627-26-9

Usage

Uses

Used in Chemical Synthesis:
(2E)-2-Butenenitrile is used as a monomer for the production of synthetic rubber, contributing to the development of materials with specific properties tailored for various applications.
Used in Pharmaceutical Industry:
(2E)-2-Butenenitrile is used as a precursor in the synthesis of pharmaceuticals, playing a crucial role in the creation of new drugs and medicinal compounds.
Used in Agrochemical Production:
(2E)-2-Butenenitrile is utilized in the manufacture of agrochemicals, aiding in the development of products designed to enhance agricultural productivity and protect crops.
Used in Organic Reactions:
(2E)-2-Butenenitrile serves as a solvent in organic reactions, facilitating specific chemical processes and contributing to the synthesis of a range of organic compounds.
It is important to handle (2E)-2-Butenenitrile with care, as it is toxic and can cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken to mitigate any potential risks associated with its use.

Upstream product

• 628-20-6 4-Chlorobutyronitrile 
• 4476-02-2 2-hydroxybutanenitrile 
• 33546-80-4 3-ethoxy-butyronitrile 
• 590-18-1 (Z)-2-Butene 
• 460-19-5 ethanedinitrile 
• 23350-58-5 crotonamide 
• 603-35-0 triphenylphosphine 
• 109-75-1 but-3-enenitrile 
• 110-86-1 pyridine 
• 75-07-0 acetaldehyde 
• 372-09-8 cyanoacetic acid 
• 109-74-0 propyl cyanide 
• 4368-06-3 3-hydroxybutanenitrile 
• 67-66-3 chloroform 

Downstream Products

• 99855-23-9 3-tosylbutanenitrile 
• 118832-04-5 trans-3-(4'-tert-butylcyclohexyl)butyronitrile 
• 118799-67-0 cis-3-(4'-tert-butylcyclohexyl)butyronitrile 
• 98512-54-0 2-benzoyl-3-(4-quinazolinyl)butyronitrile 
• 103585-29-1 4-(4-morpholino-3-nitrophenyl)-4-cyano-4-morpholino-3-methyl-butyronitrile 
• 1190-76-7 (Z)-2-butenenitrile 
• 72887-16-2 5-Methoxy-3-methyl-5-phenyl-pentanenitrile 
• 73326-81-5 6-Methoxy-3-methyl-6-phenyl-hexanenitrile 
• 73326-69-9 4-((1R,2S)-2-Methoxy-cyclohexyl)-3-methyl-butyronitrile 
• 38425-90-0 3-(2-Phenylimino-cyclohexyl)-butyronitril 
• 38425-85-3 3,4-Dimethyl-5-phenyl-5-phenylimino-valeronitril 
• 185521-79-3 1-amino-3,4-dihydro-3,4-dimethyl-2-naphthalenecarbonitrile 
• 174534-15-7 1-amino-3,4-dihydro-3,7-dimethyl-2-naphthalenecarbonitrile 
• 185521-78-2 1-amino-3,4-dihydro-3-methyl-4-phenyl-2-naphthalenecarbonitrile 

Relevant academic research and scientific papers

Base controlled diverse reactivity of allyl cyanide for synthesis of multi-substituted benzenes

A base controlled regioselective 1,6-cyanoallylation of suitably functionalized 2H-pyran-2-ones has been demonstrated for the synthesis of various multi-substituted benzenes through a tandem process. We observed that lithium hydroxide provides a major product from α-attack and a minor product from γ-attack of allyl cyanide, while the use of sodium hydride as a base exclusively provides the product by γ-attack of allyl cyanide. We have also performed NMR experiments to understand the mechanistic pathway. The structure of the compound was confirmed by single crystal X-ray analysis.

LJ reaction in the preparation wittich reagent and application of glufosinate in

The present invention relates to an application of a new LJ intramolecular isomerization reaction in preparation of a wittig reagent and a herbicide of glufosinate-ammonium. With the application, a new approach of a synthesis route for preparing the wittig reagent and the glufosinate-ammonium is developed, the disadvantages of the existing wittig reaction are improved, and the industrial design of the glufosinate-ammonium production is improved.

