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

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

Uses

Used in Chemical Synthesis:
2,2-DIMETHYL-1,3-DIOXAN-5-ONE is used as a key intermediate in the preparation of 2,2-DIMETHYL-[1,3]DIOXAN-5-OL by reducing with lithium aluminum hydride. This reduction reaction allows for the synthesis of a variety of chemical compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
2,2-DIMETHYL-1,3-DIOXAN-5-ONE is used in the annulation of beta-(hetero)aryl-alfa-nitro-alfa,beta-enals, which are important building blocks in the synthesis of pharmaceutical compounds. This annulation process enables the development of new drugs with potential therapeutic benefits.

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

Upstream product

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

Downstream Products

• 126178-07-2 (S)-(+)-1-(2,2-dimethyl-1,3-dioxan-5-ylidenamino)-2-methoxymethylpyrrolidine 
• 126178-08-3 N-(2,2-Dimethyl-1,3-dioxan-5-ylidene)-N-[(2'R)-2-(methoxymethyl)tetrahydro-1'H-1'-pyrrolyl]amine 
• 90602-90-7 benzyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2-formylamino-acetate 
• 123176-36-3 diphenylmethyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2-formylamino-acetate 
• 175984-08-4 2,2-dimethyl-4H-1,3-dioxin-5-yl benzoate 
• 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 

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

Importance of the Electron Correlation and Dispersion Corrections in Calculations Involving Enamines, Hemiaminals, and Aminals. Comparison of B3LYP, M06-2X, MP2, and CCSD Results with Experimental Data

While B3LYP, M06-2X, and MP2 calculations predict the δG° values for exchange equilibria between enamines and ketones with similar acceptable accuracy, the M06-2X/6-311+G(d,p) and MP2/6-311+G(d,p) methods are required for enamine formation reactions (for example, for enamine 5a, arising from 3-methylbutanal and pyrrolidine). Stronger disagreement was observed when calculated energies of hemiaminals (N,O-acetals) and aminals (N,N-acetals) were compared with experimental equilibrium constants, which are reported here for the first time. Although it is known that the B3LYP method does not provide a good description of the London dispersion forces, while M06-2X and MP2 may overestimate them, it is shown here how large the gaps are and that at least single-point calculations at the CCSD(T)/6-31+G(d) level should be used for these reaction intermediates; CCSD(T)/6-31+G(d) and CCSD(T)/6-311+G(d,p) calculations afford δG° values in some cases quite close to MP2/6-311+G(d,p) while in others closer to M06-2X/6-311+G(d,p). The effect of solvents is similarly predicted by the SMD, CPCM, and IEFPCM approaches (with energy differences below 1 kcal/mol).

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.