14658-95-8

Basic information

• Product Name: 1,3-DIBROMOAZULENE
• Synonyms: 1,3-DIBROMOAZULENE
• CAS NO: 14658-95-8
• Molecular Formula: C₁₀H₆Br₂
• Molecular Weight: 285.96264
• Mol File: 14658-95-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 88.0 to 92.0 °C
• Boiling Point: 334.3°C at 760 mmHg
• Flash Point: 181.1°C
• Appearance: /
• Density: 1.834g/cm³
• Vapor Pressure: 0.00025mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 1,3-DIBROMOAZULENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIBROMOAZULENE(14658-95-8)
• EPA Substance Registry System: 1,3-DIBROMOAZULENE(14658-95-8)

Safety Data

• Hazardous Substances Data: 14658-95-8(Hazardous Substances Data)

Usage

Type of compound

Brominated derivative of azulene

Azulene

Bicyclic aromatic hydrocarbon

Physical state

Yellowish solid

Solubility

Soluble in organic solvents

Odor

Distinct, aromatic

Uses

Building block in synthesis of organic compounds, reagent in chemical reactions

Applications

Production of dyes and pigments, potential use in materials science and electronics

Safety

Toxic and potentially hazardous to health and environment

Handling

Careful handling required

InChI:InChI=1/C10H6Br2/c11-9-6-10(12)8-5-3-1-2-4-7(8)9/h1-6H

Upstream product

• 1206-88-8 ethyl azulene-1-carboxylate 
• 1187945-65-8 1,3-dibromo-2-iodoazulene 
• 99177-25-0 1,2,3,4,5,6-hexahydro-azulene 
• 61035-76-5 2-bromoazulene 
• 275-51-4 azulene 
• 36044-42-5 1,3-diiodoazulene 

Downstream Products

• 78049-27-1 1-phenoxyazulene 
• 275-51-4 azulene 
• 36044-42-5 1,3-diiodoazulene 
• 862421-94-1 1,3-bis(4-bromophenyl)azulene 
• 36044-41-4 2-iodoazulene 
• 1374759-27-9 1,3-bis-(5',5''-phenyl-3',3''-methylthienyl)azulene 
• 1374759-26-8 1,3-bis(3'-phenylthienyl)azulene 
• 61035-81-2 1,3-bis(phenylethynyl)azulene 

Relevant articles and documents

Synthesis and crystal structures of N,N-diarylacetamides bearing two azulene rings

N,N-Diarylacetamides bearing two azulene rings on the amide nitrogen were synthesized and their crystal structures were determined. The dihedral angle between the amide plane and the aryl ring located on the same side as the amide oxygen atom is influenced by the position of linkage of the aromatic ring to the nitrogen atom, and a 2-azulenyl group located on the same side as amide oxygen atom tends to be coplanar with the amide plane. This feature may be useful in the design of molecular devices and supramolecules.

Synthesis and structural characterization of diazulenylborinic acid

Diazulenylborinic acid 1 was synthesized by the reaction of 1,3-dibromoazulen-2-yllithium (2) with 1,3-dibromoazulen-2-ylboronic acid ethylene glycol ester (7d). The X-Ray crystallographic study of 1 revealed that it forms a dimeric structure through intermolecular hydrogen bonding between the hydroxyl groups. To obtain the tetracoordinate borinate derivative from 1, the attempted esterification of 1 with N,N-dimethylethanolamine did not give corresponding borinate 8 but resulted in the unexpected protodeboronation to give parent 1,3-dibromoazulene (4). The 13C and 11B NMR studies of 1 in the presence of Et3N revealed the change in the φ-polarization of the azulenyl group accompanied by the change in the geometry of the boron to a tetracoordinate structure.

A convenient synthesis of functionalized azulenes via negishi cross-coupling

A mild and effective method for the synthesis of functionalized azulenes is described. Negishi cross-coupling of bromoazulenes with functionalized aromatic, heterocyclic, benzylic, and alkylic organozinc reagents affords substituted azulenes in good yields. Functional groups, including ethoxycarbonyl, cyano, methoxy, fluoro, chloro, and bromo are well tolerated. Additionally, a one-pot procedure for introducing two different substituents into positions 1 and 3 of azulene through cross-coupling reaction is described for the first time.