71058-67-8

Basic information

• Product Name: 1,6-diazabicyclo[4.4.4]tetradecane
• Synonyms: 1,6-diazabicyclo[4.4.4]tetradecane
• CAS NO: 71058-67-8
• Molecular Formula: C12H24N2
• Molecular Weight: 196.33
• Mol File: 71058-67-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 170-175 °C
• Boiling Point: 283.5°C at 760 mmHg
• Flash Point: 116.4°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 0.00315mmHg at 25°C
• Refractive Index: 1.517
• PKA: 9.90±0.20(Predicted)
• CAS DataBase Reference: 1,6-diazabicyclo[4.4.4]tetradecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-diazabicyclo[4.4.4]tetradecane(71058-67-8)
• EPA Substance Registry System: 1,6-diazabicyclo[4.4.4]tetradecane(71058-67-8)

Safety Data

• Hazardous Substances Data: 71058-67-8(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic compound

Use

Strong organic base in organic synthesis

Physical state

Colorless, high-boiling liquid

Solubility

Highly soluble in polar solvents such as water and acetone

Applications

a. Catalyst for various reactions (deprotonation, alkylation, dehydrohalogenation)
b. Activating agent for polymerization reactions
c. Pharmaceutical manufacturing
d. Production of chemical intermediates

Safety precautions

Handle with caution and use in a well-ventilated environment due to strong basic properties and high reactivity

InChI:InChI=1/C12H24N2/c1-2-8-14-11-5-3-9-13(7-1)10-4-6-12-14/h1-12H2

Relevant articles and documents

Reaction of a Stable NN Bonded Radical Cation with Free Radicals generated by Pulse Radiolysis: Exceedingly Rapid Hydrogen Abstraction from C-H Bonds

Absolute rate constants have been measured for the reaction of the NN three-electron bonded 1,6-diazabicyclododecane radical cation (+.) with various free radicals produced by means of pulse radiolysis.Reduction and oxidation reactions occur with rate constants generally somewhat below the diffusion limit.This is considered to reflect the inwardly oriented structure of the +..High rate constants (ca. 1E9 mol-1 dm3 s-1) have been measured for hydrogen-atom abstraction from +. by almost all radicals except eeq-.The most remarkable of these reactions appears to be H-atom abstraction by a thiyl radical .>, which occurs with k 3.2E9 mol-1 dm3 s-1.This indicates highly labile C-H bonds in +., which are considered to be those located on CH2 groups α to the nitrogen atoms.The fast radical-radical H-atom transfer is considered to be energetically assisted by favourable stereoelectronics and least heavy atom motion.

Reductive cleavage of Propellane-type Hydrazinium Dications as a Route to Medium-sized Ring Bicyclic Diamines with Bridgehead Nitrogen Atoms

Procedures are described for the preparation of 1,5-diazoniatricyclodecane (9), 1,5-diazoniatricycloundecane (10), 1,6-diazoniatricyclododecane (11), 1,6-diazoniatricyclotridecane (12), and 1,6-diazoniatricyclotetradecane (13) salts by the alkylation of 1,5-diazabicyclooctane and 1,6-diazabicyclodecane with suitable difunctional molecules XmY.The central N-N bond of these propellane-type hydrazinium dications may be cleaved by a variety of reducing agents to yield the bicyclic diamines 1,5-diazabicyclodecane (21), 1,5-diazabicycloundecane (22), 1,6-diazabicyclo-dodecane (23), 1,6-diazabicyclotridecane (24), and 1,6-diazabicyclotetradecane (25).The scope and limitations of this synthetic route to medium-sized ring bicyclic diamines are discussed.