4-Nitrophenethylamine hydrochloride Chemical Properties

Melting point:

200 °C (dec.)(lit.)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol almost transparency.

form 

Crystalline Powder

color 

Yellow to yellow-green

BRN 

3568915

Stability:

Hygroscopic

InChI

InChI=1S/C8H10N2O2.ClH/c9-6-5-7-1-3-8(4-2-7)10(11)12;/h1-4H,5-6,9H2;1H

InChIKey

JVMHULJEYUQYSH-UHFFFAOYSA-N

SMILES

C1([N+]([O-])=O)C=CC(CCN)=CC=1.Cl

CAS DataBase Reference

29968-78-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-40

Safety Statements 

22-24/25-36-26

WGK Germany 

3

HS Code 

29214990

MSDS

• Language:English Provider:2-(4-Nitrophenyl)ethylamine hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

4-Nitrophenethylamine hydrochloride Usage And Synthesis

Chemical Properties

yellow to brown crystalline powder and chunks

Uses

4-Nitrophenethylamine hydrochloride was used in the synthesis of ortho-metalated primary phenethylamines complexes containing six-membered palladacycles and N-(4-nitrophenethyl)formamide.

Preparation

The preparation of 4-Nitrophenethylamine hydrochloride is as follows:Ten mL of 2M HCl was then added in a one-pot fashion, and, in all cases but threonine, the reaction vessel was heated to 190°Cover 5 min with stirring and then allowed to cool. In the case of the temperature-sensitive threonine, soxhlet extraction with toluene was performed at 80°C to remove R-carvone from the reaction mixture. The aqueous reaction mixture was washed three times with 25 mL of ether, and then water solvent was distilled off from the hydrochloride salt. The hydrochloride salt was transferred to a vacuum oven and dried overnight at 150 °C and 10 Torr.

Synthesis

In a reactor, 140 kg of N-(4-nitrophenylethyl)acetamide was dissolved in 190 kg of ethanol with constant stirring until complete dissolution. The pH of the reaction mixture was adjusted to 1 using 2 mol/L hydrochloric acid solution.Subsequently, the reaction mixture was heated to 80°C and maintained at this temperature for 20 hrs. Upon completion of the reaction, the reaction solution was cooled to room temperature to induce precipitation of the solid product. The crude product was purified by recrystallization through methanol, and after filtration and centrifugation, 116 kg of 4-nitrophenylethylamine hydrochloride was obtained, and the purity of the final product was 99.6%. The yield of this synthesis step was 84.7%.

References

[1] Patent: CN107759477, 2018, A. Location in patent: Paragraph 0063

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