107289-20-3

Basic information

• Product Name: (R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXIN-4-ONE
• Synonyms: (R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXIN-4-ONE;(R)-2-t-Butyl-6-methyl-4H-1,3-dioxin-4-one
• CAS NO: 107289-20-3
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.21
• Product Categories: Chiral Building Blocks;Lactones;Organic Building Blocks
• Mol File: 107289-20-3.mol

Chemical Properties

• Melting Point: 60-62 °C
• Boiling Point: 259.4°C at 760 mmHg
• Flash Point: 102.7°C
• Appearance: /
• Density: 1.047g/cm³
• Vapor Pressure: 0.013mmHg at 25°C
• Refractive Index: 1.457
• BRN: 4176869
• CAS DataBase Reference: (R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXIN-4-ONE(107289-20-3)
• EPA Substance Registry System: (R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXIN-4-ONE(107289-20-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 107289-20-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXIN-4-ONE is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the creation of complex organic molecules that can be tailored for specific therapeutic applications.
Used in Fine Chemicals Production:
In the fine chemicals industry, (R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXIN-4-ONE serves as a valuable building block for the production of specialty chemicals with specific properties and applications.
Used in Organic Chemistry Research:
(R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXIN-4-ONE is utilized as a fundamental component in organic chemistry research, where it contributes to the understanding of molecular interactions and the development of novel chemical reactions.
Used in Drug Discovery:
(R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXIN-4-ONE holds potential in medicinal chemistry for the development of new drugs and therapeutic agents, thanks to its ability to form complex organic molecules with potential biological activities.
Used as a Reagent in Chemical Reactions:
This dioxin derivative is also employed as a reagent in various chemical reactions, facilitating the formation of complex organic molecules that are essential in the creation of new compounds with specific applications across different industries.

InChI:InChI=1/C9H14O3/c1-6-5-7(10)12-8(11-6)9(2,3)4/h5,8H,1-4H3/t8-/m1/s1

Upstream product

• 100017-18-3 (2R,6R)-2-tert-butyl-6-methyl-1,3-dioxan-4-one 
• 630-19-3 pivalaldehyde 

Downstream Products

• 119620-09-6 (2'R,3R)-4-(2'-tert-Butyl-4'-oxo-4'H-1',3'-dioxin-6'-yl)-3-phenylbutyraldehyd 
• 119620-08-5 (S)-4-((R)-2-tert-Butyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-phenyl-butyraldehyde 
• 119620-04-1 (3'E,2R,2'RS)-2-tert-Butyl-6-(2'-hydroxy-4'-phenyl-3'-butenyl)-4H-1,3-dioxin-4-on 
• 119620-05-2 (R)-2-tert-Butyl-6-((E)-(R)-2-hydroxy-4-phenyl-but-3-enyl)-[1,3]dioxin-4-one 
• 119620-00-7 (R)-2-tert-Butyl-6-[(S)-2-hydroxy-2-(2,4,6-trimethyl-phenyl)-ethyl]-[1,3]dioxin-4-one 
• 119620-01-8 (R)-2-tert-Butyl-6-[(R)-2-hydroxy-2-(2,4,6-trimethyl-phenyl)-ethyl]-[1,3]dioxin-4-one 
• 119619-92-0 (R)-2-tert-Butyl-6-((S)-3,3,3-trifluoro-2-hydroxy-2-phenyl-propyl)-[1,3]dioxin-4-one 
• 119619-93-1 (R)-2-tert-Butyl-6-((R)-3,3,3-trifluoro-2-hydroxy-2-phenyl-propyl)-[1,3]dioxin-4-one 
• 119619-94-2 (R)-2-tert-Butyl-6-[(S)-2-hydroxy-2-(4-nitro-phenyl)-ethyl]-[1,3]dioxin-4-one 
• 119619-95-3 (R)-2-tert-Butyl-6-[(R)-2-hydroxy-2-(4-nitro-phenyl)-ethyl]-[1,3]dioxin-4-one 
• 100017-18-3 (2R,6R)-2-tert-butyl-6-methyl-1,3-dioxan-4-one 
• 107289-28-1 (2R,2'S)-2-tert-Butyl-6-(2'-hydroxy-2'-phenylethyl)-4H-1,3-dioxin-4-on 
• 107289-27-0 (R)-2-tert-Butyl-6-((R)-2-hydroxy-2-phenyl-ethyl)-[1,3]dioxin-4-one 
• 107289-24-7 (2R)-2-(tert-butyl)-6-ethyl-2H,4H-1,3-dioxin-4-one 

Relevant articles and documents

Modified preparation of (2R)-2-tert-butyl-6-methyl-4H-1,3-dioxin-4-one; a chiral acetylacetic acid derivative for the synthesis of enantiopure compounds

An improved synthesis of the title compound in ca. 45% yield on up to a 174 mmol scale is reported. Bromination of (2R,6R)-2-tert-butyl-6-methyl-1,3-dioxan-4-one gives a mixture of mono- and dibromides which must be purified by chromatography to remove impurities which may poision the palladium catalyst in the following dehalogenation step.

104. Bromination of Cyclic Acetals from α-Amino Acids and α- or β-Hydroxy Acids with N-Bromosuccinimide

The preparation of novel electrophylic building blocks for the synthesis of enantiomerically pure compounds (EPC) is described.Thus, the 2-(tert-butyl)dioxolanones, -oxazolidinones, -imidazolidinones, and -dioxanones obtained by acetalization of pivalalde

123. 1,3-Dioxanone Derivatives from β-Hydroxy-carboxylic Acids and Pivalaldehyde. Versatile Buiding Blocks for Syntheses of Enantiomerically Pure Compounds. A Chiral Acetoacetic Acid Derivative

(R)-3-Hydroxybutyric acid (from the biopolymer PHB) and pivalaldehyde give the crystalline cis- or (R,R)-2-(tert-butyl)-6-methyl-1,3-dioxan-4-one (1a), the enolate of which is stable at low temperature in THF solution and can be alkylated diastereoselectively (->3, 4, 5, and 7).Phenylselenation and subsequent elimination give an enantiomerically pure enol acetal 10 of aceto-acetic acid.Some reactions of 10 have been carried out, such as Michael addition (->11), alkylation on the CH3 substituent (->13), hydrogenation of the C=C bond (->1a) and photochemical cycloaddition (->16).The overall reactions are substitutions on the one sterogenic center of the starting β-hydroxy acid without racemization and without using a chiral auxiliary.