2-Aminoacetophenone hydrochloride Chemical Properties

Melting point:

194 °C (dec.)(lit.)

storage temp. 

Refrigerator (+4°C)

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Crystals

color 

Slightly yellow to beige

BRN 

3563173

Stability:

Hygroscopic

InChI

InChI=1S/C8H9NO.ClH/c9-6-8(10)7-4-2-1-3-5-7;/h1-5H,6,9H2;1H

InChIKey

CVXGFPPAIUELDV-UHFFFAOYSA-N

SMILES

C(C1=CC=CC=C1)(=O)CN.[H]Cl

CAS DataBase Reference

5468-37-1(CAS DataBase Reference)

EPA Substance Registry System

Ethanone, 2-amino-1-phenyl-, hydrochloride (5468-37-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-24/25

WGK Germany 

3

RTECS 

AM5940000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29223990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-Aminoacetophenone hydrochloride Usage And Synthesis

Chemical Properties

Off-white crystalline

Uses

Mixed Salt of α-Aminoacetophenone, used in the preparation og pseudopeptidic inhibitors of human sirtuins1-3. This action effectually displays antiproliferative protperties in cancer cells. Also used in the preparation of dual δ/μopiod receptor agonists.

Synthesis

To a stirred solution of phenacyl bromide (1 mmol, 1 equiv) in diethyl ether (13 mL) was added hexamethylenetetramine (1 mmol, 1 equiv) all at once and the mixture was stirred for 12 h at room temperature. The resulting solid was filtered, washed with diethyl ether (15 mL), and dried under reduced pressure to afford the quaternary salt, which was next placed in a two-necked round-bottomed flask fitted with a reflux condenser, and EtOH (22 mL) was added to it. Concentrated HCl (0.6 mL) was added, and the mixture was refluxed for 3 h (solid formed). After cooling to room temperature, the solid was filtered, washed with EtOH (20 mL), and dried under vacuum to afford pure 2-Aminoacetophenone hydrochloride.

Purification Methods

Crystallise the salt from Me2CO /EtOH, EtOH/ Et2O, 2-propanol or 2-propanol and a little HCl (slowly after a fe

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