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5-Nitrosalicylic acid, also known as 2-Hydroxy-5-nitrobenzoic acid, is a salicylic acid derivative characterized by a monohydroxybenzoic acid structure with a hydroxy group ortho to the carboxylic acid group and a nitro substituent para to the phenolic hydroxy group. It exhibits an anti-inflammatory effect against colitis and inhibits the activity of wild type-bovine low Mr protein tyrosine phosphatase. This yellow powder is a promising compound for various applications in different industries.

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  • 96-97-9 Structure
  • Basic information

    1. Product Name: 5-Nitrosalicylic acid
    2. Synonyms: 2-hydroxy-5-nitro-benzoicaci;AURORA KA-2534;ANILOTIC ACID;2-HYDROXY-5-NITROBENZOIC ACID;5-NITROSALICYLIC ACID;5-NITRO-2-HYDROXY-BENZOIC ACID;RARECHEM AL BE 0192;TIMTEC-BB SBB006535
    3. CAS NO:96-97-9
    4. Molecular Formula: C7H5NO5
    5. Molecular Weight: 183.12
    6. EINECS: 202-548-8
    7. Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;API intermediates;Carboxylic Acids;Phenyls & Phenyl-Het;C7;Carbonyl Compounds
    8. Mol File: 96-97-9.mol
    9. Article Data: 48
  • Chemical Properties

    1. Melting Point: 228-230 °C(lit.)
    2. Boiling Point: 316.77°C (rough estimate)
    3. Flash Point: 183.9 °C
    4. Appearance: Clear yellow-beige to orange-brown/Liquid
    5. Density: 1,65 g/cm3
    6. Vapor Pressure: 4.36E-07mmHg at 25°C
    7. Refractive Index: 1.6280 (estimate)
    8. Storage Temp.: Storage temperature: no restrictions.
    9. Solubility: water: soluble1g in 1475ml(lit.)
    10. PKA: pK1:2.12 (25°C)
    11. Water Solubility: Soluble in water 1g/1475ml .
    12. Merck: 14,6631
    13. BRN: 2213719
    14. CAS DataBase Reference: 5-Nitrosalicylic acid(CAS DataBase Reference)
    15. NIST Chemistry Reference: 5-Nitrosalicylic acid(96-97-9)
    16. EPA Substance Registry System: 5-Nitrosalicylic acid(96-97-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36-37/39
    4. WGK Germany: 3
    5. RTECS:
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 96-97-9(Hazardous Substances Data)

96-97-9 Usage

Uses

Used in Pharmaceutical Industry:
5-Nitrosalicylic acid is used as an anti-inflammatory agent for its effect against colitis. It helps in reducing inflammation and alleviating symptoms associated with this condition.
Used in Biochemical Research:
5-Nitrosalicylic acid is used as an inhibitor of wild type-bovine low Mr protein tyrosine phosphatase, allowing researchers to study the enzyme's activity and its role in various biological processes.
Used in Chemical Synthesis:
As a salicylic acid derivative, 5-Nitrosalicylic acid can be used as a starting material or intermediate in the synthesis of other related compounds with potential applications in various fields, such as pharmaceuticals, agrochemicals, or dyes.
Used in Analytical Chemistry:
The yellow powder form of 5-Nitrosalicylic acid can be utilized in analytical techniques for the detection, quantification, or identification of specific compounds or elements, taking advantage of its chemical properties.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 2377, 1995 DOI: 10.1016/0040-4039(95)00281-G

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise the acid from Me2CO (charcoal), then twice more from Me2CO alone, aqueous EtOH (m 234-236o) or H2O (m 232-233o). [Beilstein 10 III 197, 10 IV 255.]

Check Digit Verification of cas no

The CAS Registry Mumber 96-97-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 96-97:
(4*9)+(3*6)+(2*9)+(1*7)=79
79 % 10 = 9
So 96-97-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NO5/c9-6-2-1-4(8(12)13)3-5(6)7(10)11/h1-3,9H,(H,10,11)/p-2

96-97-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-nitrosalicylic acid

1.2 Other means of identification

Product number -
Other names Benzoic acid, 2-hydroxy-5-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:96-97-9 SDS

96-97-9Relevant articles and documents

Advanced Real-Time Process Analytics for Multistep Synthesis in Continuous Flow**

Sagmeister, Peter,Lebl, René,Castillo, Ismael,Rehrl, Jakob,Kruisz, Julia,Sipek, Martin,Horn, Martin,Sacher, Stephan,Cantillo, David,Williams, Jason D.,Kappe, C. Oliver

supporting information, p. 8139 - 8148 (2021/03/01)

In multistep continuous flow chemistry, studying complex reaction mixtures in real time is a significant challenge, but provides an opportunity to enhance reaction understanding and control. We report the integration of four complementary process analytical technology tools (NMR, UV/Vis, IR and UHPLC) in the multistep synthesis of an active pharmaceutical ingredient, mesalazine. This synthetic route exploits flow processing for nitration, high temperature hydrolysis and hydrogenation reactions, as well as three inline separations. Advanced data analysis models were developed (indirect hard modeling, deep learning and partial least squares regression), to quantify the desired products, intermediates and impurities in real time, at multiple points along the synthetic pathway. The capabilities of the system have been demonstrated by operating both steady state and dynamic experiments and represents a significant step forward in data-driven continuous flow synthesis.

