89586-14-1

Basic information

• Product Name: Benzoic acid, 2-(acetyloxy)-4-methyl-3-nitro-, methyl ester
• CAS NO: 89586-14-1
• Molecular Formula: C11H11NO6
• Molecular Weight: 253.211
• Mol File: 89586-14-1.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2-(acetyloxy)-4-methyl-3-nitro-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-(acetyloxy)-4-methyl-3-nitro-, methyl ester(89586-14-1)
• EPA Substance Registry System: Benzoic acid, 2-(acetyloxy)-4-methyl-3-nitro-, methyl ester(89586-14-1)

Safety Data

• Hazardous Substances Data: 89586-14-1(Hazardous Substances Data)

Upstream product

• 51731-17-0 trans-4-methoxy-3-buten-2-one 
• 108-24-7 acetic anhydride 
• 87730-77-6 methyl 4-nitro-3-oxobutyrate 
• 42731-40-8 3-oxo-butyraldehyde; sodium (Z)-1-enolate 

Downstream Products

• 24279-14-9 methyl 6-methyl-3-nitrosalicylate 

Relevant articles and documents

255. Construction of Highly Substituted Nitroaromatic Systems by Cyclocondensation. Part II. Conversion of 4-Nitr-3-oxobutyrate to 3-Nitrosalicylates

The base-catalyzed reaction of 4-nitro-3-oxobutyrate (6) with acetylacetone (8), formylacetone (13), formylcyclohexanone (31), 2,4-dioxopentanoates 39 and 40, and 2,4,6-heptanetrione (2) affords substituted 3-nitrosalicylates, products of a double aldol condensation.With unsymmetrical dicarbonyl compounds both regioisomers are formed.High selectivity was found in the case of β-keto-aldehydes 13 and 31 with preferred addition of the NO2-substituted carbon to the aldehyde carbonyl.The major products of these cyclocondensations, which are isolated in yields ranging from 20 percent to 80 percent, are all new compounds.Less successful are the conversions with β-alkoxy- and β-chloro-vinyl ketones (23, 25, and 26), and with alkinone 24, where the condensation products are formed in very low yield.