3,5-Dimethyl-4-isoxazolamine Chemical Properties

Melting point:

41-46 °C(lit.)

Boiling point:

78-80°C 0,4mm

Density 

1.118±0.06 g/cm3(Predicted)

storage temp. 

-20°C

pka

1.59±0.10(Predicted)

form 

solid

Appearance

Light yellow to yellow Solid

CAS DataBase Reference

31329-64-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

2934999090

MSDS

• Language:English Provider:SigmaAldrich

3,5-Dimethyl-4-isoxazolamine Usage And Synthesis

Uses

4-Amino-3,5-dimethylisoxazole may be used in the synthesis of 3,5-dimethyl-4-phenylazoisoxazole via reaction with nitrosobenzene.The diazonium salt of 4-Amino-3,5-dimethylisoxazole can react with cupric sulfate to form acetyltriazole derivatives.

General Description

4-Amino-3,5-dimethylisoxazole can be prepared via reduction of 3,5-dimethyl-4-nitroisoxazole in the presence of Zn/NH₄Cl in H₂O.

Synthesis

Step A Synthesis of 3,5-dimethylisoxazol-4-amine: 12.00 g (84.44 mmol) of 3,5-dimethyl-4-nitroisoxazole was dissolved in 430 ml of water and 106.15 g (1.984 mol) of ammonium chloride was added. At 4°C, 46.93 g (7.17 mol) of zinc powder was added in batches over a period of 2 hours. Upon completion of the reaction, ethyl acetate was added to the reaction mixture for extraction and the organic phase was filtered through diatomaceous earth to remove solid impurities. The organic layer was dried with anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure to afford 3,5-dimethylisoxazol-4-amine in 86% (8.10 g) yield. The product was characterized by 1H-NMR (300 MHz, CDCl3): δ= 2.20 (s, 3H) ppm; 2.28 (s, 3H) ppm; 2.51 (wide s, 2H) ppm.

References

[1] Helvetica Chimica Acta, 1991, vol. 74, # 3, p. 531 - 542
[2] Journal of the Chemical Society, 1921, vol. 119, p. 702
[3] Gazzetta Chimica Italiana, 1941, vol. 71, p. 327,336
[4] Patent: US2003/187028, 2003, A1
[5] Patent: US2002/82264, 2002, A1

3,5-Dimethyl-4-isoxazolamine(31329-64-3)Related Product Information

• 3,5-Dimethylisoxazole
• Sulfamethoxazole
• N,N-Dimethylformamide
• Glycine
• Dimethyl phthalate
• Dimethyl sulfide
• Isoxazole
• ISOXAFLUTOLE
• Dimethyl fumarate
• Dimethyl sulfoxide
• Dimethyl ether
• Sulfisoxazole
• ALTRENOGEST
• ETHANE
• N,N-Dimethyl-1,4-phenylenediamine
• Betaine
• 3,5-DIMETHYLISOXAZOL-4-YL ISOCYANATE
• N,N'-BIS(5-METHYL-3-PHENYL-4-ISOXAZOLYL)UREA