1,2-Dibromobenzene

Base Information

• Chemical Name: 1,2-Dibromobenzene
• CAS No.: 583-53-9
• Molecular Formula: C6H4Br2
• Molecular Weight: 235.906
• Hs Code.: 2903.69
• European Community (EC) Number: 247-544-7,209-507-3
• NSC Number: 60643
• UN Number: 2711
• UNII: 52K9W7U6EH
• DSSTox Substance ID: DTXSID0022064
• Nikkaji Number: J1.633K
• Wikipedia: 1,2-Dibromobenzene
• Wikidata: Q27117050
• Metabolomics Workbench ID: 55542
• ChEMBL ID: CHEMBL1797135
• Mol file: 583-53-9.mol

Synonyms:1,2-dibromobenzene;o-dibromobenzene;ortho-dibromobenzene

Chemical Property of 1,2-Dibromobenzene

Chemical Property:

• Appearance/Colour: Clear colourless to light yellow liquid
• Vapor Pressure: 0.129mmHg at 25°C
• Melting Point: 4-6 °C(lit.)
• Refractive Index: n20/D 1.611(lit.)
• Boiling Point: 225.421 °C at 760 mmHg
• Flash Point: 95.5 °C
• PSA: 0.00000
• Density: 1.936 g/cm³
• LogP: 3.21160
• Storage Temp.: Store at
• Solubility.: 0.075g/l
• Water Solubility.: Insoluble
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 235.86593
• Heavy Atom Count: 8
• Complexity: 62.9

Purity/Quality:

99%, ^*data from raw suppliers

1,2-Dibromobenzene ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Brominated Solvents
• Canonical SMILES: C1=CC=C(C(=C1)Br)Br
• General Description: 1,2-Dibromobenzene (also known as o-dibromobenzene) is a key intermediate in organic synthesis, particularly in the palladium-catalyzed cyanation reaction to produce phthalonitriles. 1,2-Dibromobenzene serves as a versatile substrate due to its ability to undergo efficient transformations under mild conditions, yielding high product conversions (62–97%) while accommodating diverse functional groups, including both electron-donating and electron-withdrawing substituents. Its utility in catalytic methods highlights its importance as a precursor in the development of more efficient synthetic routes compared to traditional approaches like the Rosenmund–von Braun reaction.

Technology Process of 1,2-Dibromobenzene

There total 57 articles about 1,2-Dibromobenzene 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: 100.0%

2-bromobenzoic-acid (88-65-3) → 2,3-dibromobenzene (583-53-9)

Guidance literature:

With dibromoisocyanuric acid; In dichloromethane; at 20 ℃; for 24h; Reagent/catalyst; Solvent; Temperature; UV-irradiation;

Reference yield: 81.0%

3,4-dibromoaniline (615-55-4) → 2,3-dibromobenzene (583-53-9)

Guidance literature:

3,4-dibromoaniline; With hydrogenchloride; In diethyl ether; water; for 0.0833333h;

With hydrogenchloride; sodium nitrite; In water; at 0 ℃; for 0.5h;

With hypophosphorous acid; In water; at 4 - 25 ℃; for 72h;

DOI:10.1002/ejoc.201001217

Reference yield: 72.0%

bromobenzene (108-86-1,52753-63-6) → 1.4-dibromobenzene (106-37-6) + 2,3-dibromobenzene (583-53-9)

Guidance literature:

With PyHBrCl₂; iron(III) chloride; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1055/s-2002-19794

upstream raw materials:

1,2-dibromobenzene-4-sulfonic acid

1,2-Dinitrobenzene

2-bromoaniline

benzene

Downstream raw materials:

bromobenzene

4-Phenylmorpholine

benzene

(2-bromophenyl)diphenylphosphine oxide

Refernces

Synthesis of phthalonitriles using a palladium catalyst

10.1055/s-2008-1078269

The research presents an innovative and efficient method for synthesizing phthalonitriles from o-dibromobenzenes under mild conditions. The purpose of this study is to develop an alternative to the traditional Rosenmund–von Braun reaction, which often suffers from low yields and harsh reaction conditions. The researchers utilized key chemicals such as Zn(CN)?, tris(dibenzylideneacetone)dipalladium (Pd?(dba)?), and 1,1′-bis(diphenylphosphino)ferrocene (DPPF) as catalysts in dimethylacetamide (DMAC) solvent. The method demonstrated high yields (between 62% and 97%) and was effective for various o-dibromobenzenes with different substituents, including electron-donating and electron-withdrawing groups. The study concluded that this palladium-catalyzed cyanation method is a significant improvement over existing methods, offering milder conditions, higher yields, and the ability to tolerate a wide range of functional groups without the formation of unwanted byproducts.