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3-Bromocyclohexene, 95%, Thermo Scientific Chemicals

173.87 EUR - 650.00 EUR

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
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Thermo Scientific Alfa Aesar
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Description

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.
Specifications
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Safety and Handling

Safety and Handling

GHS H Statement
H226-H315-H319-H335
Flammable liquid and vapor.
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.

P210-P233-P240-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P363-P374-P380-P501c

H226-H315-H319-H335

missing translation for 'dotInformation' : Transport Hazard Class: 3; Packing Group: III; Proper Shipping Name: FLAMMABLE LIQUIDS, N.O.S.

missing translation for 'tsca' : No

Recommended Storage : Keep cold

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