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
Price (EUR)
Quantity
-

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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    Safety and Handling


    Classification of the substance or mixture
    CLP classification - Regulation(EC) No 1272/2008
    Flammable liquids
    Category 3
    Skin Corrosion/Irritation
    Category 2
    Serious Eye Damage/Eye Irritation
    Category 2
    Specific target organ toxicity - (single exposure)
    Category 3
    Label Elements
    Signal Word

    Warning

    Hazard Statements

    H315 - Causes skin irritation

    H319 - Causes serious eye irritation

    H335 - May cause respiratory irritation

    Physical Hazards

    H226 - Flammable liquid and vapor

    Precautionary Statements

    P210 - Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking

    P280 - Wear protective gloves/protective clothing/eye protection/face protection

    P302 + P352 - IF ON SKIN: Wash with plenty of soap and water

    P304 + P340 - IF INHALED: Remove person to fresh air and keep comfortable for breathing

    P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing

    P312 - Call a POISON CENTER or doctor if you feel unwell