Acetylacetaldehyde dimethyl acetal Chemical Properties

Melting point:

-82 °C

Boiling point:

70-73 °C/20 mmHg (lit.)

Density 

0.996 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.414(lit.)

FEMA 

3381 | 3-OXOBUTANAL DIMETHYL ACETAL

Flash point:

121 °F

storage temp. 

Inert atmosphere,Room Temperature

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

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

2-Butanone, 4,4-dimethoxy- (5436-21-5)

Safety Information

Hazard Codes 

F

Risk Statements 

10

Safety Statements 

16

RIDADR 

UN 1989 3/PG 3

WGK Germany 

2

RTECS 

EL7592500

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29145000

MSDS

• Language:English Provider:KBA
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Acetylacetaldehyde dimethyl acetal Usage And Synthesis

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.

Uses

4,4-Dimethoxy-2-butanone (β-ketobutyracetal) may be used in the preparation of:

• (R)-4,4-dimethoxy-2-butanol
• pyrazoles and pyrimidines
• [7,16-dihydro- 6,15( 17)-dimetbyldibenzo[b,i]-[1,4,8,11]tetrilazacyclotetradecinato-N⁵,N⁹,N¹⁴,N¹⁸]nickel{II)

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).

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

Acetylacetaldehyde dimethyl acetal(5436-21-5)Related Product Information

• Dimethyl sulfide
• Dimethyl sulfate
• Dimethyl ether
• Dimethyl carbonate
• Dimethyl sulfoxide
• N,N-Dimethylformamide
• Diphenyldimethoxysilane
• Dimethyldimethoxysilane
• 2-Butanone oxime
• 1,1-Dimethoxyethane
• Dimethyl fumarate
• 4-Methyl-2-pentanone
• ETHANE
• Acetal
• Trospectomycin
• 2-Butanone
• Spectinomycin dihydrochloride
• SPECTINOMYCIN SULFATE