3-Bromo-5-chloro-2-hydroxybenzaldehyde

Base Information

• Chemical Name: 3-Bromo-5-chloro-2-hydroxybenzaldehyde
• CAS No.: 19652-32-5
• Molecular Formula: C7H4BrClO2
• Molecular Weight: 235.465
• Hs Code.: 29130000
• European Community (EC) Number: 606-351-1
• DSSTox Substance ID: DTXSID20334112
• Nikkaji Number: J2.494.618E
• Wikidata: Q72453618
• ChEMBL ID: CHEMBL3660346
• Mol file: 19652-32-5.mol

Synonyms:3-Bromo-5-chloro-2-hydroxybenzaldehyde;19652-32-5;3-Bromo-5-chlorosalicylaldehyde;Benzaldehyde, 3-bromo-5-chloro-2-hydroxy-;MFCD00051690;3-Bromo-5-chloro-2-hydroxy-benzaldehyde;SCHEMBL264863;CHEMBL3660346;KNOYZLVIXXBBIB-UHFFFAOYSA-;DTXSID20334112;3-Bromo-5-Chloro Salicylaldehyde;BDBM111010;BBL000178;STK066944;AKOS000108220;3-Bromo-5-chlorosalicylaldehyde, 98%;AM62567;CS-W010326;DS-2336;PS-5523;3-bromo-5-chloro-2-hydroxy benzaldehyde;AC-23682;BP-20211;SY036777;B1948;BB 0245788;FT-0615172;FT-0658883;A22692;EN300-370866;J-012701;US8614253, .3-41;Z979493248

Chemical Property of 3-Bromo-5-chloro-2-hydroxybenzaldehyde

Chemical Property:

• Appearance/Colour: yellow flakes
• Vapor Pressure: 0.0185mmHg at 25°C
• Melting Point: 85-88 °C(lit.)
• Refractive Index: 1.666
• Boiling Point: 245.3 °C at 760 mmHg
• PKA: 6.20±0.23(Predicted)
• Flash Point: 102.1 °C
• PSA: 37.30000
• Density: 1.844 g/cm³
• LogP: 2.62060
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 233.90832
• Heavy Atom Count: 11
• Complexity: 153

Purity/Quality:

98% ^*data from raw suppliers

3-Bromo-5-chloro-2-hydroxybenzaldehyde ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1C=O)O)Br)Cl
• General Description: 3-Bromo-5-chlorosalicylaldehyde is a key precursor used in the synthesis of Schiff base ligands, particularly for forming N,O- or N,N,O-donor ligands in coordination chemistry. It reacts with amines like p-toluidine to yield monocondensed ligands, which subsequently form complexes with metals such as copper(II) and cadmium(II). These complexes exhibit notable antibacterial activity, with some demonstrating superior efficacy against Gram-positive bacteria like *S. aureus* compared to standard antibiotics. Additionally, the ligand-derived copper(II) complexes adopt unique coordination geometries, often stabilized by intermolecular halogen interactions (e.g., Br…Br) and metal-halogen contacts (e.g., Cu…Cl), contributing to their structural diversity and potential applications in antimicrobial research.

Technology Process of 3-Bromo-5-chloro-2-hydroxybenzaldehyde

There total 3 articles about 3-Bromo-5-chloro-2-hydroxybenzaldehyde 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: 99.0%

5-chlorosalicyclaldehyde (635-93-8) → 3-bromo-5-chlorosalicylaldehyde (19652-32-5)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃; for 72h;

Reference yield:

chloroform (67-66-3,8013-54-5) + 2-bromo-4-chlorophenol (695-96-5) → 3-bromo-5-chlorosalicylaldehyde (19652-32-5)

Guidance literature:

With sodium hydroxide; for 2h; Reflux;

DOI:10.1002/ardp.201800128

Reference yield:

→ 3-bromo-5-chlorosalicylaldehyde (19652-32-5)

Guidance literature:

upstream raw materials:

5-chlorosalicyclaldehyde

chloroform

2-bromo-4-chlorophenol

Downstream raw materials:

3-bromo-5-chloro-2-[(2-methoxyethoxy)methoxy]benzaldehyde

2-bromo-4-chloro-6-(hydroxymethyl)phenol

5-bromo-3-chloro-6-ethoxybenzaldehyde

3-bromo-5-chloro-2-hydroxybenzonitrile

Refernces

Copper(II) and cadmium(II) complexes of mono-condensed N,O- or N,N,O-Donor ligands: synthesis, crystal structures, and antibacterial activity

10.1080/24701556.2021.1917611

The research focuses on the synthesis, crystal structure, and antibacterial activity of three new complexes: two copper(II) complexes, [Cu(L1)2] (1) and [CuL2(N3)] (2), and one cadmium(II) complex, [Cd(L3)2] (3). The ligands L1, L2, and L3 are derived from 3-bromo-5-chlorosalicylaldehyde and different amines, resulting in N,O- or N,N,O-donor monocondensed Schiff bases. The synthesis involved reactions in ethanol, with the addition of NaBH4 and metal salts like Cu(ClO4)2·6H2O and Cd(CH3COO)2·2H2O. Characterization included IR, UV-Vis, and elemental analysis, with crystal structures determined by X-ray crystallography. Antibacterial assays were conducted on Gram-positive (B. subtilis, S. aureus) and Gram-negative (E. coli, P. aeruginosa) bacteria using the MTT method to determine IC50 values. The complexes showed promising antibacterial activities, with complex 1 being particularly effective against S. aureus, surpassing the activity of Penicillin G.

Crystal structure of BIS[2-((E)-(p-tolylimino) methyl)-6-bromo-4- chlorophenol]copper(II)

10.1134/S0022476612030286

The research focuses on the synthesis and crystal structure analysis of a new copper(II) complex, bis[2-((E)-(p-tolylimino)methyl)-6-bromo-4-chlorophenol]copper(II). The key chemicals involved in this research include 3-bromo-5-chloro-2-hydroxybenzaldehyde, p-toluidine, and CuCl??2H?O. These chemicals were used in the synthesis process, where the reaction of 3-bromo-5-chloro-2-hydroxybenzaldehyde with p-toluidine followed by the addition of CuCl??2H?O resulted in the formation of the complex. The synthesized complex was then characterized using single crystal X-ray diffraction analysis, revealing its crystal structure and coordination geometry. The complex crystallizes in the monoclinic system with a P21/c space group and exhibits a coordination geometry around copper(II) that is intermediate between square planar and tetrahedral. The structure is stabilized by weak intermolecular Br…Br interactions and Cu…Cl contacts, forming one-dimensional chains and two-dimensional layers.