113428-57-2

Basic information

• Product Name: 2,2-DIMETHYL-4(S)-4-BROMOMETHYL-1,3-DIOXALANE
• Synonyms: 2,2-DIMETHYL-4(S)-4-BROMOMETHYL-1,3-DIOXALANE;(4S)-4-(BROMOMETHYL)-2 2-DIMETHYL-1 3-D&;1,3-Dioxolane,4-(bromomethyl)-2,2-dimethyl-,(4S)-(9CI);(4S)-2,2-Dimethyl-4-bromomethyl-1,3-dioxolane
• CAS NO: 113428-57-2
• Molecular Formula: C₆H₁₁BrO₂
• Molecular Weight: 195.05
• Product Categories: HALOMETYL
• Mol File: 113428-57-2.mol

Chemical Properties

• Boiling Point: 192.2°C at 760 mmHg
• Flash Point: 74.8°C
• Appearance: /
• Density: 1.359g/cm³
• Vapor Pressure: 0.688mmHg at 25°C
• Refractive Index: 1.453
• CAS DataBase Reference: 2,2-DIMETHYL-4(S)-4-BROMOMETHYL-1,3-DIOXALANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYL-4(S)-4-BROMOMETHYL-1,3-DIOXALANE(113428-57-2)
• EPA Substance Registry System: 2,2-DIMETHYL-4(S)-4-BROMOMETHYL-1,3-DIOXALANE(113428-57-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 113428-57-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,2-DIMETHYL-4(S)-4-BROMOMETHYL-1,3-DIOXALANE is used as a synthetic intermediate for the development of pharmaceuticals due to its ability to facilitate the creation of complex organic molecules. The bromomethyl group serves as a key reactive site, allowing for further chemical modifications that can enhance the compound's therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 2,2-DIMETHYL-4(S)-4-BROMOMETHYL-1,3-DIOXALANE is utilized as a versatile building block for the construction of diverse organic compounds. Its unique structure and reactivity contribute to the synthesis of a wide range of molecules, including those with potential applications in various industries such as materials science, agrochemicals, and specialty chemicals.
Used in Research and Development:
2,2-DIMETHYL-4(S)-4-BROMOMETHYL-1,3-DIOXALANE is also employed in research and development settings, where it can be explored for its potential in new chemical reactions and the discovery of novel compounds. Its properties and reactivity make it a valuable tool for scientists working on the frontiers of chemical innovation.

InChI:InChI=1/C6H11BrO2/c1-6(2)8-4-5(3-7)9-6/h5H,3-4H2,1-2H3/t5-/m1/s1

Upstream product

• 137490-63-2 (S)-(+)-3-bromo-1,2-propanediol 
• 77-76-9 2,2-dimethoxy-propane 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 4704-77-2 1-bromo-2,3-propanediol 

Downstream Products

• 4704-77-2 (R)-3-bromo-propane-1,2-diol 
• 1262760-10-0 (R)-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)cyclopropane-1-sulfonamide 
• 204129-78-2 methyl N-[(4-methoxyphenyl)sulfonyl]-S-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-D-penicillamine 

Relevant articles and documents

Chiral calix-salen cobalt complexes, catalysts for the enantioselective dynamic hydrolytic kinetic resolution of epibromohydrin

New calix-salen cobalt (III) complexes were synthesized as a mixture and as pure trimer or tetramer complexes. These cyclic complexes were used as catalysts to promote the dynamic hydrolytic kinetic resolution (HKR) of epibromohydrin in order to evaluate the effect of the cyclic structures size on the cooperative bimetallic interactions. Since the obtained catalysts were easily recovered from the reaction mixture by simple filtration, their efficiency was evaluated in recycling procedures. It was found that both cyclic oligomer complexes (trimer and tetramer) and the mixture of calix-salen complexes delivered the expected diol with high enantioselectivity and yield. Tetramer calix-salen cobalt complex proved to be the most active and selective catalyst of the series. In this case, an optimal conformation to allow the formation of bimetallic species activating respectively both the epoxide and water as nucleophile is probably responsible for an efficient dual activation.

Calix[8]arene as New Platform for Cobalt-Salen Complexes Immobilization and Use in Hydrolytic Kinetic Resolution of Epoxides

Eight cobalt-salen complexes have been covalently attached to a calix[8]arene platform through a flexible linker by a procedure employing Click chemistry. The corresponding well-defined catalyst proved its efficiency in the hydrolytic kinetic resolution (HKR) of various epoxides through an operative bimetallic cooperative activation, demonstrating highly enhanced activity when compared to its monomeric analogue. As an insoluble complex, this multisite cobalt-salen catalyst could be easily recovered and reused in successive catalytic runs. Products were isolated by a simple filtration with virtually no cobalt traces and without requiring a prior purification by flash chromatography.

Mixing and matching chiral cobalt- and manganese-based calix-salen catalysts for the asymmetric hydrolytic ring opening of epoxides

Homochiral oligomeric salen macrocycles possessing aromatic spacers have been prepared as new calix-salen derivatives. The corresponding cobalt and manganese complexes were synthesized and characterized, and their catalytic activities have been studied in the challenging hydrolysis of meso epoxides. While manganese calix-salen complexes were not active in the studied reactions, the dual heterobimetallic system, using an equimolar combination of cobalt and manganese calix-salen derivatives proved to be more enantioselective than the sole cobalt system. Furthermore, as heterogeneous complexes, the catalytic mixture could be easily recovered by simple filtration and successfully reengaged in subsequent catalytic runs. Interestingly, no need for cobalt reactivation was noticed to maintain maximum efficiency of this dual system. The matched Co/Mn dual catalyst was also used to promote the dynamic hydrolytic kinetic resolution of epibromohydrin.

Heterobimetallic dual-catalyst systems for the hydrolytic kinetic resolution of terminal epoxides

A heterobimetallic dual-catalyst system based on the preparation and use of various salen complexes has been developed for the hydrolytic kinetic resolution (HKR) of terminal epoxides. A combination of cobalt-salen and manganese-salen complexes, generated from ligands with the same configuration possessing thiophene or pyrrole moieties, produced indeed highly selective catalysts for the hydrolysis of epibromohydrin. This effect could also be extended to other terminal epoxides and to the more challenging ring opening of cyclohexene oxide. Kinetic studies indicated that only one CoIII salen complex was involved in the rate-determining step, which supported a heterobimetallic highly enantioselective pathway based on the crucial existence of in situ generated CoIII-OH species, previously postulated in the literature. The beneficial effect of the presence of additional Mn-complexes was ascribed to the inhibition of the alternative less enantioselective monometallic reaction pathway by epoxide activation.

Hydrolytic kinetic resolution of epoxides catalyzed by chromium(III)-endo, endo-2,5-diaminonorbornane-salen [Cr(III)-DIANANE-salen] complexes. Improved activity, low catalyst loading

The hydrolytic kinetic resolution (HKR) of terminal epoxides, using chiral chromium(III)-salen catalysts based on DIANANE (endo,endo-2,5-diaminonorbornane) , was studied. A broad substrate scope was found for the chromium(III)-DIANANE catalysts, and very low loadings (down to 0.05 mol%) were needed to achieve high enantiomeric purities of both the remaining epoxides and the product diols (up to >99% ee). Besides monosubstituted epoxides, 2-methyl-2-n-pentyloxirane, which is an example for 2,2-disubstituted epoxides, could be ring-opened in an asymmetric fashion with water in the presence of an electronically tuned chromium-(III)-DIANANE complex.