3,5-Dibromosalicylaldehyde

Base Information

• Chemical Name: 3,5-Dibromosalicylaldehyde
• CAS No.: 90-59-5
• Molecular Formula: C7H4Br2O2
• Molecular Weight: 279.916
• Hs Code.: 29130000
• European Community (EC) Number: 202-003-4
• NSC Number: 6221
• UNII: 7A260PBI3A
• DSSTox Substance ID: DTXSID1021796
• Nikkaji Number: J4.323K
• Wikidata: Q27266799
• ChEMBL ID: CHEMBL229251
• Mol file: 90-59-5.mol

Synonyms:3,5-dibromosalicylaldehyde

Chemical Property of 3,5-Dibromosalicylaldehyde

Chemical Property:

• Appearance/Colour: yellow to yellow-brown crystalline powder
• Vapor Pressure: 0.00722mmHg at 25°C
• Melting Point: 82-83.5 °C(lit.)
• Refractive Index: 1.687
• Boiling Point: 261.2 °C at 760 mmHg
• PKA: 6.08±0.23(Predicted)
• Flash Point: 111.7 °C
• PSA: 37.30000
• Density: 2.122 g/cm³
• LogP: 2.72970
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: methanol: soluble25mg/mL, clear, yellow to brown
• Water Solubility.: Soluble in methanol 25 mg/mL. Insoluble in water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 279.85576
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

98% ^*data from raw suppliers

3,5-Dibromosalicylaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1C=O)O)Br)Br
• Uses: 3,5-Dibromosalicylaldehyde reacts with alkyl cyanoacetates in the presence of ammonium acetate to yield 4H- chromenes. It can be used in the synthesis of Schiff base and can be used as reactant for synthesis of Schiff base ligands which forms mononuclear complexes with copper(II), nickel(II), zinc(II) and cobalt(II).

Technology Process of 3,5-Dibromosalicylaldehyde

There total 33 articles about 3,5-Dibromosalicylaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

salicylaldehyde (90-02-8) → 3,5-Dibromosalicylaldehyde (90-59-5)

Guidance literature:

With bromine;

DOI:10.1007/BF02494298

Reference yield: 96.0%

2-methyl-benzyl alcohol (89-95-2) → 3,5-Dibromosalicylaldehyde (90-59-5)

Guidance literature:

With sodium perborate; potassium bromide; sodium vanadate; In acetic acid; at 20 ℃; for 3h;

DOI:10.1080/00397919808004426

Reference yield: 82.0%

2,4-dibromo-6-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol (1262020-28-9) → 3,5-Dibromosalicylaldehyde (90-59-5) + 1,4-diphenyl-1,3-butadiyne (886-66-8)

Guidance literature:

With copper(II) acetate monohydrate; In N,N-dimethyl-formamide; at 110 ℃; for 5h;

DOI:10.3184/174751913X13739011239995

upstream raw materials:

ethanol

2,4-dibromo-6-dichloromethyl-phenol

2-diazidomethyl-4,6-dibromo-phenol

6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine

Downstream raw materials:

nicotinic acid-(2,4-dibromo-6-formyl-phenyl ester)

6,8-dibromocoumarin-3-carboxylic acid

N,N'-bis-(3,5-dibromo-salicylidene)-3,3'-dimethoxy-benzidine

3t-(3,5-dibromo-2-hydroxy-phenyl)-2-phenyl-acrylic acid

Refernces

2-Hydroxybenzaldehyde (2-phenylquinazolin-4-yl)hydrazones and their Zn ^II complexes: Synthesis and photophysical properties

10.1007/s11172-011-0360-z

The research focuses on the synthesis and photophysical properties of 2-hydroxybenzaldehyde (2-phenylquinazolin-4-yl)hydrazones and their ZnII complexes. The purpose of this study was to extend the synthesis of fluorine-containing quinazoline derivatives and to investigate their potential as luminescent materials, given that nitrogen heterocyclic derivatives with a phenolic OH group are known as effective ligands and many complexes based on o-hydroxy azomethines exhibit luminescent properties. The researchers synthesized a series of new quinazoline derivatives and their zinc(II) complexes, examining their structures and luminescent properties. The chemicals used in this process included 2-aminobenzonitrile, salicylaldehyde, 2-hydroxy-5-nitrobenzaldehyde, 4-hydroxysalicylaldehyde, 3,5-dibromosalicylaldehyde, and various substituted hydrazines. The study concluded that the synthesized hydrazones and their ZnII complexes exhibited interesting photophysical properties, with the complexation process leading to a bathochromic shift in the absorption spectra and blue shifts in the emission peaks. The researchers also noted that the complexation considerably lowered the Stokes shift and increased the quantum yield, suggesting that these quinazoline-containing hydrazones are promising ligand systems for the design of complexes with other metals, potentially useful in electroluminescent materials and organic light-emitting diodes (OLEDs).

A 'one-pot' phase transfer alkylation/hydrolysis of o-nitrotrifluoroacetanilides. A convenient route to N-alkyl o-phenylenediamines

10.1080/00397919608003827

The research explores a novel synthetic method for producing N-alkyl o-phenylenediamines through a one-pot phase transfer alkylation and hydrolysis process. The study aims to develop a simple and efficient route for synthesizing these compounds, which are important intermediates in the preparation of isoalloxazines (flavins) and have potential applications in various chemical and pharmaceutical fields. The key chemicals used in this research include o-nitrotrifluoroacetanilides as the starting materials, dimethylsulfate, benzyl bromide, and 1-bromopropane as electrophiles, and tetrabutylammonium chloride or benzyltriethylammonium chloride as phase transfer catalysts. The process involves a one-pot reaction where the o-nitrotrifluoroacetanilides undergo alkylation followed by hydrolysis under phase transfer conditions, yielding N-alkyl o-nitroanilines in good to excellent yields. The study concludes that this method is superior to previous methods involving o-nitroacetanilides due to the increased reactivity and ease of preparation of the trifluoroacetanilides. The findings suggest that this one-pot synthesis provides a convenient and operationally simple approach for the preparation of N-alkyl o-phenylenediamines, which can be further reduced to the desired products.