4'-Methoxyacetoacetanilide Chemical Properties

Melting point:

115-118 °C

Boiling point:

346.25°C (rough estimate)

Density 

1.1878 (rough estimate)

vapor pressure 

0.001Pa at 20℃

refractive index 

1.5100 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

11.35±0.46(Predicted)

form 

Powder

color 

White to Blue

Water Solubility 

soluble

LogP

0.85 at 23℃ and pH8.3-8.6

CAS DataBase Reference

5437-98-9(CAS DataBase Reference)

NIST Chemistry Reference

Butanamide, 3-oxo-n-(4-methoxyphenyl)-(5437-98-9)

EPA Substance Registry System

Butanamide, N-(4-methoxyphenyl)-3-oxo- (5437-98-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

26-36/37/39

RTECS 

AK4598010

HS Code 

2924297099

MSDS

• Language:English Provider:4'-Methoxyacetoacetanilide
• Language:English Provider:ACROS

4'-Methoxyacetoacetanilide Usage And Synthesis

Chemical Properties

WHITE TO VERY SLIGHTLY YELLOW POWDER

Uses

N-(4-Methoxyphenyl)-3-oxobutanamide is an intermediate in the synthesis of Tafenoquine-d3 Succinate is the labelled analog of Tatenoquine (T004760), a new 8-aminoquinoline with an improved therapeutic index and safety profile as compared to primaquine (P733500).Tafenoquine has the potential to become a widely used drug in the prevention and treatment of malaria infection and could replace some currently used drugs as resistant strains of Plasmodium species increase.

Synthesis Reference(s)

The Journal of Organic Chemistry, 11, p. 803, 1946 DOI: 10.1021/jo01176a024

Synthesis

GENERAL STEPS: In a 100 mL round-bottomed flask, ethyl acetoacetate (0.03 mol) was added to a stirring solution of p-aminoanisole (0.01 mol) dissolved in 10 mL of PEG-300. The reaction mixture was refluxed at 120 °C for 1.5-2 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature and subsequently extracted with cold ether (3 x 10 mL). The organic phases were combined and purified by column chromatography (eluent: hexane solution of 10-25% ethyl acetate) to afford the target product N-(4-methoxyphenyl)-3-oxobutylamide (3a-p). The structure of the final product was confirmed by methods reported in the literature.

References

[1] Synthetic Communications, 2000, vol. 30, # 20, p. 3709 - 3718
[2] Heterocycles, 2008, vol. 75, # 11, p. 2681 - 2701
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 14, p. 3171 - 3177
[4] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 13, p. 1639 - 1641
[5] Journal of Chemical Sciences, 2014, vol. 126, # 1, p. 187 - 195

4'-Methoxyacetoacetanilide(5437-98-9)Related Product Information

• p-Anisidine
• 2'-Chloroacetoacetanilide
• Acetylacetone
• Acetoacetamide
• p-Acetotoluidide
• m-Anisidine
• Acetanilide
• 2-BENZOYLACETANILIDE
• N-ACETYL-L-TYROSINE ETHYL ESTER
• 4-Aminoveratrole
• 4'-Aminoacetanilide
• 4-(Trifluoromethoxy)aniline
• 4'-Nitroacetanilide
• Acetazolamide
• 2,5-Dimethoxyacetoacetanilide
• N-(4-Methylphenyl)-3-oxobutanamide
• 4'-Chloroacetoacetanilide
• N-(Acetoacetyl)anthranilic acid