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

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

Stock No. Conditionnement Prix ($) Quantité Disponibilité
A10370-06 5g 38,60
A10370-14 25g 167,00
A10370-22 100g 532,00
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3-Bromocyclohexene, 95%, stab. with 300-1000ppm Propylene oxide

MDL
MFCD00013775

Propriétés chimiques

Formule
C6H9Br
Poids moleculaire
161.05
Point d'ébullition
64-65°/15mm
Point d'éclair
54°(129°F)
Densité
1.400
Indice de réfraction
1.5310
Storage & Sensitivity
Keep Cold.
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-P233-P240-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P363-P374-P380-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. Fight fire with normal precautions from a reasonable distance. Evacuate area. Dispose of contents/ container to an approved waste disposal plant

Autres références

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

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