3-Amino-5-tert-butylisoxazole Chemical Properties

Melting point:

110-114 °C

Boiling point:

248.1±28.0 °C(Predicted)

Density 

1.042±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.37±0.10(Predicted)

color 

White to Light yellow

BRN 

1100990

InChI

InChI=1S/C7H12N2O/c1-7(2,3)5-4-6(8)9-10-5/h4H,1-3H3,(H2,8,9)

InChIKey

GGXGVZJHUKEJHO-UHFFFAOYSA-N

SMILES

O1C(C(C)(C)C)=CC(N)=N1

CAS DataBase Reference

55809-36-4(CAS DataBase Reference)

EPA Substance Registry System

3-Isoxazolamine, 5-(1,1-dimethylethyl)- (55809-36-4)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-37/38-36

Safety Statements 

26-36-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2934999090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Amino-5-tert-butylisoxazole Usage And Synthesis

Uses

Amination of aryl bromides catalyzed by Pd(dba)3 (Aldrich Catalog No. 328774) and Xantphos (Aldrich Catalog No. 526460).1

Uses

Amination of aryl bromides catalyzed by Pd(dba)₃ (Aldrich Catalog No. 328774) and Xantphos (Aldrich Catalog No. 526460).

Uses

3-Amino-5-tert-butylisoxazole is a degradation product of herbicide isouron.

Synthesis

Example 1: Gaseous hydrogen chloride (26.3 g) was added to 4,4-dimethyl-3-oxopentanenitrile (75.102 g) suspended in a mixture of anhydrous toluene (150 ml) and anhydrous methanol (26.7 ml) at 5° C. to 10° C. with continuous stirring. Subsequently, the reaction mixture was allowed to stand at 10° to 12°C for 23 hours. Under cooling and stirring conditions, anhydrous methanol (750 ml) followed by triethylamine (185.178 g) was added slowly and dropwise to the reaction mixture until a complete solution was formed. Next, hydroxylamine sulfate (51.704 g) was added and the reaction mixture was stirred at 50°C for 2 hours. After completion of the reaction, the mixture was concentrated. Hydrochloric acid (112.629 g) was added dropwise to the concentrated mixture and stirring was continued at 50 °C for 1 hour. After removal of the solvent by evaporation under reduced pressure, the residue was adjusted to alkaline with 48% aqueous sodium hydroxide solution under cooling conditions, followed by extraction of the aqueous solution with toluene. After the organic layer was washed with water, the solvent was removed by azeotropic distillation at atmospheric pressure and finally dried to give 3-amino-5-tert-butylisoxazole (79.480 g) with a melting point of 106° to 109°C and a yield of 94.5%.

References

[1] Patent: US4200757, 1980, A
[2] Patent: WO2013/100632, 2013, A1. Location in patent: Page/Page column 42; 43
[3] Patent: US2014/371219, 2014, A1. Location in patent: Paragraph 0288; 0289; 0290
[4] Molecules, 2014, vol. 19, # 2, p. 2004 - 2028
[5] Heterocycles, 1991, vol. 32, # 6, p. 1153 - 1158

3-Amino-5-tert-butylisoxazole(55809-36-4)Related Product Information

• tert-Butyl methyl ether
• tert-Butanol
• 4-tert-Butylcatechol
• Glycine
• Methyl 4-tert-butylbenzoate
• tert-Butylchlorodiphenylsilane
• Sulfisoxazole
• 6-Aminocaproic acid
• 3-Aminophenol
• Sulfamethoxazole
• tert-Butyldimethylsilyl chloride
• tert-Butyl hydroperoxide
• tert-Butylhydroquinone
• ALTRENOGEST
• 4-tert-Butylphenol
• ISOXAFLUTOLE
• Isoxazole
• Tris(hydroxymethyl)aminomethane