Method for synthesizing mesalazine

-

, (2020/08/25)

A method for synthesizing mesalazine is disclosed. The method comprises the following steps: 1) adding p-nitrophenol, p-toluenesulfonic acid, absolute ethyl alcohol and hexamethylenetetramine, stopping heating after the reaction is finished, heating to room temperature while stirring with ice water, separating out solids, filtering, washing and drying to obtain 5-nitrosalicylaldehyde; 2) adding the 5-nitrosalicylaldehyde, potassium tert-butoxide, copper salt and acetonitrile, adding tert-butyl hydroperoxide while stirring, after the reaction is finished, performing vacuum concentration to remove the solvent, pouring cold water into residues, stirring, performing suction filtration, adjusting the pH value of the filtrate with hydrochloric acid, performing suction filtration, and drying to obtain 5-nitrosalicylic acid; and 3) adding stannous chloride dihydrate, concentrated hydrochloric acid, the 5-nitrosalicylic acid and ethanol, carrying out vacuum concentration after the reaction is finished, dissolving residues in water, adjusting the pH value with a concentrated hydrochloric acid solution, standing for crystallization, carrying out suction filtration, washing filter cake with water, and drying to obtain mesalazine. No isomer is generated, and the yield is high; the method does not need high-temperature and high-pressure conditions; the reaction cost is low; and raw materialsand auxiliary materials with high toxicity and heavy environmental pollution are not used.

Catalytic oxidation of alcohols and alkyl benzenes to carbonyls using Fe3O4?SiO2?(TEMPO)-: Co -(Chlorophyll-CoIII) as a bi-functional, self-co-oxidant nanocatalyst

Hamah-Ameen, Baram Ahmed,Kazemnejadi, Milad,Mahmoudi, Boshra,Rostami, Amin

, p. 6600 - 6613 (2020/11/16)

Chlorophyll b was extracted from heliotropium europaeum plant, demetalated, allylated and grafted to acrylated TEMPO through a copolymerization protocol. Then, the chlorophyll monomers were coordinated to Co ions, immobilized on magnetic nanoparticles and the resulting hybrid was used as a powerful catalyst for a variety of oxidation reactions. By using the present method, oxidation of benzylic alcohols and alkyl benzenes to carbonyls was accomplished in water under aerobic conditions. Moreover, direct oxidation of alcohols to carboxylic acids was performed by adding NaOCl to the mixture. All entries were oxidized to the corresponding desired product with high to excellent yields and up to 97% selectivity. The catalyst was thoroughly characterized by CV, TGA, VSM, XRD, XPS, DLS, FE-SEM, TEM, UV-Vis, EDX, and BET analyses. The activity of the catalyst was investigated by applying various components of the catalyst to the oxidation model separately. The reasonable mechanisms are suggested based on the cooperation between the TEMPO groups and cobalt(iii) (or Co(iv)) sites on the catalyst. The catalyst could be recovered and reused for at least 7 consecutive recycles without any considerable reactivity loss. This journal is

3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Chaudhary, Renu,Natarajan, Palani,Rani, Neetu,Sakshi,Venugopalan, Paloth

supporting information, (2019/12/30)

Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.

Fe3O4@SiO2@Im[Cl]Mn(III)-complex as a highly efficient magnetically recoverable nanocatalyst for selective oxidation of alcohol to imine and oxime

Kazemnejadi, Milad,Alavi, Seyyedeh Ameneh,Rezazadeh, Zinat,Nasseri, Mohammad Ali,Allahresani, Ali,Esmaeilpour, Mohsen

, p. 230 - 249 (2019/03/28)

An efficient and environmentally friendly oxidation process for the one-pot preparation of oxime, imine and carbonyl compounds through alcohol oxidation in the presence of H2O2 and/or O2 have been developed by a melamine-Mn(III) Schiff base complex supported on Fe3O4@SiO2–Cl nanoparticles, named as Fe3O4@SiO2@Im[Cl]Mn(III)-complex nanocomposite, at room temperature. Direct oxidation of alcohol to carboxylic acid was performed using the catalyst in the presence of molecular O2 at room temperature in a different approach. The oxidation products were obtained with excellent yields and high TOFs. The properties of the catalyst were characterized by Fourier transform infrared spectroscopy (FTIR), elemental analysis (C, H, N), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), dynamic light scattering (DLS), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), inductive coupled plasma (ICP), cyclic voltammetry (CV), nuclear magnetic resonance (1H & 13C NMR), vibration sample magnetometer (VSM), Brunauer– Emmett–Teller (BET) and differential pulse voltammetry (DPV) analyses. The mechanism of the oxidation processes was investigated for the both H2O2 and O2 oxidants. The role of the imidazolium moiety in the catalyst as a secondary functionality was investigated. Chemoselectivity behavior of the catalyst was studied by some combinations. The catalyst could be recycled from the reaction mixture by a simple external magnet and reused for several times without any considerable reactivity loss.

