20244-61-5

Basic information

• Product Name: 2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE
• Synonyms: 2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIEN-1-ONE;2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE;2,5-Cyclohexadien-1-one, 2,4,4,6-tetrabromo-;2,4,4,6-tetrabromocyclohexa-2,5-dienone;2,2,4,4-Tetrabromo-2,5-Cyclohexadienone;2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE, 90+%;2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one95%;2,4,4,6-TetrabroMo-2,5-cyclohexadien-1-one, 95% 5GR
• CAS NO: 20244-61-5
• Molecular Formula: C₆H₂Br₄O
• Molecular Weight: 409.7
• EINECS: 243-638-7
• Product Categories: Bromination;Halogenation;Synthetic Organic Chemistry;C3 to C6;Carbonyl Compounds;Ketones
• Mol File: 20244-61-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 120-127 °C
• Boiling Point: 365.8 °C at 760 mmHg
• Flash Point: 136 °C
• Appearance: Clear colorless/Liquid
• Density: 2.6462 (rough estimate)
• Vapor Pressure: 1.53E-05mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 0-6°C
• Water Solubility: Insoluble in water.
• BRN: 2048028
• CAS DataBase Reference: 2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE(20244-61-5)
• EPA Substance Registry System: 2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE(20244-61-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 20244-61-5(Hazardous Substances Data)

Usage

Description

2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE is an orange to brown fine crystalline powder that forms solid charge-transfer molecular complexes with 4-(aminomethyl)piperidine. Its spectroscopic characteristics have been studied, and it is known for its chemical properties and applications in various fields.

Uses

Used in Chemical Synthesis:
2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE is used as a catalyst for efficient deoxygenation of sulfoxides to their corresponding sulfides with 1,3-dithiane. This application is crucial in the synthesis of various organic compounds and pharmaceuticals, as it allows for the selective removal of oxygen atoms from sulfoxides.
Used in Organic Chemistry:
2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE is used as a reagent for the conversion of alcohols to azides. This transformation is significant in organic chemistry, as azides are versatile intermediates that can be further converted into various functional groups, such as amines, nitriles, and alkynes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE may be utilized as a key intermediate in the synthesis of drugs and drug candidates. Its ability to facilitate the conversion of alcohols to azides and the deoxygenation of sulfoxides can be particularly useful in the development of novel therapeutic agents.
Used in Research and Development:
2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE is also used in research and development settings, where its unique chemical properties and reactivity are studied to explore new synthetic pathways and applications. Its solid charge-transfer molecular complexes with 4-(aminomethyl)piperidine provide a platform for investigating the properties and potential uses of such complexes in various fields.

InChI:InChI=1/C6H2Br4O/c7-3-1-6(9,10)2-4(8)5(3)11/h1-2H

Upstream product

• 39953-10-1 2,4,6-tribromo-4-methylcyclohexa-2,5-dienone 
• 69-72-7 salicylic acid 
• 108-95-2 phenol 
• 99-96-7 4-hydroxy-benzoic acid 
• 118-79-6 2,4,6-tribromophenol 
• 7647-01-0 hydrogenchloride 
• 7782-50-5 chlorine 
• 106-44-5 p-cresol 
• 7732-18-5 water 
• 90-01-7 salicylic alcohol 
• 2316-62-3 3,5-dibromo-4-hydroxybenzyl alcohol 
• 5532-75-2 2,6-dibromo-4-bromomethyl-phenol 
• 2432-14-6 3,5-dibromo-4-hydroxytoluene 
• 636-46-4 4-hydroxyisophthalic acid 

Downstream Products

• 118-79-6 2,4,6-tribromophenol 
• 19643-45-9 2,6-dibromo-1,4-benzoquinone 
• 14400-94-3 2,3,4,6-tetrabromophenol 
• 1521-51-3 rac-3-bromocyclohexene 
• 607-99-8 2,4,6-tribromoanisole 
• 75107-36-7 methyl 8-bromo-3,7-dimethylocta-2,6-dienoate 
• 75107-35-6 methyl 6-bromo-3,7-dimethylocta-2,7-dienoate 
• 77889-80-6 methyl 6,7-dibromo-3,7-dimethyloct-2-enoate 
• 75107-37-8 6-bromo-3,7-dimethylocta-2,7-dienyl acetate 
• 75107-39-0 (E)-6,7-dibromo-3,7-dimethyloct-2-en-1-yl acetate 
• 75107-38-9 8-bromo-3,7-dimethylocta-2,7-dienyl acetate 
• 108-86-1 bromobenzene 
• 108-95-2 phenol 
• 331991-08-3 (S)-2-bromo-3-phenoxypropionic acid (2,4,6-tribromophenyl) ester 

Relevant articles and documents

Scalable methodology for the catalytic, asymmetric α-bromination of acid chlorides

The optimization of a practical, catalytic, asymmetric process for the α-bromination of acid chlorides to produce synthetically versatile, optically active α-bromoesters is reported. A range of products is produced in high enantioselectivity and moderate to good chemical yields with retention of both upon scale-up. The reactions herein are catalyzed by cinchona alkaloid derivatives, with the best performance achieved by the use of a proline cinchona alkaloid conjugate designed in a de novo fashion.

A mechanistic study on the catalytic, asymmetric α-bromination of acid chlorides

The mechanism of the catalytic, asymmetric α-bromination of acid chlorides is probed through a series of crossover experiments, ion-pairing tests, and kinetic resolution studies to shed light on the factors that contribute to, and limit the production of, optically-active α-bromo esters. In order to understand better the observed sense of induction, as well as the high degree of enantiomeric excess exhibited by these products, extensive molecular modeling is employed on the relevant transition states. Finally, the usefulness of the α-bromo ester products is demonstrated by their simple derivatization into chiral epoxides. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Electronic, infrared, mass spectrometry and thermal studies on the reaction of 2-amino-6-methylpyridine with π-acceptors

The spectrophotometric characteristics of the solid charge-transfer molecular complexes (CT) formed in the reaction of the electron donor 2-amino-6-methylpyridine (2A6MPy) with the π-acceptors tetracyanoethylene (TCNE), 2,3-dichloro-5,6-dicyano-1,4-benzoq

Studies directed toward total synthesis of rhodocomatulins: A regioselective synthesis of brominated hydroxyanthraquinones by anionic annulations

In this work, brominated hydroxyanthraquinones, which are the core structural motif of naturally occurring bromorhodocomatulins, were successfully synthesized using Hauser annulation reaction as the key step. When brominated Michael acceptors (brominated p-quinone monoketals) and cyanophthalides or bromocyanophthalides (Hauser donors) were reacted under the annulation conditions, brominated anthraquinones were obtained with 81–87% yields for four examples. On acidic quenching, products were obtained as solid which were separated by filtration and purified by recrystallization in acetone. No chromatography was required.