3,5-Dimethylisoxazole Chemical Properties

Melting point:

-14℃

Boiling point:

142-144 °C(lit.)

Density 

0.99 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.442(lit.)

Flash point:

88 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

50.9g/l

pka

-1.35±0.28(Predicted)

form 

clear liquid

Specific Gravity

0.99

color 

Colorless to Light yellow to Light orange

PH

4.5 (10g/l, H2O, 20℃)

Water Solubility 

insoluble

BRN 

106324

InChIKey

FICAQKBMCKEFDI-UHFFFAOYSA-N

LogP

1.431 (est)

CAS DataBase Reference

300-87-8(CAS DataBase Reference)

NIST Chemistry Reference

Isoxazole, 3,5-dimethyl-(300-87-8)

EPA Substance Registry System

Isoxazole, 3,5-dimethyl- (300-87-8)

Safety Information

Hazard Codes 

Xn

Risk Statements 

10-20/21/22

Safety Statements 

16-36

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

RTECS 

NY2774200

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29349990

MSDS

• Language:English Provider:3,5-Dimethylisoxazole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,5-Dimethylisoxazole Usage And Synthesis

Chemical Properties

clear colourless to pale yellow liquid

Uses

The optimization of 3,5-dimethylisoxazole derivatives to develop potent inhibitors of the BET (bromodomain and extra terminal domain) bromodomain family with good ligand efficiency. It has hypoglycemic activity.

Application

3,5-dimethylisoxazole is an organic intermediate used in the preparation of 4-(chloromethyl)-3,5-dimethylisoxazole.

Preparation

3,5-Dimethylisozole can be synthesized from acetylacetone and hydroxylamine hydrochloride in one step off ring.

Synthesis

General procedure for the synthesis of 3,5-dimethylisoxazole from acetylacetone: To a solution of hydroxylamine hydrochloride (8.34 g, 0.12 mol) in water (10 ml) was slowly added a solution of 2,4-pentanedione (6) (10.2 g, 0.1 mol) in ethanol (10 ml). The reaction mixture was heated to reflux at set temperature for 3 hrs and subsequently cooled to room temperature and slowly poured into cold water (60 ml). The mixture was extracted using ether (3 x 40 ml). All the organic layers were combined and dried with anhydrous sodium sulfate (Na2SO4) followed by evaporation under reduced pressure to remove the solvent to give a brown oily residue. The residue was purified by reduced pressure distillation to afford 3,5-dimethylisoxazole (5) (8.10 g, 82% yield) as a colorless liquid (boiling point 85-86°C, pressure 150 mmHg). The product was characterized by infrared spectroscopy (IR, thin-film method) and the main absorption peaks were: 3132, 2934, 1611, 1455, 1414, 1258, 1011, 886, 795 cm-1. The data of nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3, 400 MHz) were as follows: δ 5.82 (1H, single peak, H-4), 2.36 (3H, single peak , C=CCH3), 2.23 (3H, single peak, N=CCH3). The nuclear magnetic resonance carbon spectrum (13C NMR, CDCl3) data were as follows: δ 11.3, 12.1, 102.3, 159.9, 169.1.

References

[1] Organic Process Research and Development, 2015, vol. 19, # 9, p. 1274 - 1281
[2] Oriental Journal of Chemistry, 2016, vol. 32, # 1, p. 127 - 135
[3] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 127 - 134
[4] Chemical Communications, 2013, vol. 49, # 81, p. 9329 - 9331
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 4, p. 1026 - 1030

3,5-Dimethylisoxazole(300-87-8)Related Product Information

• Dimethyl sulfoxide
• N,N-Dimethylformamide
• Dimethicone
• 1,3-Dimethylbarbituric acid
• Poly(dimethylsiloxane)
• N,N-Dimethylacetamide
• 3,5-Dimethylisoxazole-4-carboxylic acid ,98%,3,5-DIMETHYLISOXAZOLE-4-CARBOXYLIC ACID,3,5-DIMETHYLISOXAZOLE-4-CARBOXYLIC ACID, PURISS, 98%
• Methyl 5-methylisoxazole-3-carboxylate
• 3,5-Dimethylisoxazole-4-carbonyl chloride ,97%,3,5-Dimethylisoxazole-4-carbonylhloride,3,5-DIMETHYLISOXAZOLE-4-CARBONYL CHLORIDE
• Ethyl 3,5-dimethylisoxazole-4-carboxylate ,97%,3,5-Dimethylisoxazole-4-carboxylic acid ethyl ester
• 5-Methyl-3-phenylisoxazole-4-carboxylic acid
• 3-(CHLOROMETHYL)-5-(3,5-DIMETHYLISOXAZOL-4-YL)-1,2,4-OXADIAZOLE
• 3-(2-Chlorophenyl)-5-methylisoxazole-4-carbonyl chloride
• 4-(CHLOROMETHYL)-3,5-DIMETHYLISOXAZOLE
• ETHYL 3-ETHYL-5-METHYL-4-ISOXAZOLECARBOXYLATE
• 5-Methyl-3-phenylisoxazole-4-carbonyl chloride
• 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid
• 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid