82442-58-8

Basic information

• Product Name: (1S,2S)-(-)-trans-1,2-bis(hydroxymethyl)cyclobutane
• Synonyms: (1S,2S)-(-)-trans-1,2-bis(hydroxymethyl)cyclobutane
• CAS NO: 82442-58-8
• Molecular Weight: 116.16
• Mol File: 82442-58-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1S,2S)-(-)-trans-1,2-bis(hydroxymethyl)cyclobutane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(-)-trans-1,2-bis(hydroxymethyl)cyclobutane(82442-58-8)
• EPA Substance Registry System: (1S,2S)-(-)-trans-1,2-bis(hydroxymethyl)cyclobutane(82442-58-8)

Safety Data

• Hazardous Substances Data: 82442-58-8(Hazardous Substances Data)

Upstream product

• 10268-82-3 diethyl trans-1,2-cyclobutanedicarboxylate 
• 10268-82-3 diethyl cis-1,2-cyclobutanedicarboxylate 
• 2607-03-6 dimethyl cis-1,2-cyclobutanedicarboxylate 
• 3396-14-3 (RR,SS)-trans-1,2-cyclobutanedicarboxylic acid 
• 412346-70-4 1-cyano-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 869-10-3 diethyl 2,5-dibromoadipate 
• 7371-67-7 dimethyl trans-1,2-cyclobutane dicarboxylate 
• 1124-13-6 (+/-)-(1S,2S)-cyclobutane-1,2-dicarboxylic acid 
• 3396-17-6 trans-1,2-dicyanocyclobutane 
• 7371-64-4 trans-(cyclobutane-1,2-diyl)dimethanol 

Downstream Products

• 35630-06-9 trans-1,2-cyclobutanedimethanol, bis(toluenesulfonate) 
• 55659-54-6 (-)-(1R,2R)-1,2-bis(hydroxymethyl)cyclobutane 
• 82864-76-4 (1S,2S)-2-Hydroxymethyl-cyclobutanecarboxylic acid 
• 82390-72-5 (-)-(1R,2R)-trans-2-(hydroxymethyl)cyclobutanoic acid 
• 156198-56-0 (trans-cyclobutane-1,2-diyl)bis(methylene) bis(4-methylbenzenesulfonate) 

Relevant articles and documents

Understanding the Structure–Polymerization Thermodynamics Relationships of Fused-Ring Cyclooctenes for Developing Chemically Recyclable Polymers

Polymers that can be chemically recycled to their constituent monomers offer a promising solution to address the challenges in plastics sustainability through a circular use of materials. The design and development of monomers for next-generation chemical

Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds

Reversible cleavage of C(sp3)-H bonds can enable racemization or epimerization, offering a valuable tool to edit the stereochemistry of organic compounds. While epimerization reactions operating via cleavage of acidic C(sp3)-H bonds, such as the Cα-H of carbonyl compounds, have been widely used in organic synthesis and enzyme-catalyzed biosynthesis, epimerization of tertiary carbons bearing a nonacidic C(sp3)-H bond is much more challenging with few practical methods available. Herein, we report the first synthetically useful protocol for the epimerization of tertiary carbons via reversible radical cleavage of unactivated C(sp3)-H bonds with hypervalent iodine reagent benziodoxole azide and H2O under mild conditions. These reactions exhibit excellent reactivity and selectivity for unactivated 3° C-H bonds of various cycloalkanes and offer a powerful strategy for editing the stereochemical configurations of carbon scaffolds intractable to conventional methods. Mechanistic study suggests that the unique ability of N3? to serve as a catalytic H atom shuttle is critical to reversibly break and reform 3° C-H bonds with high efficiency and selectivity.