2,5-DIBROMO-1,4-BENZENEDICARBOXALDEHYDE

Base Information

• Chemical Name: 2,5-DIBROMO-1,4-BENZENEDICARBOXALDEHYDE
• CAS No.: 63525-48-4
• Molecular Formula: C8H4Br2O2
• Molecular Weight: 291.927
• Hs Code.: 2913000090
• European Community (EC) Number: 878-593-8
• DSSTox Substance ID: DTXSID80493512
• Nikkaji Number: J1.200.134G
• Wikidata: Q72463852
• Mol file: 63525-48-4.mol

Synonyms:2,5-dibromoterephthalaldehyde;

Chemical Property of 2,5-DIBROMO-1,4-BENZENEDICARBOXALDEHYDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 189 °C
• Refractive Index: 1.685
• Boiling Point: 357.396 °C at 760 mmHg
• Flash Point: 139.818 °C
• PSA: 34.14000
• Density: 2.011 g/cm³
• LogP: 2.83660
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 291.85576
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

97% ^*data from raw suppliers

2,5-Dibromoterephthalaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1Br)C=O)Br)C=O

Technology Process of 2,5-DIBROMO-1,4-BENZENEDICARBOXALDEHYDE

There total 11 articles about 2,5-DIBROMO-1,4-BENZENEDICARBOXALDEHYDE 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: 95.0%

1,4-dibromo-2,5-bis(dibromomethyl)benzene (36711-69-0) → 2,5-dibromoterephthalaldehyde (63525-48-4)

Guidance literature:

With silver nitrate; In water; acetonitrile; for 5h; Reflux; Inert atmosphere;

DOI:10.1002/anie.201403509

Reference yield: 87.0%

→ 2,5-dibromoterephthalaldehyde (63525-48-4)

Guidance literature:

Reference yield: 70.0%

1,4-dibromo-2,5-bis(dibromomethyl)benzene (36711-69-0) + sodium methylate (124-41-4) → 2,5-dibromoterephthalaldehyde (63525-48-4) + 2,5-dibromo-4-(dibromomethyl)benzaldehyde + methyl 2,5-dibromo-4-(methoxymethyl)benzoate

Guidance literature:

1,4-dibromo-2,5-bis(dibromomethyl)benzene; sodium methylate; In methanol; toluene; for 1h; Inert atmosphere; Reflux;

With hydrogenchloride; In tetrahydrofuran; water; for 1.5h; Inert atmosphere; Reflux;

DOI:10.1021/jacs.8b06842

upstream raw materials:

1,4-dibromo-2,5-bis(dibromomethyl)benzene

1,4-dibromo-2,5-bis-diacetoxymethyl-benzene

2,5-dibromo-p-xylene

2,5-dibromoterephthalaldehyde bis(dimethyl acetal)

Downstream raw materials:

2,5-bis-(toluene-4-sulfonylamino)-terephthalaldehyde

2,5-dibromoterephthalaldehyde bis(dimethyl acetal)

2,5-Bis-tert-butylsulfanyl-benzene-1,4-dicarbaldehyde

2,5-dibromo-4-[1,3]dioxolan-2-ylbenzaldehyde

Refernces

Reversible solid-state mechanochromic luminescence originated from aggregation-induced enhanced emission-active Donor?Acceptor cruciform luminophores containing triphenylamine

10.1016/j.dyepig.2019.107689

This study investigates the design, synthesis, and properties of two torsional donor-acceptor cross-shaped luminophores, FB-CTPAEB and DFB-CTPAEB. These compounds exhibit unique intramolecular charge transfer (ICT) and solid-state fluorescence behaviors, and have high solid-state luminescence efficiencies (up to 0.693 and 0.442, respectively). 4,4''-Bis(trifluoromethyl)-[1,1':4',1''-terphenyl]-2',5'-dicarboxaldehyde (3a), prepared from 2,5-dibromoterephthalaldehyde and aromatic boronic acid 2a via Suzuki-Miyaura coupling reaction, is an intermediate for the synthesis of FB-CTPAEB. 3,3'',5,5''-Tetrakis(trifluoromethyl)-[1,1':4',1''-terphenyl]-2',5'-dicarboxaldehyde (3b), prepared from 2,5-dibromoterephthalaldehyde and aromatic boronic acid 2b via Suzuki-Miyaura coupling, is an intermediate compound used in the synthesis of DFB-CTPAEB. 2-(4-(Diphenylamino)phenyl)acetonitrile is used as the donor moiety in the Knoevenagel condensation reaction to form the final cruciform luminophore. 2,5-Dibromoterephthalaldehyde is the starting material for the synthesis of cruciform luminophores.