2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one

• ChemBase ID: 107881
• Molecular Formular: C6H2Br4O
• Molecular Mass: 409.69548
• Monoisotopic Mass: 405.68391268
• SMILES: BrC1=CC(Br)(Br)C=C(Br)C1=O
• Canonical SMILES: BrC1=CC(Br)(Br)C=C(C1=O)Br
• InChI: InChI=1S/C6H2Br4O/c7-3-1-6(9,10)2-4(8)5(3)11/h1-2H
• InChIKey: NJQJGRGGIUNVAB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one
• IUPAC Traditional name: 2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one
• Synonyms: TBCO; 2,4,4,6-Tetrabromo-2,5-cyclohexadienone; 2,4,4,6-Tetrabromocyclohexa-2,5-dienone; 2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE; 2,4,4,6-四溴-2,5-环己二烯酮

Database IDs

• CAS Number: 20244-61-5
• EC Number: 243-638-7
• MDL Number: MFCD00001589
• Beilstein Number: 2048028
• PubChem SID: 162089113; 24858249
• PubChem CID: 88433

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.1780171
• LogD (pH = 7.4): 3.1780171
• Log P: 3.1780171
• Molar Refractivity: 61.1898 cm^3
• Polarizability: 22.900185 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ca 125°C dec.

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 90%; 90+%; 95+%
• Empirical Formula (Hill Notation): C6H2Br4O

DETAILS

MP Biomedicals - 05205302

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 302384

Packaging
5 g in glass bottle

REFERENCES

• Selectively monobrominates phenols and unprotected arylamines mainly at the para position: J. Chem. Soc. (C), 3652 (1971). For tabulated results for the p-bromination of arylamines, see: Org. Synth. Coll., 6, 181 (1988).
• Reacts selectively with the terminal double bonds of polyenes: Chem. Lett., 283 (1976); Tetrahedron Lett., 26, 343 (1985). In aqueous systems, the products are the bromohydrins or, in methanol, their methyl ethers: Synthesis, 605 (1978) and references therein.
• In combination with PPh₃, can be used to convert alcohols and THP ethers to bromides with inversion of configuration: Tetrahedron Lett., 38, 1955 (1997). Silyl ethers also behave similarly: Tetrahedron Lett., 38, 7223 (1997).
• Versatile catalyst for acetalization and transacetalization of carbonyl compounds, preparation of acetonides from epoxides, and acylals from aldehydes: Bull. Chem. Soc. Jpn., 75, 2195 (2002).
• ɑ?-Unsaturated methyl ketones are brominated selectively at the methyl group: Tetrahedron, 29, 1625 (1973).
• For selective monobromination of imidazoles and indoles, see: J. Chem. Soc., Perkin 1, 2567 (1972).