Unusual reactivity of N-tert-butylimines under FVT conditions

Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT conditions have been studied. It has been found that at 800 °C compound 1a yielded pyrrole and crotonon

New tetraphosphorus ligands for highly linear selective hydroformylation of allyl and vinyl derivatives

New tetraphosphorus ligands have been developed and applied in the rhodium-catalyzed regioselective hydroformylation of a variety of functionalized allyl and vinyl derivatives. Remarkably high linear selectivity was obtained by these tetraphosphorus ligands. The ligand that bears strong electron-withdrawing 2,4-difluorophenyl groups is the most effective one in affording linear aldehydes. The Rh/tetraphosphorus ligand catalyst is highly effective to produce linear aldehydes from functionalized allyl derivatives with heteroatoms or aromatic groups directly adjacent to the allyl group. For vinyl derivatives, the ligand is highly linear selective for acrylic derivatives, styrene, vinyl pyridine, and vinyl phthalimide. Linear to branch ratios of 26:1 and 10:1 were obtained for the hydroformylation of styrene and allyl cyanide, respectively. New tetraphosphorus ligands have been developed and applied in the rhodium-catalyzed regioselective hydroformylation of a variety of allyl and vinyl olefins (see scheme). Remarkably high linear selectivities were obtained by these ligands. Linear-to-branch ratios of 26:1 and 10:1 were obtained for the hydroformylation of styrene and allyl cyanide, respectively. Copyright

CONTROLLED DRUG RELEASE FROM SOLID SUPPORTS

The invention relates to solid supports useful in medical applications that provide controlled release of drugs, such as peptides, nucleic acids and small molecules. The drugs are covalently coupled to the solid support through a linkage that releases the drug or a prodrug through controlled beta elimination.

CONTROLLED RELEASE FROM MACROMOLECULAR CONJUGATES

The invention relates to conjugates of macromolecular carriers and drugs comprising linkers that release the drug or a prodrug through rate-controlled beta-elimination, and methods of making and using the conjugates.

Copper-mediated synthesis of substituted 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bond formation

An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.

Direct catalytic asymmetric addition of allyl cyanide to ketones via soft lewis acid/hard bronsted base/hard lewis base catalysis

We report that a hard Lewis base substantially affects the reaction efficiency of direct catalytic asymmetric γ-addition of allyl cyanide (1a) to ketones promoted by a soft Lewis acid/hard Bronsted base catalyst. Mechanistic studies have revealed that Cu/(R,R)-Ph-BPE and Li(OC 6H4-p-OMe) serve as a soft Lewis acid and a hard Bronsted base, respectively, allowing for deprotonative activation of 1a as the rate-determining step. A ternary catalytic system comprising a soft Lewis acid/hard Bronsted base and an additional hard Lewis base, in which the basicity of the hard Bronsted base Li(OC6H4-p-OMe) was enhanced by phosphine oxide (the hard Lewis base) through a hard-hard interaction, outperformed the previously developed binary soft Lewis acid/hard Bronsted base catalytic system, leading to higher yields and enantioselectivities while using one-tenth the catalyst loading and one-fifth the amount of 1a. This second-generation catalyst allows efficient access to highly enantioenriched tertiary alcohols under nearly ideal atom-economical conditions (0.5-1 mol % catalyst loading and a substrate molar ratio of 1:2).

Looking for heteroaromatic rings and related isomers as interstellar candidates

Finding complex organic molecules in the interstellar medium (ISM) is a major concern for understanding the possible role of interstellar organic chemistry in the synthesis of prebiotic species. The present interdisciplinary report is a prospective study aimed at helping detection of heteroaromatic compounds or at least of some of their isomers in the ISM. The thermodynamic stabilities of the C4H5N, C4H4O, C4H4S families were calculated using density functional theory (DFT). It was found that pyrrole, furan and thiophene are unambiguously the most stable isomers at the 10-50 K temperatures of the ISM. Several of the less stable isomers were synthesized and flash vacuum thermolysis experiments were performed on these species. Although the detection of pyrrole in the pyrolysis of many compounds has been reported in the literature, we observed that none of its isomers led to pyrrole in these conditions, which suggests that other formation routes are to be considered. On the other hand, these three aromatic compounds present a very high stability, few % been decomposed at 1500 K by flash vacuum thermolysis; these experiments also show a great stability of crotonitrile that is the most stable compound that can be formed in these conditions. The rotational constants, dipole moments and IR frequencies of the low-lying isomers are given to encourage laboratory experiments on these prototype molecules.

Efficient conversion of aldoximes to nitriles using phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester

Aromatic aldoximes were converted to the corresponding nitriles in good to excellent yields by employing phosphoric acid diethyl ester 2- phenylbenzimidazol-1-yl ester as reagent. The method was equally effective for oximes bearing electron-donating and electron-withdrawing substituents. Graphical Abstract: [Figure not available: see fulltext.]