Cathepsin B inhibitors: Further exploration of the nitroxoline core

Sosi?, Izidor,Mitrovi?, Ana,?uri?, Hrvoje,Knez, Damijan,Brodnik ?ugelj, Helena,?tefane, Bogdan,Kos, Janko,Gobec, Stanislav

supporting information, p. 1239 - 1247 (2018/03/05)

Human cathepsin B is a cysteine protease with many house-keeping functions, such as intracellular proteolysis within lysosomes. Its increased activity and expression have been strongly associated with many pathological processes, including cancers. We present here the design and synthesis of novel derivatives of nitroxoline as inhibitors of cathepsin B. These were prepared either by omitting the pyridine part, or by modifying positions 2, 7, and 8 of nitroxoline. All compounds were evaluated for their ability to inhibit endopeptidase and exopeptidase activities of cathepsin B. For the most promising inhibitors, the ability to reduce extracellular and intracellular collagen IV degradation was determined, followed by their evaluation in cell-based in vitro models of tumor invasion. The presented data show that we have further defined the structural requirements for cathepsin B inhibition by nitroxoline derivatives and provided additional knowledge that could lead to non-peptidic compounds with usefulness against tumor progression.

Rare earth fluorescent material Eu(5-nsa)3(phen) complex and preparation method thereof

-

Paragraph 0012; 0013, (2018/11/03)

The invention provides ternary rare earth complex fluorescent material Eu(5-nsa)3(phen).3H2O (5-nsa is 5-nitrosalicylic acid, phen is o-phenanthroline) and a preparation method thereof, and belongs tothe technical field of fluorescent materials. The preparation method is characterized in that the 5-nitrosalicylic acid is synthesized from salicylic acid as a raw material and acetone as a solvent,and the ternary rare earth complex is synthesized by adding a second ligand (o-phenanthroline) and a rare earth metal ion (Eu) into the 5-nitrosalicylic acid, with a molecular formula being Eu(C7H4O5N)3(C12H8N2).3H2O. The obtained complex, a new rare earth luminescent material, has three fluorescence emission peaks at 463 nm, 602 nm and 623 nm, respectively, under the maximum excitation wavelengthof 400 nm. The luminescence mode of the complex is the integrated luminescence of ligands and rare earth ions. The preparation method is simple in preparation process, simple and convenient in operation and good in product fluorescence characteristics.

A US salad qin industrial preparation method (by machine translation)

-

Paragraph 0015; 0018, (2018/03/24)

The invention discloses a US salad qin industrial preparation method, characterized in that the preparation method is as follows: 1) to 2 - chloro - 5 - nitro-benzoic acid (I) as the starting material, the addition of a base, in a certain temperature lower substitution reaction to produce 2 - hydroxy - 5 - nitro-benzoic acid (intermediate II); 2) a certain pressure and temperature, and the catalyst, under alkaline conditions, for the finished product to the United States of Raney nickel reduction of nitro salad qin. The process of the invention the synthesis cost is low, mild reaction conditions, the whole process uses water as solvent, without the use of toxic reagent, catalyst recycled, the whole process of the green production; the product obtained by the process for high yield, with better purity. (by machine translation)

A 5 - nitro salicylic acid synthesis method (by machine translation)

-

Paragraph 0016; 0017; 0018; 0019, (2017/12/30)

The invention belongs to the field of fine chemicals, in particular to a micro-reactor in order to continuous process of synthesizing 5 - nitro salicylic acid, which is characterized in that the two unit feeding mode, the pump segment and the substrate into the micro-reactor and nitration, the reaction temperature is controlled 55 - 75 °C, the residence time in the reactor 20 - 40 the s, and the resulting reaction mixture rapidly into the countercurrent extraction equipment, continuous liquid aqueous phase and organic phase are collected; the nitrating agent is sulfuric acid, nitric acid mixture, sulfuric acid and nitric acid mole ratio 3 - 4; the substrate is the nitration of salicylic acid and organic solvent solution; said reaction in the nitric acid salicylic acid molar ratio of 1.1 - 1.3. The reaction time of this invention greatly short the prior art 3 hours, using a continuous synthetic method, with the prior intermittent kettle drops compared with the processing technology, more accurate instantaneous matching of materials, reaction is stable, the operation is convenient. (by machine translation)

Novel substituted sulfamide compound, preparation method and application thereof as PTP1B inhibitor

-

Paragraph 0019; 0023, (2017/06/28)

The invention relates to a novel substituted sulfamide compound of a structure of a formula I as shown in the description, a pharmaceutically acceptable salt of the novel substituted sulfamide compound, a preparation method, and relates to a medicinal composition comprising the compound of the formula I or a pharmaceutically acceptable salt of the compound. The compound of the formula I or the pharmaceutically acceptable salt of the compound has activity of inhibiting protein tyrosine phosphatase 1B (PTP1B), so that the compound or the pharmaceutically acceptable salt of the compound has an application of preparing a medicine for preventing/treating symptoms or diseases such as hyperglycemia and type-2 diabetes.

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