4-Bromo-3,5-dimethylisoxazole

4-Bromo-3,5-dimethylisoxazole Property

Boiling point:

176 °C(lit.)

Density 

1.478 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.486(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

pka

-2.35±0.28(Predicted)

form 

clear liquid

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

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Keep Cold/Light Sensitive

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

4-Bromo-3,5-dimethylisoxazole Chemical Properties,Usage,Production

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