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3-Bromocyclohexene, 95%
CAS: 1521-51-3 | C6H9Br | 161.042 g/mol
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Catalog number A10370.14
also known as A10370-14
Price (TWD)
-
Quantity:
25 g
Chemical Identifiers
CAS1521-51-3
IUPAC Name3-bromocyclohex-1-ene
Molecular FormulaC6H9Br
InChI KeyAJKDUJRRWLQXHM-UHFFFAOYNA-N
SMILESBrC1CCCC=C1
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Specifications
Specification Sheet
Specification SheetAppearance (Color)Clear colorless to yellow to brown
FormLiquid
Assay (GC)≥94.0%
CommentMay darken on storage
Refractive Index1.5280-1.5340 @ 20?C
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Not miscible or difficult to mix in water.
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
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.
Solubility
Not miscible or difficult to mix in water.
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
RUO – Research Use Only
General 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.