76215-48-0

Basic information

• Product Name: 1-chloro-3,3-bis(trifluoromethyl)-1,3-dihydro-1lambda~3~,2-benziodoxole
• CAS NO: 76215-48-0
• Molecular Formula: C₉H₄ClF₆IO
• Molecular Weight: 404.4753
• Mol File: 76215-48-0.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 1-chloro-3,3-bis(trifluoromethyl)-1,3-dihydro-1lambda~3~,2-benziodoxole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-3,3-bis(trifluoromethyl)-1,3-dihydro-1lambda~3~,2-benziodoxole(76215-48-0)
• EPA Substance Registry System: 1-chloro-3,3-bis(trifluoromethyl)-1,3-dihydro-1lambda~3~,2-benziodoxole(76215-48-0)

Safety Data

• Hazardous Substances Data: 76215-48-0(Hazardous Substances Data)

Usage

Structure

Benziodoxole ring with a chlorine atom and two trifluoromethyl groups attached

Usage

Reagent in organic synthesis

Specific Applications

a. Conversion of alcohols to aldehydes and ketones
b. Oxidation of various functional groups (sulfides, amines)

Reactivity

Highly reactive and versatile

Advantages

a. Less toxic or hazardous compared to other oxidizing agents
b. Stability
c. Ease of handling

Popularity

Widely used in organic chemistry laboratories

Upstream product

• 718-64-9 1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol 
• 70091-67-7 lithium 1,1,1,3,3,3-hexafluoro-2-(2-lithiophenyl)-2-propoxide 
• 76215-47-9 1,1,1,3,3,3-hexafluoro-2-(2-iodophenyl)-propan-2-ol 

Relevant articles and documents

Cys–Cys and Cys–Lys Stapling of Unprotected Peptides Enabled by Hypervalent Iodine Reagents

Easy access to a wide range of structurally diverse stapled peptides is crucial for the development of inhibitors of protein-protein interactions. Herein, we report bis-functional hypervalent iodine reagents for two-component cysteine-cysteine and cysteine-lysine stapling yielding structurally diverse thioalkyne linkers. This stapling method works with unprotected natural amino acid residues and does not require pre-functionalization or metal catalysis. The products are stable to purification and isolation. Post-stapling modification can be accessed via amidation of an activated ester, or via cycloaddition onto the formed thioalkyne group. Increased helicity and binding affinity to MDM2 was obtained for a i,i+7 stapled peptide.

Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines

A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp2)-H functionalization of alkenes, offering 26 enynes in 62-92% yield with excellent functional group tolerance.

Practical synthesis of α,β-Alkynyl ketones by oxidative alkynylation of aldehydes with hypervalent alkynyliodine reagents

A practical, metal-free carbonyl C(sp2)H oxidative alkynylation of aldehydes with hypervalent alkynyliodine reagents without the use of any catalysts is described for the synthesis of various α,β-alkynyl ketones. Here, two different methods have been developed where limiting reagents or substrates can be switched, and adopted according to the valuableness of aldehyde substrates or hypervalent alkynyliodine reagents. These reactions proceed with a broad substrate scope and high functional-group compatibility.