66108-30-3

Basic information

• Product Name: 2'-HYDROXY-5'-METHYL-3'-NITROACETOPHENONE
• Synonyms: 2'-HYDROXY-5'-METHYL-3'-NITROACETOPHENONE;2-HYDROXY-5-METHYL-3-NITROACETOPHENONE;1-(2-HYDROXY-5-METHYL-3-NITROPHENYL)ETHANONE;LABOTEST-BB LT00452352
• CAS NO: 66108-30-3
• Molecular Formula: C₉H₉NO₄
• Molecular Weight: 195.17
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);C9;Carbonyl Compounds;Ketones
• Mol File: 66108-30-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 133-136 °C(lit.)
• Boiling Point: 254 °C at 760 mmHg
• Flash Point: 106 °C
• Appearance: /
• Density: 1.323 g/cm³
• PKA: 7?+-.0.38(Predicted)
• CAS DataBase Reference: 2'-HYDROXY-5'-METHYL-3'-NITROACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-5'-METHYL-3'-NITROACETOPHENONE(66108-30-3)
• EPA Substance Registry System: 2'-HYDROXY-5'-METHYL-3'-NITROACETOPHENONE(66108-30-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 66108-30-3(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of nitric acid on 2-hydroxy5-methylacetophenone in acetic acid.

Upstream product

• 140-39-6 1-acetoxy-4-methylbenzene 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 

Downstream Products

• 372101-93-4 8-amino-2-(3-amino4-hydroxyphenyl)-3-hydroxy-6-methyl-4H-chromen-4-one 
• 372101-98-9 (E)-3-[4-(benzyloxy)phenyl]-1-(2-hydroxy-5-methyl-3-nitrophenyl)-2-propen-1-one 
• 372102-21-1 (E)-3-[3-(benzyloxy)phenyl]-1-(2-hydroxy-5-methyl-3-nitrophenyl)-2-propen-1-one 
• 372102-17-5 (E)-1-(2-hydroxy-5-methyl-3-nitrophenyl)-3-(4-nitrophenyl)-2-propen-1-one 
• 70977-71-8 3-acetyl-2-hydroxy-5-methylaniline 
• 1355198-82-1 2-hydroxy-5-methyl-3-nitroacetophenone isonicotinoylhydrazone 
• 1441772-90-2 3-hydroxy-6-methyl-8-nitro-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one 

Relevant articles and documents

Contributions of inner and outer coordination sphere bonding in determining the strength of substituted phenolic pyrazoles as copper extractants

Alkyl-substituted phenolic pyrazoles such as 4-methyl-2-[5-(n-octyl)-1H-pyrazol-3-yl]phenol (L2H) are shown to function as Cu-extractants, having similar strength and selectivity over Fe(iii) to 5-nonylsalicylaldoxime which is a component of the commercially used ACORGA solvent extraction reagents. Substitution in the phenol ring of the new extractants has a major effect on their strength, e.g. 2-nitro-4-methyl-6-[5-(2,4,4-trimethylpentyl)-1H-pyrazol-3-yl]phenol (L4H) which has a nitro group ortho to the phenolic hydroxyl group unit and has an extraction distribution coefficient for Cu nearly three orders of magnitude higher than its unsubstituted analogue 4-methyl-6-[5-(2,4,4-trimethylpentyl)-1H-pyrazol-3-yl]phenol (L8H). X-ray structure determinations and density functional theory (DFT) calculations confirm that inter-ligand hydrogen bonding between the pyrazole NH group and the phenolate oxygen atom stabilise the Cu-complexes, giving pseudomacrocyclic structures. Electron-accepting groups ortho to the phenol oxygen atoms buttress the inter-ligand H-bonding, enhancing extractant strength but the effectiveness of this is very dependent on steric factors. The correlation between the calculated energies of formation of copper complexes in the gas phase and the observed strength of comparably substituted reagents in solvent extraction experiments is remarkable. Analysis of the energies of formation suggests that big differences in strength of extractants arise principally from a combination of the effects of the substituents on the ease of deprotonation of the proligands and, for the ortho-substituted ligands, their propensity to buttress inter-ligand hydrogen bonding.

Nitration of acetophenone, chalcone, flavanone and flavone with copper nitrate-acetic anhydride

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