2,4,4,6-Tetrabromocyclohexa-2,5-dienone

Base Information

• Chemical Name: 2,4,4,6-Tetrabromocyclohexa-2,5-dienone
• CAS No.: 20244-61-5
• Molecular Formula: C6H2Br4O
• Molecular Weight: 409.697
• Hs Code.: 29147000
• European Community (EC) Number: 243-638-7
• NSC Number: 176338
• UNII: YKX5FJE3UT
• DSSTox Substance ID: DTXSID10174089
• Nikkaji Number: J209.057K
• Wikidata: Q55524806
• Mol file: 20244-61-5.mol

Synonyms:20244-61-5;2,4,4,6-Tetrabromo-2,5-cyclohexadienone;2,4,4,6-Tetrabromocyclohexa-2,5-dienone;2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one;2,5-Cyclohexadien-1-one, 2,4,4,6-tetrabromo-;2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one;TBCO;YKX5FJE3UT;EINECS 243-638-7;NSC-176338;MFCD00001589;NSC176338;UNII-YKX5FJE3UT;SCHEMBL2649;DTXSID10174089;2,4,4,6-tetrabromocyclohexadienone;BBL102948;STL556757;AKOS015834400;AM85657;FS-4220;NSC 176338;s12013;2,4,4,6-tetrabromocyclohexadiene-1-one;2,2,4,4-Tetrabromo-2,5-Cyclohexadienone;CS-0204851;FT-0609771;FT-0609772;T1235;2,4,4,6-Tetrabromcyclohexa-2,5-dien-1-on;2,4,4,6-tetrabromo-2,5-cyclohexadiene-1-one;2,4,4,6-Tetrabromo-2,5-cyclohexadienone, 90%;A879763;J-013141

Chemical Property of 2,4,4,6-Tetrabromocyclohexa-2,5-dienone

Chemical Property:

• Appearance/Colour: orange to brown fine crystalline powder
• Vapor Pressure: 1.53E-05mmHg at 25°C
• Melting Point: 120-127 °C
• Refractive Index: 1.757
• Boiling Point: 365.8 °C at 760 mmHg
• Flash Point: 136 °C
• PSA: 17.07000
• Density: 2.897 g/cm³
• LogP: 3.61280
• Storage Temp.: 0-6°C
• Water Solubility.: Insoluble in water.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 409.67982
• Heavy Atom Count: 11
• Complexity: 240

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,4,4,6-Tetrabromocyclohexa-2,5-dienone ^*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(=O)C(=CC1(Br)Br)Br)Br
• Uses: 2,4,4,6-Tetrabromo-2,5-cyclohexadienone was used as catalyst for efficient deoxygenation of sulfoxides to their corresponding sulfides with 1,3-dithiane. It was also used as reagent for conversion of alcohols to azides.

Technology Process of 2,4,4,6-Tetrabromocyclohexa-2,5-dienone

There total 33 articles about 2,4,4,6-Tetrabromocyclohexa-2,5-dienone 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: 94.0%

phenol (108-95-2,27073-41-2) → 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one (20244-61-5)

Guidance literature:

With sodium bromate; oxalic acid; sodium bromide; In water; for 8.16667h;

Reference yield: 90.0%

2,4,6-tribromophenol (118-79-6) → 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one (20244-61-5)

Guidance literature:

With bromine; acetic acid; In water; at 0 ℃; for 0.5h;

DOI:10.1021/jo061522l

Reference yield: 87.0%

4-bromo-phenol (106-41-2) → 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one (20244-61-5)

Guidance literature:

With bromine; In ethanol; acetic acid; for 1h;

DOI:10.1023/A:1012369232421

upstream raw materials:

p-cresol

2,4,6-tribromo-4-methylcyclohexa-2,5-dienone

salicylic alcohol

3,5-dibromo-4-hydroxybenzyl alcohol

Downstream raw materials:

9-Bromoanthracene

2,4,6-tri-tert-butyl-4-(2,4,6-tribromo-phenoxy)-cyclohexa-2,5-dienone

2,4,6-tribromophenol

2,6-dibromo-1,4-benzoquinone

Refernces

• 1、 Hafez, Ahmed M.,Taggi, Andrew E.,Wack, Harald,Esterbrook, Julie,Lectka, Thomas. "Reactive Ketenes through a Carbonate/Amine Shuttle Deprotonation Strategy: Catalytic, Enantioselective α-Bromination of Acid Chlorides". . p. 2049 - 2051. Retrieved 2001.
• 2、 Matveeva,Feshin,Zefirov. "Synthesis of bromoalkenes and alkylidene dibromides by reactions of carbonyl compounds with 2,4,4,6-tetrabromo-2,5-cyclohexadienone in the presence of triphenylphosphine". . p. 52 - 55. Retrieved 2001.
• 3、 Madrahimov, Sherzod,Mostafa, Adel,Yempally, Veeranna,Fadlallah, Joelle,AlQaradawi, Siham Y.. "Electronic, infrared, mass spectrometry and thermal studies on the reaction of 2-amino-6-methylpyridine with π-acceptors". . . Retrieved 2019/09/10.
• 4、 Ganguly, Nemai C.,Nayek, Subhasis,Chandra, Sumanta. "An efficient regioselective bromination protocol of activated coumarins using 2,4,4,6-tetrabromo-2,5-cyclohexadienone". supporting information. p. 1155 - 1159. Retrieved 2013/11/06.