1,2,4,5-Tetrabromobenzene

Base Information

• Chemical Name: 1,2,4,5-Tetrabromobenzene
• CAS No.: 636-28-2
• Molecular Formula: C6H2Br4
• Molecular Weight: 393.698
• Hs Code.: 29039990
• European Community (EC) Number: 211-253-3
• NSC Number: 27002
• UNII: M25DK66LCZ
• DSSTox Substance ID: DTXSID7060910
• Nikkaji Number: J2.098B
• Wikipedia: 1,2,4,5-Tetrabromobenzene
• Wikidata: Q27283377
• Mol file: 636-28-2.mol

Synonyms:1,2,4,5-tetraBB;1,2,4,5-tetrabromobenzene

Chemical Property of 1,2,4,5-Tetrabromobenzene

Chemical Property:

• Appearance/Colour: brown crystalline needles
• Vapor Pressure: 0.000385mmHg at 25°C
• Melting Point: 180-182 °C(lit.)
• Refractive Index: 1.661
• Boiling Point: 327.5 °C at 760 mmHg
• Flash Point: 148.5 °C
• PSA: 0.00000
• Density: 2.553 g/cm³
• LogP: 4.73660
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in alcohol, benzene, and ether (Weast, 1986)
• Water Solubility.: Insoluble in water.
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 393.68490
• Heavy Atom Count: 10
• Complexity: 90.3

Purity/Quality:

99% ^*data from raw suppliers

1,2,4,5-Tetrabromobenzene ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1Br)Br)Br)Br
• Uses: 1,2,4,5-Tetrabromobenzene is a useful synthetic intermediate. It is used as a building block to prepare various aryl containing compounds such as tetrabenzanthracene, substituted pentacenes [pentacene (P237770)], n-stacking tetracene (N377650) derivatives and so on.

Technology Process of 1,2,4,5-Tetrabromobenzene

There total 36 articles about 1,2,4,5-Tetrabromobenzene 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: 87.0%

1.4-dibromobenzene (106-37-6) → 1,2,4,5-tetrabromobenzene (636-28-2)

Guidance literature:

With bromine; iron; In chloroform; at 20 - 60 ℃; for 72h;

DOI:10.1021/acs.joc.9b01317

Reference yield: 80.0%

benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 1,2,4,5-tetrabromobenzene (636-28-2)

Guidance literature:

With iron(III) chloride; bromine; In chloroform; at 0 - 45 ℃;

DOI:10.1002/chem.201100443

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

upstream raw materials:

cyclohexane

1.4-dibromobenzene

hexabromobenzene

1,5-diamino-2,4-dibromobenzene

Downstream raw materials:

1,3-diphenylbenzene

1,2,4-tribromobenzene

hexabromobenzene

2,3,5,6-tetrabromoaniline

Refernces

• 1、 Nishina, Yuta,Takami, Keishi. "Bromination of aromatic compounds using an Fe2O 3/zeolite catalyst". supporting information. p. 2380 - 2383. Retrieved 2013/02/21.
• 2、 Standera, Malte,Haefliger, Rolf,Gershoni-Poranne, Renana,Stanger, Amnon,Jeschke, Gunnar,Van Beek, Jacco D.,Bertschi, Louis,Schlueter, A. Dieter. "Evidence for fully conjugated double-stranded cycles". supporting information; experimental part. p. 12163 - 12174. Retrieved 2011/11/14.