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1521-51-3 - 3-Bromocyclohexene, 95%, stab. with 300-1000ppm Propylene oxide - 2-Cyclohexenyl bromide - A10370 - Alfa Aesar

A10370 3-Bromocyclohexene, 95%, stab. with 300-1000ppm Propylene oxide

Número CAS
1521-51-3
Nombre Alternativo
2-Cyclohexenyl bromide

Tamaño Precio ($) Cantidad Disponibilidad
5g 42,20
25g 163,00
100g 521,00
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3-Bromocyclohexene, 95%, stab. with 300-1000ppm Propylene oxide

MDL
MFCD00013775

Propiedades químicas

Fórmula
C6H9Br
Peso molecular
161.05
Punto de ebullición
64-65°/15mm
Punto de inflamabilidad
54°(129°F)
Densidad
1.400
Índice de refracción
1.5310
Solubilidad
Not miscible or difficult to mix in water.

Aplicaciones

In peptide synthesis, can be used to protect the hydroxyl group of serine and threonine as the cyclohexyl (Chx) ether, by reaction with the sodium alkoxide (generated with NaH), followed by hydrogenation. The group is stable to TFA and 20% piperidine in DMF, but can be cleaved with TfOH in TFA, in the presence of thioanisole as a cation scavenger. It is also used in the synthesis of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine.1 It was also used in the synthesis of enantiopure cyclohexitols such as muco-quercitol, D-chiro-inocitol and allo-inocitol.

Notas

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

Referencias documentales

Y Nishiyama, et al. An efficient synthesis of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine.Chem Pharm Bull (Tokyo).,2001,49(2), 233-5.

Lee YJ, et al.Synthesis of enantiopure cyclitols from (±)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S, S)-hydrobenzoin and (S)-mandelic acid as chiral sources.Tetrahedron.,2005,61(8), 1987-2001.

In peptide synthesis, can be used to protect the hydroxyl group of serine and threonine as the cyclohexyl (Chx) ether, by reaction with the sodium alkoxide (generated with NaH), followed by hydrogenation. The group is stable to TFA and 20% piperidine in DMF, but can be cleaved with TfOH in TFA, in the presence of thioanisole as a cation scavenger: J. Chem. Soc., Perkin 1, 1949 (2000). See Appendix 6.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H226-H315-H319-H335

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Indicaciones de precaución: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
635953
Clase de peligro
3
Grupo de embalaje
III
Código de tarifa arancelaria unificado
2903.89
TSCA
No

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