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  7. 3-Bromocyclohexene, 95%, Thermo Scientific Chemicals

3-Bromocyclohexene, 95%, Thermo Scientific Chemicals

Product Code. 11434183
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Quantity:
5 g
25 g
100 g
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Description

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.
TRUSTED_SUSTAINABILITY

Chemical Identifiers

CAS 1521-51-3
Molecular Formula C6H9Br
Molecular Weight (g/mol) 161.042
MDL Number MFCD00013775
InChI Key AJKDUJRRWLQXHM-UHFFFAOYSA-N
Synonym 3-bromocyclohex-1-ene, cyclohexene, 3-bromo, 1-bromo-2-cyclohexene, 3-bromo-1-cyclohexene, 1,2,3,4-tetrahydrobromobenzene, 3-bromo-cyclohexene, 2-cyclohexenyl bromide, 2-cyclohexen-1-yl bromide, 3-bromo cyclohexene, 3-bromanylcyclohexene
PubChem CID 137057
IUPAC Name 3-bromocyclohexene
SMILES C1CC=CC(C1)Br

Specifications

Density 1.4
Boiling Point 64°C to 65°C (15 mmHg)
Flash Point 54°C (129°F)
Refractive Index 1.531
Quantity 5 g
UN Number UN1993
Beilstein 635953
Solubility Information Not miscible or difficult to mix in water.
Formula Weight 161.05
Percent Purity 95%
Chemical Name or Material 3-Bromocyclohexene, Stabilized with 300 to 1000ppm Propylene oxide
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