical information required for a proper comparison includes new data of the van't Hoff type on conjugative interaction of cyano with the carbon-carbon double bond, reevaluation of the radical-stabilizing potential of the cyano group on secondary and allyl radicals, comparison with the (reevaluated) stabilizing effect of cyano in 'nodal' positions of the Cope transition region, and determination of the enthalpy and entropy of activation of the cryptoCope rearrangement of otherwise Cope-incompetent, thermodynamically more stable hexa-2,5-dienes related by prototropy to the Cope-competent hexa-1,5-dienes above. The 'chameleonic' model is concluded to be unsatisfactory, while the 'centauric' is in better, if not complete, accord with experiment.

Cyanobutylation of amines with 2-pentenitrile

A process for the production of alkylaminonitriles by reacting 2-pentenenitrile and an alkylamine in the presence of 15 to 60% by weight water.

5,6-DIHYDROPYRIDINE : SYNTHESIS AND CHARACTERIZATION

5,6-dihydropyridine 1 is synthesized either by flash vacuum thermolysis of 1-azabicyclo oct-2-ene 3 or by dehydrochlorination over solid bases of N-chloro-1,2,5,6-tetrahydropyridine 4 and characterized at low temperature by its (1)H and (13)C nmr and ir spectra.