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ChemicalBook--->CAS DataBase List--->4490-82-8

4490-82-8

4490-82-8 Structure

4490-82-8 Structure
IdentificationBack Directory
[Name]

O-ButylhydroxylaMine Hydrochloride
[CAS]

4490-82-8
[Synonyms]

O-butylhydroxylamine HCl
n-Butoxyamine hydrochloride
n-butyloxyamine hydrochloride
O-ButylhydroxylaMine Hydrochloride
[Molecular Formula]

C4H12ClNO
[MDL Number]

MFCD00487631
[MOL File]

4490-82-8.mol
[Molecular Weight]

125.597
Chemical PropertiesBack Directory
[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 DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
[HS Code ]

2928009090
Spectrum DetailBack Directory
[Spectrum Detail]

O-ButylhydroxylaMine Hydrochloride(4490-82-8)1HNMR
Hazard InformationBack Directory
[Synthesis]

1H-Isoindole-1,3(2H)-dione, 2-butoxy-

51951-28-1

O-ButylhydroxylaMine Hydrochloride

4490-82-8

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
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