13280-60-9

Basic information

• Product Name: 5-Amino-2-nitrobenzoic acid
• Synonyms: TIMTEC-BB SBB008583;5-AMINO-2-NITROBENZOIC ACID;3-AMINO-6-NITROBENZOIC ACID;3-CARBOXY-4-NITROANILINE;ANBA;2-NITRO-5-AMINOBENZOIC ACID;Benzoic acid, 5-amino-2-nitro-;5-AMINO-2-NITROBENZOIC ACID (PURIFIED)[FOR GAMMA-GT] 99+%
• CAS NO: 13280-60-9
• Molecular Formula: C₇H₆N₂O₄
• Molecular Weight: 182.13
• EINECS: 236-283-4
• Product Categories: FINE Chemical & INTERMEDIATES;Amino Acids and Derivatives;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Aromatics Compounds;Aromatics;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 13280-60-9.mol

Chemical Properties

• Melting Point: 236-238 °C(lit.)
• Boiling Point: 481.3 °C at 760 mmHg
• Flash Point: 244.9 °C
• Appearance: Yellow powder
• Density: 1.568 g/cm³
• Vapor Pressure: 4.5E-10mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO, Methanol
• PKA: 2.28±0.25(Predicted)
• Water Solubility: Insoluble
• BRN: 2107512
• CAS DataBase Reference: 5-Amino-2-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-2-nitrobenzoic acid(13280-60-9)
• EPA Substance Registry System: 5-Amino-2-nitrobenzoic acid(13280-60-9)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22-20/21/22
• Safety Statements: 26-36/37/39-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 13280-60-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
5-Amino-2-nitrobenzoic acid is used as a reactant for two-component dendritic chain reactions, which are important in the synthesis of complex organic molecules and materials.
Used in Enzymic Activation:
5-Amino-2-nitrobenzoic acid is used as an enzymic activator for hydrophobic self-immolative dendrimers. This application allows for the controlled release of active agents in various chemical and biological processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Amino-2-nitrobenzoic acid is used in the preparation of insulin receptor tyrosine kinase activators. These activators play a crucial role in the regulation of glucose metabolism and have potential applications in the treatment of diabetes.
Used in Polymer Chemistry:
5-Amino-2-nitrobenzoic acid is used in the preparation of polymer-bound diazonium salts using Merrifield resin-bound piperazine. This application is important in the synthesis of functional polymers and materials with specific properties and applications.
Overall, 5-Amino-2-nitrobenzoic acid is a versatile compound with various applications in chemical synthesis, enzymic activation, pharmaceutical industry, and polymer chemistry. Its unique chemical properties and reactivity make it a valuable component in the development of new materials and therapeutic agents.

Purification Methods

Crystallise the acid from water. [Beilstein 14 III 1021.]

InChI:InChI=1/C7H6N2O4/c8-4-1-2-6(9(12)13)5(3-4)7(10)11/h1-3H,8H2,(H,10,11)/p-1

Upstream product

• 4368-83-6 2-nitro-5-acetylaminobenzoic acid 
• 552-16-9 ortho-nitrobenzoic acid 
• 7732-18-5 water 
• 52033-70-2 2-nitro-5-[(phenylacetyl)amino]benzoic acid 
• 1055310-21-8 C₃₁H₂₆N₄O₉ 
• 1055310-22-9 C₃₁H₂₆N₄O₉ 
• 1055310-23-0 C₃₉H₃₂N₆O₁₃ 
• 1055310-24-1 C₃₉H₃₂N₆O₁₃ 
• 1204311-34-1 C₃₆H₃₅N₅O₁₁ 
• 1204311-38-5 C₄₄H₄₀N₈O₁₇ 
• 1204311-45-4 C₄₅H₄₁N₇O₁₇ 
• 1204311-29-4 C₃₅H₃₄N₆O₁₁ 
• 1252786-61-0 C₁₈H₁₆N₂O₈ 
• 1219600-14-2 (HO)2BC₆H₄CH₂OC(O)NHC₆H₃(NO₂)COOH 

Downstream Products

• 16994-15-3 ethyl 5-amino-2-nitrobenzoate 
• 552-16-9 ortho-nitrobenzoic acid 
• 610-37-7 5-hydroxy-2-nitrobenzoic acid 
• 610-74-2 1,4-phenylenediamine-2-carboxylic acid 
• 96461-32-4 5-(4-hydroxy-phenylazo)-2-nitro-benzoic acid 
• 62876-66-8 5-dimethylamino-2-nitrobenzoic acid 
• 73651-75-9 4'-nitro-4-dimethylaminoazobenzene-3'-carboxylic acid 
• 201666-47-9 (5-amino-2-nitro-phenyl)-imidazol-1-yl-methanone 
• 623575-76-8 5-amino-N-(8-amino-3,6-dioxaoctyl)-2-nitrobenzamide 
• 77376-03-5 (5-amino-2-nitro-phenyl)-methanol 
• 899438-45-0 benzyl 5-(dibenzylamino)-2-nitrobenzoate 
• 67123-61-9 12-(4'-nitro-4-dimethylaminoazobenzene-3'-carboxyloxy)stearic acid 
• 106-50-3 1,4-phenylenediamine 
• 1055310-30-9 C₁₂H₁₈N₂O₄Si 

