O-ButylhydroxylaMine Hydrochloride

O-ButylhydroxylaMine Hydrochloride Property

Melting point:

157.0 to 161.0 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

Safety

HS Code 

2928009090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

O-ButylhydroxylaMine Hydrochloride Chemical Properties,Usage,Production

Synthesis

1. 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 mL of dimethylformamide (DMF) under argon protection. 2. 0.38 mL of 1-iodobutane (Aldrich) and 0.5 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, Aldrich) were added sequentially and slowly. 3. The reaction mixture was stirred at 60 °C for 2 h and subsequently cooled to room temperature. 4. The reaction was terminated by addition of 2 N hydrochloric acid solution and the reaction solution was diluted with 20 mL of ethyl acetate. 5. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. 6. The residue was purified by silica gel column chromatography using ethyl acetate/hexane (1:5) as eluent to give 635 mg of the target compound (95% yield). 7. The above compound was dissolved in 5 mL of dichloromethane and 0.12 mL of methylhydrazine (TCI) was added slowly at 0 °C. 8. The reaction solution was stirred at room temperature for 2 hours and then cooled to 0°C again. 9. The resulting solid was collected by filtration and 1 mL of 4 M dioxane hydrochloride solution (Aldrich) was added to the filtrate, which was filtered and dried to give 257 mg solid (100% yield). 10. 13 mg of the above solid was dissolved with 44 mg of SAC-0906 in 1 mL of pyridine (Aldrich) under argon protection and stirred at 80 °C for 4 hours. 11. The reaction solution was cooled to room temperature, acidified with 2 N hydrochloric acid solution and extracted with 20 mL of ether. 12. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. 13. The residue was purified by silica gel column chromatography using ethyl acetate/hexane (1:5) as eluent to afford O-butylhydroxylamine hydrochloride SAC-1015 (44 mg, 88% yield). 14. The product was characterized by 1H-NMR (300 MHz, CDCl3): δ 5.91-5.76 (m, 2H), 5.34-5.33 (m, 1H), 5.28-5.25 (m, 1H), 5.15 (m, 1H), 4.25-4.10 (m, 3H), 4.02-3.97 (m, 2H), 3.59-3.48 (m, 1H), 3.59-3.48 (m, 2H). (m, 1H), 2.42-0.60 (m, 42H).

References

[1] Patent: US2014/378399, 2014, A1. Location in patent: Paragraph 0100
[2] Farmaco, Edizione Scientifica, 1987, vol. 42, # 10, p. 697 - 708
[3] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 184 - 194
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 7, p. 1844 - 1848