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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

Número CAS
18742-02-4
Nombre Alternativo
3-Bromopropanal 1,2-ethanediol acetal
3-Bromopropionaldehyde ethylene acetal

Tamaño Precio ($) Cantidad Disponibilidad
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

Propiedades químicas

Fórmula
C5H9BrO2
Peso molecular
181.04
Punto de ebullición
68-70°/8mm
Punto de inflamabilidad
65°(149°F)
Densidad
1.512
Índice de refracción
1.4790
Sensibilidad
Light Sensitive
Solubilidad
It is immiscible with water.

Aplicaciones

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.

Notas

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.

Referencias documentales

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).

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H227-H301-H315-H319-H335

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

Indicaciones de precaución: P210u-P261-P280a-P280a-P301+P310a-P305+P351+P338-P304+P340-P312a-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF SWALLOWED: 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
103516
Clase de peligro
6.1
Grupo de embalaje
III
Código de tarifa arancelaria unificado
2932.99
TSCA
No

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