CAS 20244-61-5|2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one|2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one|2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE|2,4,4,6-Tetrabromo-2,5-cyclohexadienone|2,4,4,6-四溴-2,5-...

General Information

Structure

Molecular Formula

C₆H₂Br₄O

Molecular Mass

409.69548

Exact Mass

405.68391268

Charge

InChI

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

InChIKey

NJQJGRGGIUNVAB-UHFFFAOYSA-N

Canonic Smiles

BrC1=CC(Br)(Br)C=C(C1=O)Br

Isomeric Smiles

BrC1=CC(Br)(Br)C=C(Br)C1=O

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

3.1780171

LogD (pH = 7.4)

3.1780171

Log P

3.1780171

Molar Refractivity

61.1898

Polarizability

22.900185

Polar Surface Area

17.07

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

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

IUPAC name

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

Synonyms

2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE2,4,4,6-Tetrabromo-2,5-cyclohexadienone2,4,4,6-四溴-2,5-环己二烯酮TBCO2,4,4,6-Tetrabromocyclohexa-2,5-dienone

Names and Identifiers

Registration numbers

CAS Number

PubChem SID

PubChem CID

MDL Number

EC Number

Beilstein Number

Registration numbers

Properties

Physical Property

Melting Point

ca 125°C dec.

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

05205302

MP Biomedicals Rare Chemical collection

Sigma Aldrich

302384

Packaging
5 g in glass bottle

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• For selective monobromination of imidazoles and indoles, see: J. Chem. Soc., Perkin 1, 2567 (1972).

• 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).

• 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).

• ɑ?-Unsaturated methyl ketones are brominated selectively at the methyl group: Tetrahedron, 29, 1625 (1973).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

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

IUPAC name

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

Synonyms

2,4,4,6-TETRABROMO-2,5-CYCLOHEXADIENONE2,4,4,6-Tetrabromo-2,5-cyclohexadienone2,4,4,6-四溴-2,5-环己二烯酮TBCO2,4,4,6-Tetrabromocyclohexa-2,5-dienone

Registration numbers

CAS Number

PubChem SID

PubChem CID

MDL Number

EC Number

Beilstein Number

Properties

Physical Property

Melting Point

ca 125°C dec.

Molecule Details

MP Biomedicals

05205302

MP Biomedicals Rare Chemical collection

Sigma Aldrich

302384

Packaging
5 g in glass bottle

References

PubChem Literature

From Data Sources

• For selective monobromination of imidazoles and indoles, see: J. Chem. Soc., Perkin 1, 2567 (1972).

• 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).

Bioactivity

PubChem BioAssay

Molecule

ID:107881