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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

Codice CAS
1521-51-3
Sinonimi
2-Cyclohexenyl bromide

Dimensioni Prezzo ($) Quantità Disponibilità
5g 42,20
25g 163,00
100g 521,00
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3-Bromocyclohexene, 95%, stab. with 300-1000ppm Propylene oxide

MDL
MFCD00013775

Proprietà chimiche

Formula
C6H9Br
Peso formula
161.05
Punto di ebollizione
64-65°/15mm
Punto di infiammabilità
54°(129°F)
Densità
1.400
Indice di rifrazione
1.5310
Solubilità
Not miscible or difficult to mix in water.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H226-H315-H319-H335

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

Dichiarazioni precauzionali: 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.

Altri riferimenti

Beilstein
635953
Classe di rischio
3
Gruppo di imballaggio
III
Codice tariffe armonizzato
2903.89
TSCA
No

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