2-Methyl-1,3-benzoxazole-6-carboxylic acid Chemical Properties

Melting point:

>230°C (dec.)

Boiling point:

353.5±15.0 °C(Predicted)

Density 

1.380±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly, Heated), Methanol (Slightly, Heated)

form 

Solid

pka

3.68±0.30(Predicted)

color 

Pale Beige

Safety Information

HS Code 

2934999090

2-Methyl-1,3-benzoxazole-6-carboxylic acid Usage And Synthesis

Uses

2-Methyl-1,3-benzoxazole-6-carboxylic Acid is used in the synthesis of orexin 1 receptor antagonists, used in the treatment of obesity. Also used in the synthesis of novel benzoxazole amides as novel enhancers of HIV-1 protease inhibitors.

Synthesis

General procedure for the synthesis of 2-methyl-1,3-benzoxazole-6-carboxylic acid from methyl 2-methylbenzo[d]oxazole-6-carboxylate: To a mixed solution of tetrahydrofuran (THF) (300 mL) and water (H2O) (100 mL) of methyl 2-methyl-1,3-benzoxazole-6-carboxylate (8) (12.2 g, 0.064 mol), lithium hydroxide monohydrate (LiOH-H2O) (5.4 g, 0.128 mol) and the reaction mixture was stirred vigorously at room temperature. After 2 h of reaction, THF was removed by rotary evaporator under reduced pressure.The remaining aqueous phase was acidified with acetic acid (HOAc) to pH ≈ 3 and then extracted several times with dichloromethane (CH2Cl2). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated to give a beige solid product (10.2 g, 90% yield): melting point 245-246 °C (literature value 245-246 °C); thin-layer chromatography (TLC) (silica gel plate, unfolding agent ethyl acetate/methanol (90:10), detected under a UV lamp) showed a single spot with an Rf value of 0.38. Nuclear magnetic resonance hydrogen spectrum (1H NMR) (300 MHz, DMSO-d6): δ 2.66 (s, 3H, NCH3), 7.75 (d, J = 8.3 Hz, 1H, H-5), 7.96 (dd, J = 8.3, 1.4 Hz, 1H, H-4), 8.16 (d, J = 0.7 Hz, 1H, H-7), 13.12 (bs , 1H, OH).

References

[1] Patent: EP1782811, 2007, A1. Location in patent: Page/Page column 60
[2] Patent: EP1669348, 2006, A1. Location in patent: Page/Page column 68
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6661 - 6664
[4] Patent: WO2016/100184, 2016, A1. Location in patent: Paragraph 00323-00324
[5] Patent: US2007/160538, 2007, A1. Location in patent: Page/Page column 19-20

2-Methyl-1,3-benzoxazole-6-carboxylic acid(13452-14-7)Related Product Information

• Thiophanate-methyl
• Methyl acetate
• Methyl salicylate
• Kresoxim-methyl
• Sulfamethoxazole
• Tribenuron methyl
• 2-Phenyl-1-propene
• METSULFURON METHYL
• Benzoxazole
• p-Toluenesulfonic acid
• Methyl
• Methyl bromide
• (-)-2-[METHYLAMINO]-1-PHENYLPROPANE
• BENZO[D]OXAZOLE-6-CARBALDEHYDE
• benzo[d]oxazole-6-carboxylic acid
• METHYL 2-(CHLOROMETHYL)-1,3-BENZOXAZOLE-6-CARBOXYLATE
• 2-Methyl-1,3-benzoxazole-6-carboxylic acid
• Benzoxyazole