2,2-DIMETHYL-1,3-DIOXAN-5-ONE Chemical Properties

Boiling point:

40-46°C/14mm

Density 

1,09 g/cm³

refractive index 

1.4315

Flash point:

>110°C

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Water Solubility 

Miscible with water and most organic solvents.

Sensitive 

Air & Moisture Sensitive

BRN 

3061933

InChI

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

InChIKey

ASFQDNDZFGFMMP-UHFFFAOYSA-N

SMILES

O1CC(=O)COC1(C)C

CAS DataBase Reference

74181-34-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38

Safety Statements 

26-37/39-39-24/25

RIDADR 

1993

HazardClass 

3

PackingGroup 

III

HS Code 

29141900

2,2-DIMETHYL-1,3-DIOXAN-5-ONE Usage And Synthesis

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.

Synthesis

The general procedure for the synthesis of 2,2-dimethyl-1,3-dioxan-5-one from 5-amino-2,2-dimethyl-1,3-dioxan-5-methanol was as follows: first, 2,2-dimethoxypropane (21.5 mL, 175 mmol) and p-toluenesulfonic acid monohydrate (1.58 g, 7.93 mmol) were added to a solution of tris(hydroxymethyl)aminomethane ( 25.2 g, 159 mmol) in a solution of N,N-dimethylformamide (DMF, 180 mL). The reaction mixture was stirred at room temperature for 22 hours. After completion of the reaction, the mixture was diluted with ethyl acetate and neutralized with the addition of triethylamine. Subsequently, the solvent was concentrated under reduced pressure to remove the solvent and the crude product obtained was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate, 5:1) to afford 2,2-dimethyl-5-amino-5-hydroxymethyl-1,3-dioxane (20.9 g, 78% yield) as a colorless solid. The structure of this intermediate was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.80 (d, J = 12.0 Hz, 2H), 3.60 (d, J = 12.0 Hz, 2H), 3.53 (s, 2H), 2.61 (s, 2H), 1.45 (s, 3H), 1.41 (s, 3H). Next, the above intermediate (10.2 g, 62.1 mmol) was dissolved in water (60 mL) and potassium dihydrogen phosphate (KH2PO4, 8.51 g, 621 mmol) was added. An aqueous solution of sodium periodate (NaIO4) (0.5 M, 125 mL, 63 mmol) was slowly added dropwise at 0 °C. After completion of the dropwise addition, the reaction mixture was stirred for 1 h at room temperature. After completion of the reaction, the product was extracted with dichloromethane and the organic layer was washed sequentially with 5% aqueous sodium thiosulfate and saturated saline and dried over anhydrous sodium sulfate. Finally, the solvent was removed by concentration under reduced pressure to afford the target compound 2,2-dimethyl-1,3-dioxan-5-one (7.35 g, 91% yield) as a colorless oil. Its structure was confirmed by 1H NMR (400 MHz, CDCl3): δ 4.15 (s, 4H), 1.45 (s, 6H).

References

[1] Australian Journal of Chemistry, 2001, vol. 54, # 12, p. 769 - 776
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5891 - 5901
[3] Helvetica Chimica Acta, 2003, vol. 86, # 7, p. 2458 - 2470
[4] Synthesis, 1998, # 6, p. 879 - 882
[5] Canadian Journal of Chemistry, 1995, vol. 73, # 10, p. 1616 - 1626

2,2-DIMETHYL-1,3-DIOXAN-5-ONE(74181-34-3)Related Product Information

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