706-03-6

Usage

Uses

Used in Pharmaceutical Industry:
3-(Benzylamino)propionitrile is used as a starting reagent for the synthesis of key chiral building blocks for the development of biologically active compounds. It plays a crucial role in the production of pharmaceuticals with potential therapeutic applications.
Used in Organic Chemistry:
3-(Benzylamino)propionitrile is used in the Michael addition of primary and secondary amines to acrylonitrile, which is catalyzed by lipases. This reaction is an important organic synthesis process that contributes to the development of new chemical compounds.
Used in Synthesis of Specific Compounds:
3-(Benzylamino)propionitrile is used as a starting reagent in the synthesis of several specific compounds, including:
1. (3R,4S)-1-benzyl-4-phenylpyrrolidine-3-carboxylic acid, a key chiral building block for the synthesis of biologically active compounds.
2. 1-[benzyl-(2-cyano-ethyl)-amino]-methyl-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester, a compound with potential applications in various fields.
3. 3-[benzyl-(3,5-dimethyl-pyrazol-1-ylmethyl)-amino]-propionitrile, another compound that can be used in the development of new chemical entities.

InChI:InChI=1/C10H12N2/c11-7-4-8-12-9-10-5-2-1-3-6-10/h1-3,5-6,12H,4,8-9H2/p+1

Upstream product

• 107-13-1 acrylonitrile 
• 100-46-9 benzylamine 
• 775-16-6 N-benzyl-3-pyrrolidinone 
• 25630-14-2 3-Benzylidenamino-propionitril 
• 2547-66-2 1,3,5-Tribenzyl-1,3,5-triazacyclohexane 
• 372-09-8 cyanoacetic acid 
• 151-18-8 2-cyanoethylamine 
• 100-52-7 benzaldehyde 
• 2510-33-0 N-benzyl-2-oxazolidinone 
• 1663-39-4 tert-Butyl acrylate 
• 100-51-6 benzyl alcohol 
• 2417-90-5 bromopropionitrile 
• 1074-42-6 1-benzylaziridine 
• 773837-37-9 sodium cyanide 

Downstream Products

• 100122-38-1 N-benzyl-N-dichloroacetyl-β-alanine nitrile 
• 5426-62-0 N-benzyl-β-alanine 
• 101585-36-8 N-benzyl-N-(toluene-4-sulfonyl)-β-alanine 
• 13910-48-0 N-benzyl-1,3-diaminopropane 
• 23873-65-6 3-(N-benzyl-N-methylamino)propionitrile 
• 55246-53-2 C₁₁H₁₁ClN₂O 
• 717-73-7 N-Benzyl-N-(2-cyan-aethyl)-harnstoff 
• 22100-80-7 N-Trityl-N-<β-cyan-ethyl>-benzylamin 
• 30381-16-9 N'-Benzoyl-N-benzyl-N(2-cyanaethyl)thioharnstoff 
• 30381-08-9 N'-Phenyl-N-benzyl-N(2-cyanaethyl)thioharnstoff 
• 30563-79-2 N'-Methyl-N-benzyl-N-(2-cyanethyl)-thioharnstoff 
• 67744-36-9 Ethyl-N-benzyl-2-cyanoethyl-α-aminopropionat 
• 154195-23-0 4--4-oxo-butane carboxylic acid 
• 131792-99-9 2-Bromo-N-(2-cyano-ethyl)-N-phenyl-butyramide 

Relevant academic research and scientific papers

Crystal and molecular structure of N,N,N′,N′-tetra(2- nitrilethyl) ethane-1,2-diamine and N-(2-nitrilethyl)benzylamine hydrobromide

N,N,N′,N′-tetra(2-nitrilethyl) ethane-1,2-diamine and N-(2-nitrilethyl)benzylamine hydrobromide were prepared by the addition reaction of acrylonitrile with corresponding amines, and the two structures were determined by X-ray single crystal diffraction. The two compounds crystallize in monoclinic system, and almost no classical hydrogen bond exists in the two crystal structures.

TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole

TiCl2(OTf)-SiO2 is simply prepared by immobilization of TiCl3(OTf) on silica gel surface and introduced as a non-hygroscopic Lewis acid catalyst for C-N and C-C bond formation via Michael addition reaction. A variety of structurally diverse nitrogen nucleophiles including α-aminophosphonates, aliphatic and aromatic amines and imidazole were evaluated as Michael donors. Friedel–Crafts alkylation of indoles and pyrrole was also investigated through Michael addition reaction in the presence of TiCl2(OTf)-SiO2 as a catalyst. The reactions were conducted at room temperature or 60 °C under solvent-free conditions and the desired Michael adducts were obtained in high to excellent yields.

RuO4-mediated oxidation of N-benzylated tertiary amines. Four- And three-membered azacycloalkanes as substrates

Similarly to N-benzylpiperidine and -pyrrolidine, N-benzylazetidine underwent RuO4-catalyzed oxidation by attack at both types of N-methylene C-H bonds: Endocyclic and exocyclic (benzylic). If the reaction is performed in the presence of cyanide, α-aminon

Synthesis and structure-activity relationship study of arylsulfonamides as novel potent H5N1 inhibitors

H5N1 virus, one subtype of highly pathogenic influenza A virus in human infection, has recently received attention due to its unpredictable and high mortality. In this study, a series of arylsulfonamide derivatives were identified as improved H5N1 inhibitors for the influenza treatment by systematic structure-activity relationship investigation. Among them, the most potent H5N1 inhibitor 3h exhibited excellent antiviral activity against H5N1 virus with EC50 value of 0.006 μM and selectivity index 33543.3. Moreover, the molecular docking of 3h with M2 proton channel protein provides practical way for understanding the inhibition of H5N1 with this kind of compounds.

Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts

Herein, we report the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon-heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by -COOH functionality could effectively catalyze the formation of synthetically challenging spiro/glycoquinazolinones under the present reaction conditions.

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Synthesis, Characterization and Catalytic Application of MCM 41 Supported Phenanthrolinium Dibromide Catalyst for Aza-Michael Addition Reaction in Aqueous Medium

Abstract: MCM-41 immobilized phenanthrolinium dibromide (phen-MCM-Br2) was easily prepared and applied as an efficient heterogeneous catalyst for aza-Michael addition of aromatic amines to α,β-unsaturated nitriles and nitro compounds in water. The catalyst was characterized by CHN, TGA, FT-IR, SEM, EDAX, XRD, BET, and TEM. It could be simply recovered and reused several times without significant loss of catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]

The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solventfree conditions

Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.

The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solvent-free conditions

Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.

Chemoselective catalytic conjugate addition of alcohols over amines

A highly chemoselective conjugate addition of alcohols in the presence of amines is described. The cooperative nature of the catalyst enabled chemoselective activation of alcohols over amines, allowing the conjugate addition to soft Lewis basic α,β-unsaturated nitriles. Divergent transformation of the nitrile functionality highlights the utility of the present catalysis. The cooperative nature of a copper catalyst enabled the highly chemoselective activation of alcohols in the presence of amines and thus the conjugate addition of the hydroxy group to soft Lewis basic α,β-unsaturated nitriles. The presented method proceeds under proton-transfer conditions, reverses the innate reactivity of the OH and NH groups, and does not require protecting groups. dppe=1,2-bis(diphenylphosphino) ethane, MeSal=3-methylsalicylate. Copyright