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

CAS Number
1521-51-3
Synonyms
2-Cyclohexenyl bromide

Stock No. Size Price ($) Quantity Availability
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

Chemical Properties

Formula
C6H9Br
Formula Weight
161.05
Boiling Point
64-65°/15mm
Flash Point
54°(129°F)
Density
1.400
Refractive Index
1.5310
Storage & Sensitivity
Keep Cold.
Solubility
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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H315-H319-H335

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

Precautionary Statements: 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

Other References

Beilstein
635953
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2903.89
TSCA
No

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