1,4-Dibromobenzene

Base Information

• Chemical Name: 1,4-Dibromobenzene
• CAS No.: 106-37-6
• Molecular Formula: C6H4Br2
• Molecular Weight: 235.906
• Hs Code.: 2903.69
• European Community (EC) Number: 203-390-2
• NSC Number: 33942
• UNII: 9991W3M5HZ
• DSSTox Substance ID: DTXSID4024012
• Nikkaji Number: J3.607B
• Wikipedia: 1,4-Dibromobenzene
• Wikidata: Q4545692
• Metabolomics Workbench ID: 55540
• ChEMBL ID: CHEMBL195407
• Mol file: 106-37-6.mol

Synonyms:1,4-dibromobenzene

Chemical Property of 1,4-Dibromobenzene

Chemical Property:

• Appearance/Colour: white or off-white powder
• Vapor Pressure: 0.134 at 35 °C (Hine et al., 1963)
• Melting Point: 86-89 °C
• Refractive Index: 1.5742
• Boiling Point: 217.9 °C at 760 mmHg
• Flash Point: 89.3 °C
• PSA: 0.00000
• Density: 1.936 g/cm³
• LogP: 3.21160
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in alcohol, benzene, chloroform, toluene and carbon tetrachloride. Insoluble in ether.
• Water Solubility.: practically insoluble
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 235.86593
• Heavy Atom Count: 8
• Complexity: 54.9

Purity/Quality:

99% ^*data from raw suppliers

1,4-Dibromobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC(=CC=C1Br)Br
• Uses: Solvent for oils; ore flotation; motor fuels; organic synthesis. 1,4-Dibromobenzene is used in the synthesis of 2,5-dibromoacetophenone, triarylamines and trans- stilbenes. It is widely used as a heavy liquid solvent as well as a motor oil additive. It finds application as an intermediate in the manufacture of organic chemicals such as dyes, pharmaceuticals and flame retardants for polymeric materials.

Technology Process of 1,4-Dibromobenzene

There total 135 articles about 1,4-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: 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

Reference yield: 11.0%

benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 1,2,4,5-tetrabromobenzene (636-28-2) + 1.4-dibromobenzene (106-37-6) + 1,2,4-tribromobenzene (615-54-3)

Guidance literature:

With oxygen; iron; 1,1-dibromomethane; at 40 ℃; for 2h; Overall yield = 520 mg;

DOI:10.1002/asia.201200322

Reference yield:

aluminium trichloride (7446-70-0) + bromobenzene (108-86-1,52753-63-6) → hydrogenchloride (7647-01-0,15364-23-5) + 1.4-dibromobenzene (106-37-6) + hydrogen bromide (10035-10-6,12258-64-9) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

upstream raw materials:

tetrachloromethane

N-Bromosuccinimide

cyclohexene

dibenzoyl peroxide

Downstream raw materials:

N-(4-bromophenyl)piperidine

1,4-bis-(trimethylsilyl)benzene

[1,1';4',1'']terphenyl

(4-bromophenyl)(diethoxy)(methyl)silane

Refernces

• 1、 Fu, Fang,Gurung, Laxman,Czaun, Miklos,Mathew, Thomas,Prakash, G.K. Surya. "ipso-Bromination/iodination of arylboronic acids: Poly(4-vinylpyridine)-Br2/I2 complexes as safe and efficient reagents". . . Retrieved 2019.
• 2、 Khan, Shabbir Afzal,Munawar, M. A.,Siddiq, M.. "Monobromination of Deactivated Active Rings Using Bromine, Mercuric Oxide, and Strong Acid". . p. 1799 - 1800. Retrieved 1988.
• 3、 Ross, Joanne C.,Clark, James H.,Macquarrie, Duncan J.,Barlow, Simon J.,Bastock, Tony W.. "The use of supported zinc bromide for the fast and selective bromination of aromatic substrates". . p. 245 - 249. Retrieved 1998.
• 4、 Ferguson et al.. "-". . p. 1250. Retrieved 1954.
• 5、 Clark, James H.,Ross, Joanne C.,Macquarrie, Duncan J.,Barlow, Simon J.,Bastock, Tony W.. "Environmentally friendly catalysis using supported reagents: The fast and selective bromination of aromatic substrates using supported zinc bromide". . p. 1203 - 1204. Retrieved 1997.
• 6、 De Almeida, Leonardo S.,De Mattos, Marcioc. S.,Esteves, Pierre M.. "Tribromoisocyanuric acid in trifluoroacetic acid: An efficient system for smooth brominating of moderately deactivated arenes". . p. 603 - 606. Retrieved 2013.
• 7、 Furuya et al.. "". . p. 997,998. Retrieved 1968.
• 8、 Kitagawa, Hideo,Shibata, Tsuyoshi,Matsuo, Jun-Ichi,Mukaiyama, Teruaki. "Efficient method for the preparation of aromatic bromides and iodides by ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate-catalyzed halogenation with bromine and iodine monochloride". . p. 339 - 345. Retrieved 2002.
• 9、 Wibaut. "". . p. 337. Retrieved 1949.
• 10、 Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi. "The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes". . p. 18040 - 18049. Retrieved 2021/05/29.