(5-Methylisoxazol-3-yl)methanol Chemical Properties

Boiling point:

64°C (0.2 mmHg)

Density 

1.46

storage temp. 

2-8°C

form 

Liquid

pka

13.12±0.10(Predicted)

color 

Colorless

CAS DataBase Reference

35166-33-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36/37/39-26

HazardClass 

IRRITANT

HS Code 

29349990

(5-Methylisoxazol-3-yl)methanol Usage And Synthesis

Chemical Properties

Colorless to light yellow liquid

Uses

3-Hydroxymethyl-5-methylisoxazole (5-Methylisoxazole-3-methanol) is a biochemical reagent that can be used as a biological material or organic compound for life science related research[1].

Synthesis

General procedure for the synthesis of (5-methylisoxazol-3-yl)methanol from methyl 5-methylisoxazole-3-carboxylate: Methyl 5-methylisoxazole-3-carboxylate (14.12 g, 100 mmol) was dissolved in anhydrous THF (150 mL) and cooled to -75 °C in a dry ice/isopropanol bath to form a white suspension. A THF solution of 1 M lithium aluminum hydride (105 mL, 105 mmol) was slowly added, and the rate of addition was controlled to maintain the internal temperature below -55 °C. The reaction mixture gradually turned yellow and was subsequently allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was again cooled to -75 °C, cold water was carefully added until gas release ceased, and then the pH was adjusted to 1-2 with aqueous 6N HCl. The reaction mixture became viscous and was concentrated under reduced pressure to remove the solvent. The residue was dissolved in toluene and azeotropized to remove water. After drying, the residue was washed with chloroform (3 x 100 mL), the chloroform solution was filtered to remove insoluble solids, and finally the solvent was evaporated to give the light yellow oily product (5-methylisoxazol-3-yl)methanol in a yield of 8.34 g (74% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 6.02 (s, 1H), 4.66 (s, 2H), 2.80-3.10 (m, 1H), 2.39 (s, 3H).

References

[1] Bergmeyer H U, et al. Biochemical reagents[M]//Methods of Enzymatic Analysis. Academic Press, 1965: 967-1037.

(5-Methylisoxazol-3-yl)methanol(35166-33-7)Related Product Information

• 5-Methylisoxazole
• ISOXAFLUTOLE
• Isoxazole
• Hydroxypropyl methyl cellulose
• 5-Methylisoxazole-3-carboxylic acid
• Sulfisoxazole
• Sulfamethoxazole
• 4-Methyl-2-pentanol
• Methanol
• ISOFENPHOS-METHYL
• ETHYL 5-METHYLISOXAZOLE-3-CARBOXYLATE
• 5-ETHYL-ISOXAZOLE-3,4-DICARBOXYLIC ACID DIETHYL ESTER
• Methyl 5-methylisoxazole-3-carboxylate
• 5-PHENYLISOXAZOLE-3-CARBOXYLIC ACID
• ETHYL 5-(2-BROMOACETYL)ISOXAZOLE-3-CARBOXYLATE
• Oxazole
• ETHYL 5-TERT-BUTYLISOXAZOLE-3-CARBOXYLATE
• ETHYL 4-[(4-CHLOROANILINO)CARBONYL]-5-METHYL-3-ISOXAZOLECARBOXYLATE