| Identification | More | [Name]
3,5-Dimethylisoxazole | [CAS]
300-87-8 | [Synonyms]
3,5-DIMETHOXYISOXAZOLE
3,5-DIMETHYLISOOXAZOLE
3,5-DIMETHYLISOXAZOLE
3,5-DISO
AKOS BBS-00006705
DIMETHYLISOXAZOLE(3,5-)
3,5-dimethyl-isoxazol
3,5-Dwumetyloizoksazolu
U 21221
u21221
3,5-DIMETHYLISOXAZOLE, WACKER QUALITY
3,5-Dimethylisoxazole, 98+%
Isoxazole, 3,5-dimethyl-
Dimexazol
Dimexaxol
3,5-Dimethylisoxazole ,97% | [EINECS(EC#)]
206-100-2 | [Molecular Formula]
C5H7NO | [MDL Number]
MFCD08276492 | [Molecular Weight]
97.12 | [MOL File]
300-87-8.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS TO PALE YELLOW LIQUID | [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.)
| [Fp ]
88 °F
| [storage temp. ]
Flammables area | [solubility ]
50.9g/l | [form ]
clear liquid | [pka]
-1.35±0.28(Predicted) | [color ]
Colorless to Light yellow to Light orange | [Specific Gravity]
0.99 | [PH]
4.5 (10g/l, H2O, 20℃) | [Water Solubility ]
insoluble | [Detection Methods]
HPLC | [BRN ]
106324 | [InChI]
1S/C5H7NO/c1-4-3-5(2)7-6-4/h3H,1-2H3 | [InChIKey]
FICAQKBMCKEFDI-UHFFFAOYSA-N | [SMILES]
Cc1cc(C)on1 | [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]
300-87-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R10:Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [RTECS ]
NY2774200
| [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29349990 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Flam. Liq. 3 |
| Hazard Information | Back Directory | [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 |
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