279-40-3

Basic information

• Product Name: 7-azabicyclo[2.2.1]heptane
• Synonyms: 7-azabicyclo[2.2.1]heptane;7-Azanorbornane;7-Azabicyclo[2.2.1]heptan...;7-azabicyclo[2.2.1]heptane(SALTDATA: HCl);7-Azabicyclo[2.2.1]heptanes
• CAS NO: 279-40-3
• Molecular Formula: C₆H₁₁N
• Molecular Weight: 97.16
• Mol File: 279-40-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 29℃ (26 Torr)
• Flash Point: 30.6°C
• Appearance: /
• Density: 0.959g/cm³
• Vapor Pressure: 5.17mmHg at 25°C
• Refractive Index: 1.486
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 11.26±0.20(Predicted)
• CAS DataBase Reference: 7-azabicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 7-azabicyclo[2.2.1]heptane(279-40-3)
• EPA Substance Registry System: 7-azabicyclo[2.2.1]heptane(279-40-3)

Safety Data

• Hazardous Substances Data: 279-40-3(Hazardous Substances Data)

Usage

General Description

7-Azabicyclo[2.2.1]heptane, also known as 7-ABC, is a bicyclic amine compound. It is a white solid with a distinct odor and is soluble in organic solvents. 7-ABC is used in the synthesis of various pharmaceuticals and agrochemicals due to its unique chemical properties and structural characteristics. It is also used as a building block in the production of heterocyclic compounds and as a chiral auxiliary in asymmetric synthesis. Additionally, 7-ABC has potential applications in the field of medicinal chemistry and drug discovery, making it a valuable compound in the chemical industry.

InChI:InChI=1/C6H11N/c1-2-6-4-3-5(1)7-6/h5-7H,1-4H2

Upstream product

• 27489-62-9 trans-4-hydroxycyclohexylamine 
• 29493-38-7 trans-4-carbobenzoxyaminocyclohexyl p-toluenesulfonate 
• 27489-63-0 trans-4-<(benzyloxycarbonyl)amino>cyclohexanol 
• 7092-27-5 7-azanorbornadiene 

Downstream Products

• 1225568-20-6 C₁₃H₁₅NO 
• 1225568-28-4 C₃₂H₃₀N₂O₃ 
• 1225568-03-5 C₁₃H₁₆N₂O₃ 
• 27514-07-4 7-azabicyclo[2.2.1]heptane hydrochloride 
• 674791-69-6 C₂₆H₃₆N₂O₃ 
• 192643-49-5 1-(7-azabicyclo[2.2.1]hept-7-yl)-2-[2-(3,5-dimethylphenyl)-3-[2-[4-(pyridin-4-yl)butylamino]ethyl]-1H-indol-5-yl)-2-methylpropan-1-one 

Relevant articles and documents

6H-THIENO`2, 3-B!PYRROLE DERIVATIVES AS ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE (GNRH)

The invention relates to a group of novel thieno-pyrrole compounds of Formula (I): wherein: R1, R2, R3, R4 and R5 are as defined in the specification, which are useful as gonadotrophin releasing hormone antagonists. The invention also relates to pharmaceutical formulations of said compounds, methods of treatment using said compounds and to processes for the preparation of said compounds.

An Evaluation of Amide Group Planarity in 7-Azabicyclo[2.2.1]heptane Amides. Low Amide Bond Rotation Barrier in Solution

Here we show that amides of bicyclic 7-azabicyclo[2.2.1]heptane are intrinsically nitrogen-pyramidal. Single-crystal X-ray diffraction structures of some relevant bicyclic amides, including the prototype N-benzoyl-7-azabicyclo[2.2.1]heptane, exhibited nitrogen-pyramidalization in the solid state. We evaluated the rotational barriers about the amide bonds of various N-benzoyl-7-azabicyclo[2.2.1]heptanes in solution. The observed reduction of the rotational barriers of the bicyclic amides, as compared with those of the monocyclic pyrrolidine amides, is consistent with a nitrogen-pyramidal structure of 7-azabicyclo[2.2.1]heptane amides in solution. A good correlation was found between the magnitudes of the rotational barrier of N-benzoyl-7-azabicyclo[2.2.1]heptanes bearing para-substituents on the benzoyl group and the Hammett's σp+ constants, and this is consistent with the similarity of the solution structures. Calculations with the density functional theory reproduced the nitrogen-pyramidal structures of these bicyclic amides as energy minima. The calculated magnitudes of electron delocalization from the nitrogen nonbonding nN orbital to the carbonyl π* orbital of the amide group evaluated by application of the bond model theory correlated well with the rotational barriers of a variety of amides, including amides of 7-azabicyclo[2.2.1]heptane. The nonplanarity of the amide nitrogen of 7-azabicyclo[2.2.1]heptanes would be derived from nitrogen-pyramidalization due to the CNC angle strain and twisting of the amide bond due to the allylic strain.