822-98-0

Usage

Uses

Used in Pharmaceutical Industry:
Bicyclo[2.2.1]heptan-2-amine is used as a building block for the synthesis of various pharmaceuticals due to its unique structural features and reactivity.
Used in Agrochemical Industry:
Bicyclo[2.2.1]heptan-2-amine is used as a precursor in the development of agrochemicals, contributing to the creation of effective and novel compounds for agricultural applications.
Used in Materials Science:
Bicyclo[2.2.1]heptan-2-amine is used as a component in the synthesis of advanced materials, leveraging its structural properties to enhance material performance in various applications.

InChI:InChI=1/C7H13N/c8-7-4-5-1-2-6(7)3-5/h5-7H,1-4,8H2

Upstream product

• 498-66-8 norborn-2-ene 
• 35718-03-7 2-Benzylaminonorbornane 
• 14370-23-1 2-Norbornyl-isothiocyanat 
• 14289-75-9 tri-norbornylborane 
• 279-23-2 norbornene 
• 72203-34-0 norbornene-2-carboxylate methyl ester 
• 1389327-48-3 N-((1R,2R,4S)-bicyclo[2.2.1]heptan-2-yl)-4-(trifluoromethyl)benzamide 
• 342029-20-3 C₇H₁₁BrZn 
• 14370-45-7 (±)-endo-2-norbornylamine hydrochloride 
• 4576-48-1 bicyclo[2.2.1]heptan-2-one oxime 
• 497-38-1 2-norbornanone 

Downstream Products

• 13908-24-2 1-Bicyclo[2.2.1]hept-2-yl-3-(2-chloro-ethyl)-urea 
• 13907-96-5 1-Bicyclo[2.2.1]hept-2-yl-3-(2-fluoro-ethyl)-urea 
• 37798-16-6 Bicyclo[2.2.1]hept-2-yl-carbamic acid 3-methylsulfanylcarbonylamino-phenyl ester 
• 17439-89-3 C₁₅H₁₉N₃O₅S 
• 37031-10-0 S-2-(2-Norbornylamino)ethanol 
• 83324-04-3 Bicyclo[2.2.1]hept-2-yl-[1-phenyl-eth-(E)-ylidene]-amine 
• 917896-43-6 N-([1R,2R,4S]-bicyclo[2.2.1]hept-2-yl)-2-methyl-5-(4-[trifluoromethyl]phenyl)-4-pyrimidinamine 
• 72810-68-5 C₁₆H₂₄N₄O₃S 
• 13909-13-2 C₁₀H₁₆ClN₃O₂ 
• 1340489-33-9 3-(exo-norbornan-2yl-aminomethyl)-phenol 
• 60-35-5 acetamide 
• 1137670-84-8 bicyclo[2.2.1]hept-2-yl-{5-[2-(2,6-dichloro-phenyl)-3H-benzoimidazol-5-yl]-[1,3,4]oxadiazol-2-yl}-amine 
• 1132922-55-4 1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid bicyclo[2.2.1]hept-2-ylamide 

Relevant academic research and scientific papers

Cobalt-Catalyzed Intermolecular Markovnikov Hydroamination of Nonactivated Olefins: N2-Selective Alkylation of Benzotriazole

Cobalt-catalyzed Markovnikov-selective hydroamination of nonactivated olefins was developed. Hydrogen atom transfer from a catalytically generated cobalt(III)-hydride complex to the olefins proceeded regioselectively, and the nucleophilic addition of benzotriazoles occurred selectively at their N2-positions. The synthetic utility of the obtained N2-alkylated benzotriazoles as stable amine protecting groups under various reaction conditions was demonstrated, and the products were also transformed into primary amines by zinc-mediated reduction.

Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents

Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C-H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C-H functionalization.

Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction

The reduction of cage ketoximes under Schwenk–Papa reaction conditions was studied to establish that the d,l, d- and l-camphor oximes are smoothly reduced to the corresponding amines in high yields. At the same time, d,l-norcamphor and adamantan-2-one oximes undergo partial catalytic deoximation to form a mixture of the corresponding amines and alcohols.

Direct Primary Amination of Alkylmetals with NH-Oxaziridine

A method for the primary electrophilic amination of primary, secondary, and tertiary organometallic substrates from a bench-stable NH-oxaziridine reagent is described. This facile and highly chemoselective transformation occurs at ambient temperature and without transition metal catalysts or purification by column chromatography to provide alkylamine products in a single step. Density functional theory (DFT) calculations revealed that, despite the basicity of alkylmetals, the direct NH-transfer pathway is favored over proton and O-transfer.

Iridium-catalyzed intermolecular hydroamination of unactivated aliphatic alkenes with amides and sulfonamides

The intermolecular addition of N-H bonds to unactivated alkenes remains a challenging, but desirable, strategy for the synthesis of N-alkylamines. We report the intermolecular amination of unactivated α-olefins and bicycloalkenes with arylamides and sulfonamides to generate synthetically useful protected amine products in high yield. Mechanistic studies on this rare catalytic reaction revealed a resting state that is the product of N-H bond oxidative addition and coordination of the amide. Rapid, reversible dissociation of the amide precedes reaction with the alkene, but an intramolecular, kinetically significant rearrangement of the species occurs before this reaction with alkene.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

ISOXAZOLES AND THEIR USE IN THE TREATMENT OF ISCHEMIC DISEASES

The present invention provides a compound of formula I, or a pharmaceutically acceptable salt thereof. These compounds are useful for the treatment of neurological, neurodegenerative, ischemic and inflammatory disorders. Accordingly, the invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of utilizing those compounds and compositions in the treatment of neurological, neurodegenerative, ischemic and inflammatory disorders.

ALKYL AND ARYL ISOTHIOCYANATES AS MASKED PRIMARY AMINES

Primary and secondary (but not tertiary) alkyl as well as aryl isothiocyanates react rapidly with 4-methyl-1,2-benzenedithiol (1) in methanol at room temperature, releasing the corresponding amines in good yields.This mild and simple procedure for unmasking amines proceeds chemospecifically with isothiocyanates even in the presence of such normally electrophilic and reactive functionalities as carboxylate ester and N-alkylphthalimide.

Reaction of organoboranes with hydrazoic acid

Organoboranes react with sodium azide in the presence of aqueous acid to yield primary amines. The reaction presumably proceeds via the anionotropic rearrangement of an organoborate complex.

Catalytic Transfer Hydrogenolysis of N-Benzyl Protecting Groups

The catalytic transfer hydrogenolysis of a number of N-benzyl compounds has been examined.Of the three hydrogen donors studied, ammonium formate and hydrazine hydrate were more effective than sodium hypophosphite.In general, debenzylation of secondary and tertiary benzylamines could be readily accomplished by refluxing the substrate with an excess of the hydrogen donor in alcoholic solvents for a few hours using catalytic amounts of 10percent palladium on carbon.The two N-benzyl heteroaromatic amines studies were stable to the above conditions.