31002-73-0

Basic information

• Product Name: endo-2-Norbornanamine
• Synonyms: endo-2-Aminonorbornane;endo-2-Norbornanamine;rel-(1R*,2S*,4S*)-Bicyclo[2.2.1]heptane-2-amine;(1R,3R,4S)-bicyclo[2.2.1]heptan-3-amine
• CAS NO: 31002-73-0
• Molecular Formula: C₇H₁₃N
• Molecular Weight: 111.1848
• Mol File: 31002-73-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 160°Cat760mmHg
• Flash Point: 35°C
• Appearance: /
• Density: 0.985g/cm³
• CAS DataBase Reference: endo-2-Norbornanamine(CAS DataBase Reference)
• NIST Chemistry Reference: endo-2-Norbornanamine(31002-73-0)
• EPA Substance Registry System: endo-2-Norbornanamine(31002-73-0)

Safety Data

• Hazardous Substances Data: 31002-73-0(Hazardous Substances Data)

Upstream product

• 14370-45-7 (±)-endo-2-norbornylamine hydrochloride 
• 4576-48-1 bicyclo[2.2.1]heptan-2-one oxime 
• 497-38-1 2-norbornanone 
• 81940-38-7 endo-2-norbornyl azide 
• 22526-51-8 exo-2-azidobicyclo<2.2.1>heptane 
• 4576-48-1 2-norbornanone oxime 
• 342029-20-3 C₇H₁₁BrZn 
• 1389327-48-3 N-((1R,2R,4S)-bicyclo[2.2.1]heptan-2-yl)-4-(trifluoromethyl)benzamide 
• 72203-34-0 norbornene-2-carboxylate methyl ester 
• 498-66-8 norborn-2-ene 

Downstream Products

• 1226884-40-7 N₄-((2R)-bicyclo[2.2.1]heptan-2-yl)-6-methyl-N₂-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine 
• 498-66-8 norborn-2-ene 
• 17216-10-3 1,3-bis(naphthalen-1-yloxy)propan-2-ol 

Relevant articles and documents

Regioselective Radical Alkene Amination Strategies by Using Phosphite-Mediated Deoxygenation

Nitrogen-containing compounds are an essential motif in all disciplines of chemistry and the efficient synthesis of these frameworks is a highly sought-after goal. Presented here is a summary of recent efforts conducted by our group to develop radical-mediated amination strategies for the formal synthesis of primary amines from alkenes with exclusive anti-Markovnikov regioselectivity. We have found that N-hydroxyphthalimide is an effective reagent capable of supplying both the N and H atoms for alkene hydroamination in a group transfer radical addition-type mechanism. Furthermore, allyl-oxyphthalimide derivatives are similarly capable of radical group transfers and allow for the aminoallylation of an external alkene.

Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide

An intermolecular anti-Markovnikov hydroamination of alkenes has been developed using triethyl phosphite and N-hydroxyphthalimide. The process tolerates a wide range of alkenes, including vinyl ethers, silanes, and sulfides as well as electronically unbiased terminal and internal alkenes. The resultant N-alkylphthalimides can readily be transformed to the corresponding primary amines. Mechanistic probes indicate that the process is mediated via a phosphite promoted radical deoxygenation of N-hydroxyphthalimide to access phthalimidyl radicals.

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.