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 
• 1252786-61-0 C₁₈H₁₆N₂O₈ 
• 1219600-14-2 (HO)2BC₆H₄CH₂OC(O)NHC₆H₃(NO₂)COOH 
• 51366-39-3 4-acetamido-2-methylnitrobenzene 
• 40101-51-7 3-(1,3-dioxoisoindolin-2-yl)benzoic acid 
• 20632-43-3 3-ureido-benzoic acid 
• 320-98-9 5-fluoro-2-nitrobenzoic acid 

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 
• 89165-27-5 4-nitro-3-carboxytrifluoroacetanilide 
• 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 
• 623575-77-9 5-amino-N-(3-{2-[2-(3-amino-propoxy)-ethoxy]-ethoxy}-propyl)-2-nitro-benzamide 
• 899438-45-0 benzyl 5-(dibenzylamino)-2-nitrobenzoate 
• 50670-83-2 5-acetylamino-2-aminobenzene carboxylic acid 
• 123101-68-8 N-(2-Ethylsulfanyl-4-oxo-4H-benzo[d][1,3]oxazin-6-yl)-acetamide 

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.

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Two-component dendritic chain reactions: experiment and theory

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