5467-70-9

Basic information

• Product Name: 2-AMINO-4'-METHYLACETOPHENONE HYDROCHLORIDE
• Synonyms: 2-AMINO-1-P-TOLYL-ETHANONE HYDROCHLORIDE;2-OXO-2-P-TOLYL-ETHYL-AMMONIUM, CHLORIDE;4-Methylphenacylamine hydrochloride;Nsc25403;Ethanone, 2-amino-1-(4-methylphenyl)-, hydrochloride;2-aMino-1-(4-Methylphenyl)ethan-1-one hydrochloride;2-AMino-4-tolylacetophenonehydrochloride;2-AMino-1-(4-Methylphenyl)-ethanone Hydrochloride
• CAS NO: 5467-70-9
• Molecular Formula: C₉H₁₁NO*ClH
• Molecular Weight: 185.65
• Product Categories: Amines;Aromatics
• Mol File: 5467-70-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 220℃ (dec.)
• Boiling Point: 272.6°Cat760mmHg
• Flash Point: 118.7°C
• Appearance: /
• Density: 1.058g/cm³
• Refractive Index: 1.601
• Storage Temp.: -20°C Freezer
• Solubility: Methanol
• CAS DataBase Reference: 2-AMINO-4'-METHYLACETOPHENONE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4'-METHYLACETOPHENONE HYDROCHLORIDE(5467-70-9)
• EPA Substance Registry System: 2-AMINO-4'-METHYLACETOPHENONE HYDROCHLORIDE(5467-70-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 5467-70-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 5285, 1989 DOI: 10.1016/S0040-4039(01)93765-7

InChI:InChI=1/C12H15N3O/c1-3-15(4-2)11-12(16)14-10-8-6-5-7-9(10)13-11/h5-8H,3-4H2,1-2H3,(H,14,16)

Upstream product

• 6595-30-8 2-azido-1-(4-methylphenyl)ethan-1-one 
• 108-88-3 toluene 
• 4209-24-9 p-methylphenacyl chloride 
• 619-41-0 4-(bromoacetyl)toluene 
• 89204-96-6 5-p-Tolyl-oxazole-4-carboxylic acid methyl ester 
• 18197-26-7 sodium diformamide 
• 93102-92-2 methyl 2-amino-3-oxo-3-p-tolylpropionate hydrochloride 
• 127118-89-2 C₁₁H₁₁NO₃ 
• 62968-73-4 2-nitro-1-(p-tolyl)ethan-1-one 

Downstream Products

• 46985-87-9 5,7,7-trimethyl-2-p-tolyl-7H-thiazolo[3,2-a]pyrimidine 
• 90490-63-4 N-(4-Methylbenzoylmethyl)pyrrole 
• 135103-97-8 N-(trans-2-Iodocyclohexyl)-N'-(p-methylphenacyl)urea 
• 112290-67-2 1,3,4,6-tetra-O-acetyl-2-deoxy-2-<3-(p-methylphenacyl)thioureido>-α-D-glucopyranose 
• 90490-67-8 2-(2,5-Dimethyl-pyrrol-1-yl)-1-p-tolyl-ethanone 
• 53360-85-3 2-amino-1-(4-methylphenyl)ethanol 
• 149403-05-4 (S)-1-(4'-methylphenyl)-2-aminoethanol 
• 97642-98-3 (R)-1-(4'-methylphenyl)-2-aminoethanol 
• 96907-63-0 2,5-bis-(4-methylphenyl)oxazole 
• 96907-70-9 2-(4-Chloro-phenyl)-5-p-tolyl-oxazole 
• 96907-71-0 2-(4-Bromo-phenyl)-5-p-tolyl-oxazole 
• 97814-07-8 1-Benzyl-4-(5-p-tolyl-oxazol-2-yl)-pyridinium; chloride 
• 97814-01-2 Toluene-4-sulfonate1-ethyl-4-(5-p-tolyl-oxazol-2-yl)-pyridinium; 

Relevant articles and documents

Efficient approach to thiazolidinones via a one-pot three-component reaction involving 2-amino-1-phenylethanone hydrochloride, aldehyde and mercaptoacetic acid

A highly efficient three-component reaction has been developed for the synthesis of thiazolidinones involving the reaction of 2-amino-1-phenylethanone hydrochloride with an aromatic aldehyde and mercaptoacetic acid in the presence of diisopropylethylamine in a single pot. Critically, this reaction exhibited excellent chemoselectivity, with the nitrogen atom of the 2-amino-1-phenylethanone component reacting selectively with the aromatic aldehyde to give the corresponding Schiff base. Nucleophilic attack at the carbon of the Schiff base by the sulfur atom of mercaptoacetic, followed by a cyclocondensation reaction between the nitrogen and the carboxylic acid moiety afforded the desired thiazolidinones, which were fully characterized by spectroscopic techniques.

Design, synthesis and evaluation of novel 5-phenylthiophene derivatives as potent fungicidal of Candida albicans and antifungal reagents of fluconazole-resistant fungi

A series of 5-phenylthiophene derivatives with novel structures were designed and synthesized to combat the increasing incidence of susceptible and drug-resistant fungal infections. The antifungal activity of the synthesized compounds was assessed against seven susceptible strains and six fluconazole-resistant strains. It is especially encouraging that compounds 17b and 17f displayed significant antifungal activities against all tested strains. Furthermore, the potent compounds 17b and 17f could prevent the formation of fungi biofilms and 17f displayed satisfactory fungicidal activity. Preliminary mechanistic studies showed that the potent antifungal activity of compound 17f stemmed from inhibition of C. albicans CYP51. In addition, Compounds 17b and 17f were almost nontoxic to mammalian A549, MCF-7, and THLE-2 cells. These results strongly suggested that compounds 17b and 17f are promising as novel antifungal drugs.

Combating fluconazole-resistant fungi with novel β-azole-phenylacetone derivatives

A series of β-azole-phenylacetone derivatives with novel structures were designed and synthesized to combat the increasing incidence of susceptible fungal infections and drug-resistant fungal infections. The antifungal activity of the synthesized compounds was assessed against five susceptible strains and five fluconazole-resistant strains. Antifungal activity tests showed that most of the compounds exhibited excellent antifungal activities against five pathogenic strains with MIC values in the range of 0.03–1 μg/mL. Compounds with R1 = 3-F substituted and 15o and 15ae exhibited moderate antifungal activities against fluconazole-resistant strains 17# and CaR with MIC values in the range of 1–8 μg/mL. Compounds with R1 = H or 2-F (such as 15a, 15o, 15p) displayed moderate to good antifungal activity against fluconazole-resistant strains 632, 901 and 904 with MIC values in the range of 0.125–4 μg/mL. Notably, 15o and 15ae exhibited antifungal activity against five susceptible strains and five fluconazole-resistant strains. Preliminary mechanistic studies showed that the potent antifungal activity of compound 15ae stemmed from inhibition of C. albicans CYP51. Compounds 15o, 15z and 15ae were nearly nontoxic to mammalian A549 cells.