2-amino-5-nitrobenzyl alcohol

2-amino-5-nitrobenzyl alcohol Property

Boiling point:

427.3±30.0 °C(Predicted)

Density 

1.432±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

13.67±0.10(Predicted)

Appearance

Light brown to green Solid

Safety

HS Code 

2922190090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H372Causes damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P501Dispose of contents/container to..…

2-amino-5-nitrobenzyl alcohol Chemical Properties,Usage,Production

Uses

(2-Amino-5-nitrophenyl)methanol is used in preparation of Spiropyridooxazinepyrrolidine compounds as dual inhibitors of factor XIa and plasma kallikrein.

Synthesis

General procedure for the synthesis of (2-amino-5-nitrophenyl)methanol from 2-amino-5-nitrobenzoic acid: firstly, compound 24a was prepared from compound 23b according to the literature methodology. after completion of the reaction, the target product 29b was obtained by conventional post-treatment in 92% yield and the product was a butter-like solid. The product was identified by infrared spectroscopy (IR) and the main absorption peaks were located at 3365, 2918, 1612, 1528, 1345, 1239, 1051, 755 cm-1. Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 400 MHz, CDCl3) showed δ : 1.27-1.35 (1H, m), 2.11 (1H, dt, J = 5.3, 12.8 Hz), 2.25 (1H, dt, J = 2.8, 12.0 Hz), 2.36-2.48 (1H, m), 2.43 (3H, s), 2.90-3.00 (2H, m), 2.96 (1H, d, J = 18.0 Hz), 3.10 (1H, d, J = 18.0 Hz), 3.27 (1H, d, J = 7.61 (1H, dd, J = 2.0, 9.6 Hz), 7.67 (1H, s), 8.29 (1H, d, J = 2.0 Hz), two protons (OH) were not observed. The nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, CDCl3) showed δ: 23.9, 35.8, 36.1, 39.1, 40.4, 42.9, 45.3, 61.4, 69.2, 112.6, 115.0, 121.7, 123.3, 125.6, 127.0, 128.3, 129.2, 131.0, 137.2, 140.3, 144.4, 147.0, 155.2, 162.0. High-resolution mass spectrometry (HRMS, ESI) analysis showed calculated value of C24H24N3O4 [M + H]+: 418.1767, measured value: 418.1748.

References

[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Patent: US2014/121415, 2014, A1. Location in patent: Paragraph 0050
[3] Patent: US2010/63037, 2010, A1. Location in patent: Page/Page column 20
[4] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7033 - 7036
[5] Patent: WO2015/164308, 2015, A1