74181-34-3

Basic information

• Product Name: 2,2-DIMETHYL-1,3-DIOXAN-5-ONE
• Synonyms: AKOS 33;2,2-DIMETHYL-1,3-DIOXAN-5-ONE;2,2-DIMETHYL-1,3-DIOXANE-5-ONE;2,2-Dimethyl-1,3-dioxan-5-one, tech. 90%;2,2-Dimethyl-1,3-dioxan-5-one,99%;2,2-Dimethyl-1,3-dioxan-5-one,97%;2,2-Dimethyl-1,3-dioxan-5-one, technical, 90%
• CAS NO: 74181-34-3
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.14
• EINECS: -0
• Product Categories: Dioxanes;Dioxanes & Dioxolanes
• Mol File: 74181-34-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 40-46°C/14mm
• Flash Point: >110°C
• Appearance: clear yellow liquid
• Density: 1,09 g/cm3
• Vapor Pressure: 0.675mmHg at 25°C
• Refractive Index: 1.4315
• Storage Temp.: 0-10°C
• Water Solubility: Miscible with water and most organic solvents.
• Sensitive: Air & Moisture Sensitive
• BRN: 3061933
• CAS DataBase Reference: 2,2-DIMETHYL-1,3-DIOXAN-5-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYL-1,3-DIOXAN-5-ONE(74181-34-3)
• EPA Substance Registry System: 2,2-DIMETHYL-1,3-DIOXAN-5-ONE(74181-34-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-37/39-39-24/25
• RIDADR: 1993
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 74181-34-3(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Uses

2,2-Dimethyl-1,3-dioxan-5-one is used in the preparation of 2,2-dimethyl-[1,3]dioxan-5-ol by reducing with lithium aluminum hydride. It is also used in the annulation of bete-(hetero)aryl-alfa-nitro-alfa,beta-enals.

InChI:InChI=1/C6H10O3/c1-6(2)8-3-5(7)4-9-6/h3-4H2,1-2H3

Upstream product

• 87696-33-1 (S)-2-(O-tert-butyldiphenylsilyloxy)propanal 
• 108-94-1 cyclohexanone 
• 1355016-92-0 C₂₇H₃₇NO₃Si 

Downstream Products

• 330435-58-0 2,2-dimethyl-4H-1,3-dioxin-5-yl trifluoromethanesulfonate 
• 850426-80-1 (3S,4S)-4-p-nitrophenyl-1,3,4-trihydroxy-1,3-O-isopropylidene-butan-2-one 
• 856451-74-6 1-(5-hydroxy-2,2-dimethyl-[1,3]dioxan-5-yl)-3-methylene-cyclohexanecarboxylic acid 
• 371153-91-2 cyclohexyl-(2,2-dimethyl-[1,3]dioxan-5-ylidene)-amine 

Relevant articles and documents

Further insights into the organocatalytic reaction of 2,2-dimethyl-1,3-dioxan-5-one with α-silyloxy aldehydes

Proline-catalysed reactions of dihydroxyacetone isopropylidene acetal, 1, with enantiopure α-silyloxy aldehydes 2/4/6/8 afford 90–95% yields of cross-aldol products (only one stereoisomer in each case), provided that 15 ± 10 equiv of H2O are pr

Relative tendency of carbonyl compounds to form enamines

Equilibria between carbonyl compounds and their enamines (from O-TBDPS-derived prolinol) have been examined by NMR spectroscopy in DMSO-d 6. By comparing the exchange reactions between pairs (enamine A + carbonyl B → carbonyl A + enamine B), a quite general scale of the tendency of carbonyl groups to form enamines has been established. Aldehydes quickly give enamines that are relatively more stable than those of ketones, but there are exceptions to this expected rule; for example, 1,3-dihydroxyacetone acetals or 3,5-dioxacyclohexanones (2-phenyl-1,3-dioxan-5-one and 2,2-dimethyl-1,3- dioxan-5-one) show a greater tendency to afford enamines than many α-substituted aldehydes.