Thermo Scientific Chemicals

3-Bromocyclohexene, 95%, Thermo Scientific Chemicals

Catalog number: A10370.06
5 g, Each
Thermo Scientific Chemicals

3-Bromocyclohexene, 95%, Thermo Scientific Chemicals

Catalog number: A10370.06
5 g, Each
Quantity
Catalog number: A10370.06
also known as A10370-06
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Chemical Identifiers

CAS
1521-51-3
IUPAC Name
3-bromocyclohex-1-ene
Molecular Formula
C6H9Br
InChI Key
AJKDUJRRWLQXHM-UHFFFAOYNA-N
SMILES
BrC1CCCC=C1
Appearance (Color)
Clear colorless to yellow to brown
Form
Liquid
Assay (GC)
≥94.0%
Comment
May darken on storage
Refractive Index
1.5280-1.5340 @ 20?C

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.
RUO – Research Use Only

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