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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+%

Codice CAS
20244-61-5
Sinonimi

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

MDL
MFCD00001589
EINECS
243-638-7

Proprietà chimiche

Formula
C6H2Br4O
Peso formula
409.70
Punto di fusione
ca 125° dec.
Solubilità
Insoluble in water.

Applicazioni

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

Note

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

Letteratura

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).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H315-H319-H335

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

Dichiarazioni precauzionali: P260-P201-P280g-P304+P340-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves. 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.

Altri riferimenti

Beilstein
2048028
Codice tariffe armonizzato
2914.79
TSCA
No

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