6-Amino-2-methylbenzoxazole Chemical Properties

Melting point:

144-146°C

Boiling point:

290.6±13.0 °C(Predicted)

Density 

1.254±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

2.71±0.10(Predicted)

Appearance

Brown to black Solid

InChI

InChI=1S/C8H8N2O/c1-5-10-7-3-2-6(9)4-8(7)11-5/h2-4H,9H2,1H3

InChIKey

NNHTUFOCRUBQCF-UHFFFAOYSA-N

SMILES

O1C2=CC(N)=CC=C2N=C1C

CAS DataBase Reference

5676-60-8(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38-36

Safety Statements 

26-36/37/39

RIDADR 

2811

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2934999090

6-Amino-2-methylbenzoxazole Usage And Synthesis

Chemical Properties

Light brown powder

Synthesis

General procedure for the synthesis of 2-methyl-6-amino benzoxazole from 2-methyl-6-nitrobenzoxazole: To a methanolic (60 mL) suspension of 6-nitro-2-methylbenzoxazole (4.00 g, 22.4 mmol) heated to 70 °C, a water (40 mL) solution of ammonium chloride (12.1 g, 0.227 mol) and iron powder (4.52 g, 80.1 mmol). The reaction mixture was stirred at 70 °C for 2 h. After completion of the reaction, it was filtered through diatomaceous earth and washed with methanol. The filtrate was concentrated and the residue was partitioned between water and ethyl acetate. The organic layers were combined and the solvent was removed under reduced pressure to afford the target product 2-methyl-6-aminobenzoxazole in a yield of 2.83 g (85% yield). The product was analyzed by high performance liquid chromatography (HPLC) with 100% purity (System A); low resolution electrospray ionization mass spectrometry (LRESIMS, ESI+) showed m/z = 149 ([M + H]+).

References

[1] Patent: WO2009/150144, 2009, A1. Location in patent: Page/Page column 137
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 28, p. 5082 - 5088
[3] Journal of the Chemical Society, 1928, p. 121
[4] Journal of the Chemical Society, 1930, p. 2685,2687
[5] DRP/DRBP Org.Chem.,

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