Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

20244-61-5 - 2,4,4,6-Tetrabromo-2,5-cyclohexadienone, 90+% - L00152 - Alfa Aesar

L00152 2,4,4,6-Tetrabromo-2,5-cyclohexadienone, 90+%

CAS Number
20244-61-5
Synonyms

Size Price ($) Quantity Availability
5g 0.00
25g 0.00
Add to Cart Add to Quote Request View Item

2,4,4,6-Tetrabromo-2,5-cyclohexadienone, 90+%

MDL
MFCD00001589
EINECS
243-638-7

Chemical Properties

Formula
C6H2Br4O
Formula Weight
409.70
Melting point
ca 125° dec.
Solubility
Insoluble in water.

Applications

In combination with PPh3, can be used to convert alcohols and THP ethers to bromides with inversion of configuration. It is a versatile catalyst for acetalization and transacetalization of carbonyl compounds, preparation of acetonides from epoxides, and acylals from aldehydes. It is employed for selective monobromination of imidazoles and indoles

Notes

Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

Akiko Saito, et al. An efficient method for converting alcohols to azides with 2,4,4,6-tetrabromo-2,5-cyclohexadienone/PPh3/Zn(N3)2·2Py.Tetrahedron Lett.,1997,38,(22), 3955-3958.

Habib Firouzabadi, et al. 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO) as a Versatile, Efficient, and Chemoselective Catalyst for the Acetalization and Transacetalization of Carbonyl Compounds, the Preparation of Acetonides from Epoxides and Acylals (1,1-Diacetates) from Aldehydes.Bull. Chem. Soc. Jpn.,2002,75,(10), 2195-2205.

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).

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

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.

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

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
2048028
Harmonized Tariff Code
2914.79
TSCA
No

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware