| Identification | More | [Name]
Acetylacetaldehyde dimethyl acetal | [CAS]
5436-21-5 | [Synonyms]
1,1-DIMETHOXY-3-BUTANONE
1,1-DIMETHOXY BUTANONE-3
3-KETOBUTYRALDEHYDE-1-DIMETHYLACETAL
3-KETOBUTYRALDEHYDE DIMETHYL ACETAL
3-KETOBUTYRIC ALDEHYDE 1-DIMETHYL ACETAL
3-OXOBUTYRALDEHYDE DIMETHYLACETAL
4,4-DIMETHOXY-2-BUTANONE
4,4-DIMETHOXY BUTAN-2-ONE
4,4-dimethoxybutanon
AADMA
ACETOACETALDEHYDE-1,1-DIMETHYL ACETAL
ACETOACETALDEHYDE DIMETHYL ACETAL
ACETYLACETALDEHYDE DIMETHYL ACETAL
DMB
FADMA
FEMA 3381
FORMYLACETONE DIMETHYL ACETAL
KBA
3-Oxobutyraldehyde 1-(dimethylacetal)
4,4-dimethoxy-2-butanon | [EINECS(EC#)]
226-605-1 | [Molecular Formula]
C6H12O3 | [MDL Number]
MFCD00008789 | [Molecular Weight]
132.16 | [MOL File]
5436-21-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless to yellow liquid | [Melting point ]
-82 °C
| [Boiling point ]
70-73 °C/20 mmHg (lit.) | [density ]
0.996 g/mL at 25 °C(lit.)
| [FEMA ]
3381 | [refractive index ]
n20/D 1.414(lit.)
| [Fp ]
121 °F
| [storage temp. ]
Flammables area | [solubility ]
soluble in Chloroform, Ethyl Acetate | [form ]
Liquid | [color ]
Clear colorless to yellow | [Odor]
at 0.10 % in dipropylene glycol. ethereal musty nutty alcoholic bitter | [Odor Type]
ethereal | [Water Solubility ]
decomposes | [Detection Methods]
GC,NMR | [JECFA Number]
593 | [BRN ]
1702372 | [InChIKey]
PJCCSZUMZMCWSX-UHFFFAOYSA-N | [LogP]
0.33 | [CAS DataBase Reference]
5436-21-5(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Butanone, 4,4-dimethoxy-(5436-21-5) | [EPA Substance Registry System]
5436-21-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F | [Risk Statements ]
R10:Flammable. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 1989 3/PG 3
| [WGK Germany ]
2
| [RTECS ]
EL7592500
| [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29145000 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless to yellow liquid | [Uses]
Acetaldehyde dimethyl acetal is used as a flavoring agent. It is also used in the preparation of (R)-4,4-dimethoxy-2-butanol, pyrazoles and pyrimidines. Further, it is used in the preparation of N,N-diethyl-[2-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]-pyrimidin-3-yl]acetamide and acetoacetaldehyde. | [Definition]
ChEBI: 4,4-Dimethoxy-2-butanone is a ketone. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 41, p. 3765, 1976 DOI: 10.1021/jo00885a028
Tetrahedron Letters, 28, p. 6657, 1987 DOI: 10.1016/S0040-4039(00)96938-7 | [General Description]
4,4-Dimethoxy-2-butanone (Acetylacetaldehyde dimethylacetal) is a ketone. | [Synthesis]
Methanol was added to the 3L and 2L flasks, 257 g of sodium methanolate (1.852 mol) was dissolved in methanol and the temperature was maintained at 40 °C. A mixture of 118.1 g of acetone (2.036 mol) and 333.6 g of methyl formate (5.555 mol) was added dropwise to the reaction system at 40 °C for 4 hours. After the dropwise addition, stirring was continued for 1 h. Subsequent cooling to 20 °C gave 184 g of formalin acetone sodium salt (92% quantitative yield by HPLC using sodium methanol as standard). The resulting formalin acetone sodium salt was transferred to a necked down 3L reactor, methanol was added, and 6.2 g of sulfuric acid (0.063 mol) was added, keeping the temperature at 30 °C. The reaction solution of formylacetone was added to the reaction system simultaneously with 93.8 g of sulfuric acid (0.957 mol) dropwise at 30 °C or lower for 1 hour, during which the pH was maintained between 0-1. After completion of the dropwise addition, the mixture was continued to be stirred at the same temperature for 4 hours and subsequently cooled to 20°C. The pH was adjusted to 7-8 with 20% sodium hydroxide solution, the resulting salt was removed by filtration, and the distillate was collected by distillation to give a final 195.6 g of 4,4-dimethoxy-2-butanone (80.0% yield based on sodium methanol and 87.0% yield based on formalin acetone sodium salt). | [storage]
Store at -20°C | [Toxics Screening Level]
The ITSL for 4,4-dimethoxy-2-butanone is 20 μg/m3 annual average. | [References]
[1] Patent: KR2017/17372, 2017, A. Location in patent: Paragraph 0047; 0065-0070 |
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