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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

Numéro CAS
1521-51-3
Synonymes
2-Cyclohexenyl bromide

Dimensions Prix ($) Quantité Disponibilité
5g 42,21
25g 162,90
100g 463,20
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3-Bromocyclohexene, 95%, stab. with 300-1000ppm Propylene oxide

MDL
MFCD00013775

Propriétés chimiques

Formule
C6H9Br
Poids formulaire
161.05
Point d'ébullition
64-65°/15mm
Point d'éclair
54°(129°F)
Densité
1.400
Indice de réfraction
1.5310
Solubilité
Not miscible or difficult to mix in water.

Applications

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.

Notes

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

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226-H315-H319-H335

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

Mentions de prudence: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. 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 INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
635953
Classe de danger
3
Groupe d'emballage
III
Code tarifaire harmonisé
2903.89
TSCA
No

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