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5-Amino-2-nitrobenzoic acid is an organic compound with the chemical formula C7H6N2O4. It is a yellow powder and is used as a reactant in various chemical reactions and applications.

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  • 13280-60-9 Structure
  • Basic information

    1. Product Name: 5-Amino-2-nitrobenzoic acid
    2. 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+%
    3. CAS NO:13280-60-9
    4. Molecular Formula: C7H6N2O4
    5. Molecular Weight: 182.13
    6. EINECS: 236-283-4
    7. 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
    8. Mol File: 13280-60-9.mol
  • Chemical Properties

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

    1. Hazard Codes: Xn
    2. Statements: 36/37/38-22-20/21/22
    3. Safety Statements: 26-36/37/39-37/39-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 13280-60-9(Hazardous Substances Data)

13280-60-9 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.]

Check Digit Verification of cas no

The CAS Registry Mumber 13280-60-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,2,8 and 0 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 13280-60:
(7*1)+(6*3)+(5*2)+(4*8)+(3*0)+(2*6)+(1*0)=79
79 % 10 = 9
So 13280-60-9 is a valid CAS Registry Number.
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

13280-60-9 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (L16225)  5-Amino-2-nitrobenzoic acid, 95%   

  • 13280-60-9

  • 1g

  • 273.0CNY

  • Detail
  • Alfa Aesar

  • (L16225)  5-Amino-2-nitrobenzoic acid, 95%   

  • 13280-60-9

  • 5g

  • 848.0CNY

  • Detail
  • Alfa Aesar

  • (L16225)  5-Amino-2-nitrobenzoic acid, 95%   

  • 13280-60-9

  • 25g

  • 3272.0CNY

  • Detail
  • Aldrich

  • (564613)  5-Amino-2-nitrobenzoicacid  97%

  • 13280-60-9

  • 564613-5G

  • 1,428.57CNY

  • Detail

13280-60-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Amino-2-nitrobenzoic acid

1.2 Other means of identification

Product number -
Other names Benzoic acid, 5-amino-2-nitro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13280-60-9 SDS

13280-60-9Relevant articles and documents

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

Galunsky, Boris,Lummer, Karsten,Kasche, Volker

, p. 623 - 632 (2000)

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

Karton-Lifshin, Naama,Shabat, Doron

supporting information; scheme or table, p. 386 - 393 (2012/03/22)

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

Sella, Eran,Weinstain, Roy,Erez, Rotem,Burns, Noah Z.,Baran, Phil S.,Shabat, Doron

supporting information; experimental part, p. 6575 - 6577 (2010/10/21)

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

Seila, Eran,Lubelski, Ariel,Klafter, Joseph,Shabat, Doron

supporting information; experimental part, p. 3945 - 3952 (2010/05/15)

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

Perry-Feigenbaum, Rotem,Baran, Phil S.,Shabat, Doron

scheme or table, p. 4825 - 4828 (2010/02/16)

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

Erez, Rotem,Shabat, Doron

scheme or table, p. 2669 - 2672 (2009/02/02)

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

Seko, Shinzo,Miyake, Kunihito,Kavvamura, Norio

, p. 1437 - 1444 (2007/10/03)

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

Costello, Colleen A.,Kreuzman, Adam J.,Zmijewski, Milton J.

, p. 7469 - 7472 (2007/10/03)

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

-

, (2008/06/13)

A brown reactive dye represented by a free acid of the formula, STR1 wherein R is a hydrogen atom or a C1 to C4 alkyl group, X is --SO2 CH2 CH2 Cl, --SO2 CH=CH2, --SO2 CH2 CH2 OSO3 H or --SO2 CH2 CH2 OPO3 H2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1. This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.

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