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18742-02-4 - 2-(2-Bromoethyl)-1,3-dioxolane, 95%, stab. with silver - 3-Bromopropanal 1,2-ethanediol acetal - 3-Bromopropionaldehyde ethylene acetal - A11441 - Alfa Aesar

A11441 2-(2-Bromoethyl)-1,3-dioxolane, 95%, stab. with silver

Numéro de CAS
18742-02-4
Synonymes
3-Bromopropanal 1,2-ethanediol acetal
3-Bromopropionaldehyde ethylene acetal

Conditionnement Prix ($) Quantité Disponibilité
10g 38,70
50g 128,00
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2-(2-Bromoethyl)-1,3-dioxolane, 95%, stab. with silver

MDL
MFCD00003216
EINECS
242-551-1

Propriétés chimiques

Formule
C5H9BrO2
Poids moleculaire
181.04
Point d'ébullition
68-70°/8mm
Point d'éclair
65°(149°F)
Densité
1.512
Indice de réfraction
1.4790
Sensibilité
Light Sensitive
Solubilité
It is immiscible with water.

Applications

2-(2-Bromoethyl)-1,3-dioxolane is used as a pharmaceutical intermediate, dioxolanes, acetals, ketals, building blocks, chemical synthesis, organic building blocks and oxygen compounds. 1,1-(Ethylenedioxy)-3-bromopropane is used in the synthesis of EGFR inhibitors. Also used in the synthesis of orally active agents of cancer and cell proliferation with quinoline substructures. It is also used as flavouring agent.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8°C. Light sensitive. Store under inert gas.

Références bibliographiques

George Buechi.; Hans Wuest. Synthesis of (+-)-nuciferal. J. Org. Chem.196934, (4), 1122-1123.

Ehud Keinan.; Zeev Roth. Regioselectivity in organo-transition-metal chemistry. A new indicator substrate for classification of nucleophiles. J. Org. Chem.198348, (10), 1769-1772.

Masked ß-formylethyl synthon, compare preceding entry. The derived Grignard, which, unlike the dioxane analogue, is unstable above room temperature, shows similar attenuated reactivity in comparison with simple alkyl Grignard reagents, reacting with acid chlorides to give -ketoaldehydes without carbinol formation, and with enones to give, at low temperatures, predominantly the 1,4-addition product without the need for Cu catalysis:Tetrahedron Lett., 28, 3217 (1987).

The Grignard undergoes coupling reactions (CuBr2 + LiCl catalysis) with allylic halides: Tetrahedron Lett., 4549 (1979); J. Org. Chem., 46, 1504 (1981), allylic acetates: J. Am. Chem. Soc., 104, 2269 (1982), and primary alkyl bromides: J. Org. Chem., 48, 1767 (1983).

For a review of 3-carbon homologating reagents, including many examples of Grignard and organocuprate reactions of these molecules, see: Chem. Rev., 84, 409 (1984).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H227-H301-H315-H319-H335

Combustible liquid. Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Mentions de prudence: P210u-P261-P301+P310a-P305+P351+P338-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. IF SWALLOWED: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
103516
Classe de danger
6.1
Groupe d'emballage
III
Code tarifaire harmonisé
2932.99
TSCA
No

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