| Identification | More | [Name]
4-Bromo-3,5-dimethylisoxazole | [CAS]
10558-25-5 | [Synonyms]
4-BROMO-3,5-DIMETHYLISOXAZOLE
BUTTPARK 33\06-98
TIMTEC-BB SBB003784
4-BROMO-3,5-DIMETHYLISOXAZOLE 97%
4-Bromo-3,5-dimethylisoxazole, tech. | [EINECS(EC#)]
-0 | [Molecular Formula]
C5H6BrNO | [MDL Number]
MFCD00068187 | [Molecular Weight]
176.01 | [MOL File]
10558-25-5.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to light yellow liquid | [Boiling point ]
176 °C(lit.) | [density ]
1.478 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.486(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep Cold | [form ]
clear liquid | [pka]
-2.35±0.28(Predicted) | [color ]
Colorless to Light orange to Yellow | [Sensitive ]
Light Sensitive | [BRN ]
108522 | [InChI]
InChI=1S/C5H6BrNO/c1-3-5(6)4(2)8-7-3/h1-2H3 | [InChIKey]
GYHZPSUAMYIFQD-UHFFFAOYSA-N | [SMILES]
O1C(C)=C(Br)C(C)=N1 | [CAS DataBase Reference]
10558-25-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [Hazard Note ]
Keep Cold/Light Sensitive | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to light yellow liquid | [Uses]
4-Bromo-3,5-dimethylisoxazole may be used in the preparation of (tert-butyldimethylsilyl)-(3,5-dimethylisoxazol-4-yl)phenylamine and 3,3′,5,5′-tetramethyl-4,4′-diisoxazole.[21} | [General Description]
4-Bromo-3,5-dimethylisoxazole is also known as 3,5-dimethyl-4-bromoisoxazole. | [Synthesis]
The general procedure for the synthesis of 4-bromo-3,5-dimethylisoxazole from 3,5-dimethylisoxazole is as follows:
1. Preparation of intermediate 105 (4-bromo-3,5-dimethyl-1,2-oxazole): DMF (53 mL) was added to a 250 mL round-bottomed flask fitted with a magnetic stirrer.
2. 3,5-dimethyl-1,2-oxazole (5.3 g, 54.57 mmol) and N-iodosuccinimide (11.659 g, 65.49 mmol) were sequentially added to the stirred DMF.
3. After completion of the addition, the reaction mixture was heated to 75°C and maintained for 3 hours.
4. Upon completion of the reaction, the mixture was diluted with ethyl acetate (100 mL).
5. The organic layer was washed sequentially with saturated NaHCO3 solution (100 mL), sodium thiosulfate solution (100 mL), water (200 mL) and brine (100 mL).
6. The organic layer was dried over anhydrous Na2SO4 and then concentrated under reduced pressure to remove the solvent to afford the target product 4-bromo-3,5-dimethyl-1,2-oxazole (6.1 g, 63.4% yield). | [References]
[1] Patent: WO2012/11125, 2012, A1. Location in patent: Page/Page column 148; 149
[2] Rend. Ist. lomb., 1936, vol. 69, p. 587,600 |
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