2,6-Dimethyl-4H-pyran-4-one Chemical Properties

Melting point:

133-137 °C(lit.)

Boiling point:

248-250 °C(lit.)

Density 

0.9953

refractive index 

1.5300 (estimate)

Flash point:

248-250°C

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder or Crystals

color 

White to beige

Water Solubility 

Slightly soluble in water.

BRN 

107418

InChI

1S/C7H8O2/c1-5-3-7(8)4-6(2)9-5/h3-4H,1-2H3

InChIKey

VSYFZULSKMFUJJ-UHFFFAOYSA-N

SMILES

CC1=CC(=O)C=C(C)O1

LogP

0.100

CAS DataBase Reference

1004-36-0(CAS DataBase Reference)

NIST Chemistry Reference

4H-Pyran-4-one, 2,6-dimethyl-(1004-36-0)

EPA Substance Registry System

2,6-Dimethyl-4H-pyran-4-one (1004-36-0)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36/37

WGK Germany 

3

RTECS 

UQ0780000

HS Code 

29329995

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

MSDS

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2,6-Dimethyl-4H-pyran-4-one Usage And Synthesis

Chemical Properties

2,6-Dimethyl-4H-pyran-4-one is white to beige crystalline powder or crystals

Uses

2,6-Dimethyl-4-pyrone is used as a chemical and organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field.

Uses

2,6-Dimethyl-4H-pyran-4-one is used as a fragrance ingredient.

Reactions

2,6-dimethyl-4H-pyran-4-one reacts with Phosgene at room temperature could yield 2,6-bis(4′-chloro-2′,6′-dimethylphenyl)-4H-pyran-4-one, and 2-(4′-chloro-2′,6′-dimethylphenyl)-6-methyl-4H-pyran-4-one[1]. 

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 300, 1951 DOI: 10.1021/ja01145a098

Synthesis

Step 1: (DADC) 2 mg of the complex (1 equiv) was dissolved in dry pyridine (20% solution) and cooled in an external ice/water bath under N2. The corresponding acid chloride 3 (4.4 equiv) was added at 0-5 ??C and stirred at room temperature for 1-2 days. After ice/HCl (2N) hydrolysis, the mixture was repeatedly extracted with CH2Cl2. The bound organic layer was washed with satd. NaHCO3 solution, dried (Na2SO4), decolorized (charcoal), filtered and concentrated. Conversion of 1.00 g 1 (2.34 mmol) with acetyl chloride according to method B and chromatographic purification gave 0.58 g (46%) of 4a.13C NMR (50 MHz, CDCl3):??= 14.0 (q), 18.4 (q), 61.7 (t), 121.6, 164.0, 165.2, 171.7 ppm.

Step 2: The diester was dissolved in a 5/1 mixture of 2N HCl and acetic acid (5%) and refluxed for 5-30 hours until TLC showed complete conversion. The reaction was hydrolyzed with satd. NaHCO3 solution and extracted with CH2Cl2. The bound organic layer was dried (Na2SO4), filtered and evaporated to give 5 without further purification. Colorless crystals of 2,6-dimethyl-4-pyrone 0.50 g (1.86 mmol) were obtained (87% yield).

References

[1] Belsky, I. “The reaction of phosgene with 2,6-dimethyl-4H-pyran-4-one.” Tetrahedron 28 4 (1972): Pages 1001-1008.

2,6-Dimethyl-4H-pyran-4-one(1004-36-0)Related Product Information

• Dimethyl ether
• ETHANE
• Dimethyl phthalate
• Dimethyl fumarate
• Dacthal
• Acetone oxime
• Dimethyl carbonate
• Centchroman
• Dimethyl sulfate
• Tetrahydro-4H-pyran-4-one
• N,N-Dimethylformamide
• Poly(dimethylsiloxane)
• Dimethyl sulfoxide
• Dimethyl disulfide
• Repirinast
• Chelidonic acid monohydrate
• ISODEHYDROACETIC ACID
• 4,6-DIMETHYL-2H-PYRAN-2-ONE