OTAVA-BB 1217676

OTAVA-BB 1217676 Property

Melting point:

187-188°

Boiling point:

341.6±42.0 °C(Predicted)

Density 

1.332±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

0.23±0.20(Predicted)

Appearance

Light yellow to yellow Solid

Water Solubility 

Sparingly soluble in water (0.76 g/L at 25°C).

CAS DataBase Reference

120711-81-1

Safety

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

HazardClass 

IRRITANT

HS Code 

2934999090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

OTAVA-BB 1217676 Chemical Properties,Usage,Production

Uses

7-Nitro-3,4-dihydro-2H-1,4-benzooxazine can be used as pain drugs to prevent and treat chronic pain.

Synthesis

The general procedure for the synthesis of 7-nitro-3,4-dihydro-2H-1,4-benzisoxazin-3-one from 7-nitro-2H-1,4-benzisoxazin-3-one was as follows: 7-nitro-4H-benzo[1,4]oxazin-3-one (2.00 g, 10.3 mmol) was dissolved in tetrahydrofuran (THF, 10 mL), and borane-THF complex was added subsequently ( 1.0 M solution of THF, 35 mL). The reaction mixture was heated to reflux for 30 min, then cooled to 0 °C and the reaction was quenched with 1 N hydrochloric acid (20 mL). After continued stirring for 30 min, the reaction solution was concentrated to 1/10 of the original volume. the orange solid product was collected by filtration, washed with water and dried under vacuum to afford 7-nitro-3,4-dihydro-2H-1,4-benzisoxazine (1.66 g, 89% yield). The mass spectrum (electrospray positive ion mode) showed m/z 181.1 ([M+H]+) and the mass spectrum (electrospray negative ion mode) showed m/z 179.2 ([M-H]-).1H NMR (400 MHz, DMSO-d6) data were as follows: δ 7.68 (dd, 1H, J = 8.8, 2.6 Hz), 7.53 (s, 1H), 7.47 (d , 1H, J = 2.6 Hz), 6.63 (d, 1H, J = 9.2 Hz), 4.15 (t, 2H, J = 4.4 Hz), 3.44-3.40 (m, 2H).

References

[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 10, p. 2486 - 2496
[2] Patent: WO2006/66174, 2006, A1. Location in patent: Page/Page column 52-53
[3] Patent: US2010/9975, 2010, A1. Location in patent: Page/Page column 35
[4] Journal of the American Chemical Society, 2014, vol. 136, # 38, p. 13277 - 13282
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830