Ethoxyamine hydrochloride Chemical Properties

Melting point:

130-133 °C(lit.)

storage temp. 

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

Water Solubility 

Soluble in water

solubility 

DMSO (Sparingly), Methanol (Slightly)

form 

Powder, Crystals or Flakes

color 

Dark gray

PH

pH(50g/l, 25℃) : 2.3～2.7

BRN 

3606639

Stability:

Hygroscopic

InChI

InChI=1S/C2H7NO.ClH/c1-2-4-3;/h2-3H2,1H3;1H

InChIKey

NUXCOKIYARRTDC-UHFFFAOYSA-N

SMILES

C(C)ON.Cl

CAS DataBase Reference

3332-29-4(CAS DataBase Reference)

EPA Substance Registry System

Hydroxylamine, O-ethyl-, hydrochloride (3332-29-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-34-20/21/22

Safety Statements 

26-36-45-36/37/39

RIDADR 

3261

WGK Germany 

3

F 

3-10

HS Code 

29280000

MSDS

• Language:English Provider:O-Ethylhydroxylamine hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Ethoxyamine hydrochloride Usage And Synthesis

Chemical Properties

white adhering crystals or crystalline powder

Uses

O-Ethylhydroxylamine hydrochloride was used in the determination of α-hydroxycarbonyl compounds.

reaction suitability

reagent type: derivatization reagent
reaction type: Alkylations

Synthesis

1. 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 mL of dimethylformamide (DMF) under argon protection. Subsequently, 0.27 mL of ethyl iodide (Aldrich) and 0.5 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) were added sequentially and slowly added dropwise. 2. The reaction mixture was stirred at 60 °C for 2 h and then cooled to room temperature. The reaction was terminated by addition of 2N hydrochloric acid solution. 3. The reaction solution was diluted with 20 mL of ethyl acetate and subsequently dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using ethyl acetate/hexane (1:5) as eluent to give 518 mg of the target compound (yield: 88%). 4. The above compound was dissolved in 5 mL of dichloromethane, and 0.11 mL of methylhydrazine (TCI) was slowly added at 0 °C. The reaction solution was stirred at room temperature for 2 hours and then cooled to 0°C again. 5. The resulting solid was collected by filtration and 1 mL of 4M dioxane hydrochloride solution (Aldrich) was added to the filtrate, which was filtered and dried to give 263 mg solid (yield: 100%). 6. 10 mg of the resulting 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. 7. After the reaction solution was cooled to room temperature, it was acidified by adding 2N hydrochloric acid solution and extracted with 20 mL of ether. The organic phase was dried with magnesium sulfate, filtered and concentrated under reduced pressure. 8. The residue was purified by silica gel column chromatography using ethyl acetate/hexane (1:5) as eluent to afford ethoxyamine hydrochloride SAC-1013 (46 mg, yield: 96%). 1H-NMR (300 MHz, CDCl3) δ 5.91-5.76 (m, 2H), 5.34-5.32 (m, 1H), 5.28-5.25 (m, 1H), 5.14 (m, 1H), 4.24-4.10 (m, 3H), 4.04 (q, J = 20.9 Hz, 2H), 3.64-3.48 (m, 1H ), 2.42-0.60 (m, 38H).

References

[1] Patent: US2014/378399, 2014, A1. Location in patent: Paragraph 0097
[2] Farmaco, Edizione Scientifica, 1987, vol. 42, # 10, p. 697 - 708
[3] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 184 - 194

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