6052-72-8

Basic information

• Product Name: 9-Azajulolidine
• Synonyms: 9-Azajulolidine;2,3,6,7-Tetrahydro-1H,5H-9-azabenzo[ij]quinolizine;4,5,6,8,9,10-Hexahydropyrido[3,2,1-ij][1,6]naphthyridine;5,6,9,10-Tetrahydro-4H,8H-pyrido-[3,2,1-ij][1,6]naphthyridine
• CAS NO: 6052-72-8
• Molecular Formula: C₁₁H₁₄N₂
• Molecular Weight: 174.24226
• Mol File: 6052-72-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 70.0 to 74.0 °C
• Boiling Point: 145°C/3mmHg(lit.)
• Flash Point: 160.7°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 7.7E-05mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 9-Azajulolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Azajulolidine(6052-72-8)
• EPA Substance Registry System: 9-Azajulolidine(6052-72-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6052-72-8(Hazardous Substances Data)

Usage

General Description

9-Azajulolidine is a heterocyclic compound with a nitrogen atom in the eight-membered ring. It is a colorless liquid with a pungent odor and is commonly used as a building block in organic synthesis. The chemical structure of 9-azajulolidine makes it a versatile intermediate for the synthesis of various pharmaceuticals, agrochemicals, and other fine chemicals. It is also used in the production of dyes, pigments, and polymers. Additionally, 9-azajulolidine has been studied for its potential applications in catalysis and as a chiral auxiliary in asymmetric synthesis. Overall, it is a valuable chemical with diverse uses in the chemical industry.

InChI:InChI=1/C11H14N2/c1-3-9-7-12-8-10-4-2-6-13(5-1)11(9)10/h7-8H,1-6H2

Upstream product

• 504-24-5 4-aminopyridine 
• 253-72-5 1,6-naphthyridine 
• 107484-80-0 ethyl 1,6-naphthyridine-8-acrylate 
• 98136-86-8 3,4-diiodo-4-aminopyridine 
• 931104-32-4 3-[4-amino-5-(3-hydroxy-prop-1-ynyl)-pyridin-3-yl]-prop-2-yn-1-ol 
• 931104-34-6 3-[4-amino-5-(3-hydroxy-propyl)-pyridin-3-yl]-propan-1-ol 
• 17965-74-1 8-bromo-1,6-naphthyridine 
• 107484-80-0 (E)-3-(1,6-naphthyridin-8-yl)acrylate ethyl ester 
• 84539-34-4 4-amino-3,5-dibromopyridine 
• 947171-59-7 C₁₃H₁₆N₂O₃ 
• 947171-58-6 C₁₅H₂₂N₂O₄ 
• 931104-36-8 3,5-bis-(3-bromo-propyl)-pyridin-4-ylamine 
• 107484-81-1 6-oxo-4,5,9,10-tetrahydro-6H,8H-pyrido<3,2,1-ij><1,6>naphthyridine 
• 93693-06-2 (+/-)-(3ar,10at,10bc)-decahydro-pyrido[3,2,1-ij][1,6]naphthyridine 

Relevant articles and documents

Modular design of pyridine-based acyl-transfer catalysts

Derivatives of 3,4-diaminopyridine have been synthesized and studied as catalysts for acyl-transfer reactions. The design of these catalysts is guided by the stability of their acetyl intermediates as determined through theoretical calculations at the B3LYP/6-311 + G(d,p)//B3LYP/6-31G(d) level of theory. The most promising catalysts have been synthesized through a three- to five-step synthesis starting from 3,4-diaminopyridine. The catalytic activity has been determined for the acylation of 1-ethynylcyclohexanol with acetic anhydride at 23°C and with isobutyric anhydride at 40°C. For both reactions, the catalytic activity depends dramatically on the substitution pattern of the diaminopyridines. Best results are obtained with catalysts containing alkyl substituents at both amine nitrogens. Georg Thieme Verlag Stuttgart.

Facile synthesis of 9-azajulolidine and its application to post-Ullmann reactions

This Letter describes the efficient synthesis of 9-azajulolidine from readily available reagents and its utilization as an effective electron-rich ligand for post-Ullmann-type reactions, that is, for C(aryl)-heteroatom (N, O, S) bond formation reactions, with dramatically enhanced reaction rates.