Relevant articles and documents

Comparative study of substrate- and stereospecificity of penicillin G amidases from different sources and hybrid isoenzymes

Four natural pencillin G amidase variants from different sources and two genetically constructed hybrid enzymes were produced and purified to homogeneity. The specificity constants of one enzyme (E. coli) were found to differ six orders of magnitude for hydrolytic transformations within a wide range of substrates. The substrate specificity of the homologous penicillin amidases was found to differ less than one order of magnitude for hydrolysis of the most specific and up to two orders of magnitude for the less specific substrates. The S′1-substrate specificity in hydrolytic and transfer reactions (studied mainly with the E. coli enzyme) varied more than three orders of magnitude for the different substrates. The penicillin amidases were found to be R-specific in the S1-binding site and S-specific in the S′1-binding site. The S1-stereoselectivity differs less than one order of magnitude for the different variants. The S′1-stereoselectivity is more pronounced, increases with nucleophile specificity, and was found to differ up to three orders of magnitude in transfer reactions for the enzyme from E. coli. The observed variation of enatioselectivity for different penicillin amidases and one substrate can also be achieved by changes in temperature. Comparison of substrate-and stereospecificity of penicillin amidases from different sources and hybrid isoenzymes suggests that similar changes can be expected for enzyme variants derived by rational protein design or directed evolution.

Exponential diagnostic signal amplification via dendritic chain reaction: The dendritic effect of a self-immolative amplifier component

Signal amplification techniques are commonly used to boost diagnostic signals. We have recently developed a new approach for exponential signal amplification obtained through a distinctive dendritic chain reaction. Here we report evaluation of the effect of the self-immolative dendritic amplifier component on the signal amplification. Four dendrons with various numbers of end-units were evaluated for the ability to produce exponential signal amplification through self-immolative disassembly pathways. The dendron composed of a first-generation platform with three end-units exhibited the best characteristics with rapid disassembly rate and good stability under aqueous conditions. This study demonstrates the efficiency of molecules based on dendritic structures.

Sulfhydryl-based dendritic chain reaction

A new dendritic chain reaction probe system was demonstrated to produce exponential signal amplification for the detection of sulfhydryl compounds.

Two-component dendritic chain reactions: experiment and theory

New analytical diagnostic techniques that are based on signal-amplification mechanisms could significantly improve the sensitivity of detection of various analytes. We have developed a new approach to achieving exponential amplification of a diagnostic signal through a two-component dendritic chain reaction. The chain reaction generated the analyte of interest and thereby initiated additional diagnostic cycles. The system was designed for the detection of hydrogen peroxide and produced significantly larger intensity of diagnostic signal than a classic probe. In addition, a mathematical model that simulates the disassembly kinetics of one-component and two-component reactions was developed and shown to correlate well with the observed experimental data. The modularity and flexibility of a two-component detection system should allow extension to the detection of other analytes.

The pyridinone-methide elimination

The quinone-methide elimination is a common, efficient methodology used in linkers designed to undergo self-fragmentation. Here, for the first time, we demonstrate this elimination in a pyridine ring system. Under physiological conditions, a compound cons

The azaquinone-methide elimination: Comparison study of 1,6- and 1,4-eliminations under physiological conditions

The azaquinone-methide elimination is a powerful and efficient reaction useful for disassembly of spacers in prodrug systems. We and others have used the spacer-technique to develop dendritic and polymeric self-immolative molecular systems that can disass

A convenient copper-catalyzed direct animation of nitroarenes with 9-alkylhydroxylamines

O-Alkylhydroxylamines, particularly O-methylhydroxylamine, aminate nitroarenes in the presence of a strong base and a copper catalyst to give aminonitroarenes in good yields, ortho- or para-Animation with respect to the nitro group takes place, and in some cases the ortho-aminated product is preferentially obtained. With 3-substituted nitrobenzenes where the substituent has a lone pair of electrons, preferential amination occurs at the 2-position to give the sterically most congested 3c-f, 14 and 22g.

Selective deprotection of phthalyl protected amines

Phthalyl amidase selectively deprotects phthalimido groups under very mild aqueous conditions in a one-pot reaction to produce phthalic acid and the free amine. The enzyme has been shown to deprotect several primary amines of distinctly different structure, and exhibits chiral selectivity when the substrate contains extensive β-branching. The enzyme has a definite requirement for ortho positioning of the functional groups on a fixed axis of rotation.

Bisazo brown reactive dye

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