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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+%

Numéro CAS
20244-61-5
Synonymes

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

MDL
MFCD00001589
EINECS
243-638-7

Propriétés chimiques

Formule
C6H2Br4O
Poids formulaire
409.70
Point de fusion
ca 125° dec.
Solubilité
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.

Références bibliographiques

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).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335

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

Mentions de prudence: P260u-P201-P280a-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310a-P405-P501a

Obtain special instructions before use. Wear protective gloves and eye/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
2048028
Code tarifaire harmonisé
2914.79
TSCA
No

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