27675-38-3

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYL-1-NITROBUT-1-ENE is used as a key intermediate for the synthesis of several pharmaceuticals. Its reactivity allows it to participate in various chemical reactions, facilitating the production of different medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 3-METHYL-1-NITROBUT-1-ENE serves as an essential intermediate in the creation of various agrochemicals. Its properties make it suitable for use in developing products that can enhance crop protection and management.
Used in Rubber and Plastics Industry:
3-METHYL-1-NITROBUT-1-ENE is also utilized as an intermediate in the production of additives for the rubber and plastics industries. These additives can improve the performance characteristics of the final products, such as durability and flexibility.
Safety Precautions:
Due to its highly flammable nature and potential health hazards, including respiratory system and skin irritation, it is crucial to exercise proper handling and storage measures when working with 3-METHYL-1-NITROBUT-1-ENE. This ensures the safety of individuals and the integrity of the environment.

InChI:InChI=1/C5H9NO2/c1-5(2)3-4-6(7)8/h3-5H,1-2H3/b4-3+

Upstream product

• 141377-55-1 3-methyl-1-nitrobutan-2-ol 
• 41367-90-2 3-methyl-1-nitrobutan-2-yl acetate 
• 1809-65-0 3-methyl-1-nitrobut-2-ene 
• 75-52-5 nitromethane 
• 78-84-2 isobutyraldehyde 
• 71-43-2 benzene 

Downstream Products

• 100400-55-3 (+/-)-4r-isopropyl-1,2-dimethyl-5t-nitro-cyclohexene 
• 60899-41-4 O-methyl phenyl-α-isopropylvinylphosphinate 
• 113361-11-8 3-acetoxy-5-isopropyl-4-nitrocyclohexene 
• 142076-13-9 ((E)-2,5-Dimethyl-4-nitromethyl-hex-1-ene-1-sulfonyl)-benzene 
• 185426-03-3 (1S,2R,1'R)-(-)-N-<1-methyl-2-(2'-methyl-1'-nitromethylpropoxy)-2-phenylethyl>formamide 
• 214678-96-3 (1R,2S,1'S)-(+)-N-<1-methyl-2-(2'-methyl-1'-nitromethylpropoxy)-2-phenylethyl>formamide 

Relevant academic research and scientific papers

Effect of the α-alkyl substituent of conjugated nitroolefins on the formation of cyclic nitronic esters vs. nitrocyclopropanes in their reaction with sulfur ylides

The formation of cyclic nitronic esters (isoxazoline N-oxides) vs. nitrocyclopropanes in the reaction of conjugated nitroolefins with sulfur ylides depends on the presence of an α-alkyl substituent in the conjugated nitroolefins.

Reaction behaviour of arylamines with nitroalkenes in the presence of bismuth(iii) triflate: An easy access to 2,3-dialkylquinolines

We report the reaction behaviour of arylamines with nitroalkenes in the presence of bismuth(iii) triflate (10 mol%) and diacetoxyiodobenzene (10 mol%). We obtained 2,3-dialkylquinoline derivatives instead of the expected 3-alkylindole derivatives. The present reaction is an alternative approach for the synthesis of 2,3-dialkylquinoline derivatives under milder conditions. Furthermore, we establish the mechanistic pathway by theoretical calculations using Gaussian 09 software [B3LYP/6-311+G(d,p)], which shows that the conventional aza-Michael reaction is preferred over Michael addition. Aliphatic nitroalkenes behave in a different manner than aromatic nitroalkenes. An aza-Michael adduct gives rise to an imine by the elimination of water which may tautomerize to the corresponding enamine. The resulting imine and enamine intermediates react together to afford the desired quinoline derivatives. This protocol has the advantages of consecutive formation of one C-N and two C-C bonds, high regioselectivity, broad substrate-scope and good yields.

