4-Iodo-3,5-dimethylisoxazole Chemical Properties

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 Information

Risk Statements 

41

Safety Statements 

24/25-39-26

HazardClass 

LIGHT SENSITIVE

HS Code 

29349990

MSDS

• Language:English Provider:ALFA

4-Iodo-3,5-dimethylisoxazole Usage And Synthesis

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

4-Iodo-3,5-dimethylisoxazole(10557-85-4)Related Product Information

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• ISOXAFLUTOLE
• 3,5-Dimethylisoxazole
• Sulfamethoxazole
• 4-IODOISOXAZOLE
• 4-IODO-3-METHYL-5-PHENYLISOXAZOLE
• 4-IODO-3,5-DIPHENYLISOXAZOLE
• 4-IODO-5-METHYL-3-PHENYLISOXAZOLE
• 4-Iodo-3,5-dimethylisoxazole
• 5-TERT-BUTYL-4-IODO-3-PHENYLISOXAZOLE
• 3-HEXYL-4-IODO-5-PHENYLISOXAZOLE
• 3-(4-IODO-5-PHENYLISOXAZOL-3-YL)-1-METHYLINDOLE
• 5-CYCLOHEX-1-ENYL-4-IODO-3-PHENYLISOXAZOLE
• 3-TERT-BUTYL-4-IODO-5-PHENYLISOXAZOLE