55659-54-6

Basic information

• Product Name: [1R,2R,(-)]-1,2-Cyclobutanedimethanol
• Synonyms: (-)-trans-1,2-Cyclobutanedimethanol;[1R,2R,(-)]-1,2-Cyclobutanedimethanol;1,2-Cyclobutanedimethanol, trans-
• CAS NO: 55659-54-6
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.1583
• Mol File: 55659-54-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 250.4°Cat760mmHg
• Flash Point: 123.1°C
• Appearance: /
• Density: 1.074g/cm³
• Vapor Pressure: 0.00344mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: [1R,2R,(-)]-1,2-Cyclobutanedimethanol(CAS DataBase Reference)
• NIST Chemistry Reference: [1R,2R,(-)]-1,2-Cyclobutanedimethanol(55659-54-6)
• EPA Substance Registry System: [1R,2R,(-)]-1,2-Cyclobutanedimethanol(55659-54-6)

Safety Data

• Hazardous Substances Data: 55659-54-6(Hazardous Substances Data)

Usage

Description

[1R,2R,(-)]-1,2-Cyclobutanedimethanol is a cycloalkane derivative with the molecular formula C6H12O2, belonging to the class of diols, which are compounds containing two hydroxyl groups. This chiral chemical exists as two enantiomers, (1R,2R) and (1S,2S), and is characterized by its unique physical and chemical properties that make it a valuable building block for the synthesis of various complex organic molecules.

Uses

Used in Organic Synthesis:
[1R,2R,(-)]-1,2-Cyclobutanedimethanol is used as a reagent in organic synthesis for the preparation of cyclic lactones and other organic compounds. Its unique structure and properties allow for the creation of a wide range of complex molecules, making it a versatile component in the field of organic chemistry.
Used in Polymer Production:
In the polymer industry, [1R,2R,(-)]-1,2-Cyclobutanedimethanol is used as a building block for the development of new polymers. Its incorporation into polymer structures can lead to materials with enhanced properties, such as improved strength, flexibility, or chemical resistance.
Used in Pharmaceutical Industry:
[1R,2R,(-)]-1,2-Cyclobutanedimethanol has potential applications in the production of pharmaceuticals. Its unique structure and properties can be utilized in the synthesis of new drugs or drug candidates, contributing to the development of novel therapeutic agents for various medical conditions.

InChI:InChI=1/C6H12O2/c7-3-5-1-2-6(5)4-8/h5-8H,1-4H2

Upstream product

• 54445-64-6 (1R,2S)-(2-hydroxymethylcyclobutyl)methanol 
• 17224-72-5 (1R,2R)-(-)-trans-1,2-cyclobutanedicarboxylic acid 
• 3396-17-6 trans-1,2-dicyanocyclobutane 
• 412346-70-4 1-cyano-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 82390-72-5 (-)-(1R,2R)-trans-2-(hydroxymethyl)cyclobutanoic acid 
• 7371-64-4 trans-(cyclobutane-1,2-diyl)dimethanol 
• 2607-03-6 dimethyl cis-1,2-cyclobutanedicarboxylate 
• 3396-14-3 (RR,SS)-trans-1,2-cyclobutanedicarboxylic acid 
• 869-10-3 diethyl 2,5-dibromoadipate 
• 10268-82-3 diethyl cis-1,2-cyclobutanedicarboxylate 
• 7371-67-7 dimethyl trans-1,2-cyclobutane dicarboxylate 
• 1124-13-6 (+/-)-(1S,2S)-cyclobutane-1,2-dicarboxylic acid 
• 10268-82-3 diethyl trans-1,2-cyclobutanedicarboxylate 
• 4462-96-8 cis-1,2-cyclobutane dicarboxylic anhydride 

Downstream Products

• 82442-58-8 (1S,2S)-(-)-trans-1,2-bis(hydroxymethyl)cyclobutane 
• 82864-76-4 (1S,2S)-2-Hydroxymethyl-cyclobutanecarboxylic acid 
• 82390-72-5 (-)-(1R,2R)-trans-2-(hydroxymethyl)cyclobutanoic acid 
• 35630-06-9 trans-1,2-cyclobutanedimethanol, bis(toluenesulfonate) 

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.

Enzymes in Organic Synthesis. 24. Preparations of Enantiomerically Pure Chiral Lactones via Stereospecific Horse Liver Alcohol Dehydrogenase Catalyzed Oxidations of Monocyclic Meso Diols

Preparative-scale horse liver alcohol dehydrogenase catalyzed oxidation of monocyclic meso diols provides a direct and convenient one-step route to a broad range of chiral γ-lactones of value as synthons in asymmetric synthesis.The general applicability of the method is demonstrated by oxidations of cis-1,2-bis(hydroxymethyl) substrates of the cyclohexyl, cyclohexenyl, cyclopentyl, cyclobutyl, cyclopropyl, and dimethylcyclopropyl series.For each diol, oxidation of the hydroxymethyl group attached to the S chiral center occurs exclusively, and the pure γ-lactone products are isolated in high (68-90percent) yields and of 100percent ee.In contrast, the enzyme does not exhibit significant enantiomeric selectivity in its catalysis of oxidations of the corresponding racemic trans diols.The stereospecificities observed, or lack thereof, are as predicted by the active-site model.