A Nickel-Bisdiamine Porous Organic Polymer as Heterogeneous Chiral Catalyst for Asymmetric Michael Addition to Aliphatic Nitroalkenes

We report a polystyrene-incorporated chiral nickel(II)-bisdiamine complex, which is accessible on gram-scale. This metal complex functions as a heterogeneous catalyst for the enantioselective Michael addition between malonates and aliphatic nitroalkenes,

Unprecedented Mechanism of an Organocatalytic Route to Conjugated Enynes with a Junction to Cyclic Nitronates

Conjugated enynes as well as cyclic nitronates are crucial building blocks for numerous natural products and pharmaceuticals. However, so far, no common and metal-free synthetic route to both conjugated enynes and cyclic nitronates has been reported. Herein, in situ NMR, labelling studies and theoretical calculations were combined to investigate the mechanism of the unusual triple bond formation towards conjugated enynes. Starting from nitroalkene dimers, first an isoxazolidine-2,5-diol derivative is formed as central intermediate. From this, enynes were generated by a combination of oxidation, dehydration, and retro 1,3-dipolar cycloaddition, whereas for nitronates a base induced intramolecular reorganization is proposed. While the product distribution could be controlled and high yields of nitronate were achieved, only medium to good yields for enynes were obtained due to polymerization losses. Nevertheless, we hope that these mechanistic investigations may provide a basis for further developments of organocatalytic or metal-free preparations of conjugated enynes and nitronates.

CuI-Catalysed Enantioselective Alkyl 1,4-Additions to (E)-Nitroalkenes and Cyclic Enones with Phosphino-Oxazoline Ligands

Catalytic enantioselective conjugate additions of simple alkyl groups to nitroalkenes or cyclic enones that result in the formation of tertiary C–C bonds are described. For these stereoselective addition reactions, new chiral phosphino-oxazoline ligands w

Highly Enantioselective Michael Addition of Dithiomalonates to Nitroolefins Catalyzed by New Bifunctional Chiral Thioureas

We report a highly efficient asymmetric Michael addition of dithiomalonates to trans -β-nitroole?ns catalyzed by versatile cinchona-based bifunctional thioureas, which provides the corresponding adducts in high yields (up to 92%) and with excellent enanti

Organocatalytic Enantioselective Transfer Hydrogenation of β-Amino Nitroolefins

The asymmetric organocatalytic transfer hydrogenation of β-acylamino and β-tert-butyloxycarbonylamino nitroolefins has been successfully realised in excellent enantioselectivities and yields (up to >99% ee, 97% yield) with a simple thiourea catalyst and a Hantzsch ester as hydrogen source, giving a direct access to enantiomerically pure β-amino nitroalkanes. (Figure presented.).

Straightforward synthesis of 1,2-dicyanoalkanes from nitroalkenes and silyl cyanide mediated by tetrabutylammonium fluoride

A straightforward synthesis of 1,2-dicyanoalkanes by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride is described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride is essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol is applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes, and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes.

Asymmetric palladium(II)-catalyzed cascade reaction giving quaternary amino succinimides by 1,4-addition and a nef-type reaction

Simple starting materials, high-value products: A dinuclear ferrocene-based PdII complex transforms mixtures of racemic N-benzoyl α-amino acids, nitroolefins, acetic anhydride, and manganese acetate into biologically interesting quaternary amin

Selective conversion of nitroalcohols to nitroolefins over sulfonic acid functionalized mesoporous SBA-15 material

Highly ordered 2D-hexagonal mesoporous SBA-15 has been synthesized by using triblock copolymer as template and its surface has been functionalized by 3-propylsulfonic acid group via post-synthetic grafting with 3-mercaptopropyltrimethoxy silane. A variety of α,β-substituted nitroalcohols are converted to their corresponding nitroolefins under mild reaction conditions using this 3-propylsulfonic acid-functionalized SBA-15 material. Nitroalcohols with open-chain, cyclic, and heterocyclic substituents at the α-position are smoothly converted into their corresponding nitroolefins in high yields over this solid acid catalyst. Propylsulfonic acid functionalized SBA-15 materials are found to be more efficient catalysts than microporous zeolites under similar reaction conditions.