4-Iodo-3,5-dimethylisoxazole

4-Iodo-3,5-dimethylisoxazole Property

Melting point:

51 °C

Boiling point:

239.2±35.0 °C(Predicted)

Density 

1.8763 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-2.30±0.28(Predicted)

color 

Light yellow to Yellow to Orange

Sensitive 

Light Sensitive

InChI

InChI=1S/C5H6INO/c1-3-5(6)4(2)8-7-3/h1-2H3

InChIKey

NMNOXVWRJISEFE-UHFFFAOYSA-N

SMILES

O1C(C)=C(I)C(C)=N1

CAS DataBase Reference

10557-85-4(CAS DataBase Reference)

Safety

Risk Statements 

41

Safety Statements 

24/25-39-26

HazardClass 

LIGHT SENSITIVE

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H330Fatal if inhaled

H335May cause respiratory irritation

H350May cause cancer

H372Causes damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P272Contaminated work clothing should not be allowed out of the workplace.

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

P284Wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P330Rinse mouth.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

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

Uses

3,5-Dimethylisoxazole is a heterocyclic organic compound that can be used to prepare α4β1 and α4β7 antagonists.

Synthesis

General procedure for the synthesis of 3,5-dimethyl-4-iodoisoxazole from 3,5-dimethylisoxazole: 1. Preparation of Intermediate 1 (4-iodo-3,5-dimethylisoxazole): Nitric acid (13 mL) was slowly added dropwise (note the exothermic reaction) to a mixture containing 3,5-dimethylisoxazole (31.3 g, 320 mmol) and iodine (37.3 g, 150 mmol) at room temperature. After dropwise addition, the reaction mixture was continued to be stirred for 1 hour. 2. Post-treatment: The reaction mixture was quenched with a mixture of ice and water followed by extraction with dichloromethane (DCM). The organic phase was separated, washed with sodium thiosulfate (Na2S2O3) solution and dried over anhydrous sodium sulfate (Na2SO4). Finally, the organic phase was concentrated under reduced pressure to afford the target product 3,5-dimethyl-4-iodoisoxazole as a yellow solid (60 g, 83% yield). [APCI MS] m/z: 224 [M+H]+, retention time (Rt) 2.17 min.

References

[1] Tetrahedron Letters, 2010, vol. 51, # 41, p. 5423 - 5425
[2] Patent: WO2011/54846, 2011, A1. Location in patent: Page/Page column 40-41
[3] Patent: US2012/232074, 2012, A1. Location in patent: Page/Page column 17
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 10045 - 10065