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METHYL 2-HYDROXY-4-NITROBENZOATE, an organic compound with the chemical formula C8H7NO5, is a yellow crystalline solid that is widely recognized for its anti-inflammatory and analgesic properties. It is commonly utilized in the pharmaceutical and chemical industries, serving as an active ingredient in topical pain relief formulations and as a crucial intermediate in the synthesis of various pharmaceutical drugs and other organic compounds.

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  • 13684-28-1 Structure
  • Basic information

    1. Product Name: METHYL 2-HYDROXY-4-NITROBENZOATE
    2. Synonyms: METHYL 2-HYDROXY-4-NITROBENZOATE;NSC 165605;Methyl 4-Nitrosalicylate
    3. CAS NO:13684-28-1
    4. Molecular Formula: C8H7NO5
    5. Molecular Weight: 197.15
    6. EINECS: N/A
    7. Product Categories: alcohol| carboxylic ester| nitro-compound
    8. Mol File: 13684-28-1.mol
  • Chemical Properties

    1. Melting Point: 101-102 °C
    2. Boiling Point: 324.5 °C at 760 mmHg
    3. Flash Point: 150.1 °C
    4. Appearance: /
    5. Density: 1.432 g/cm3
    6. Vapor Pressure: 0.000129mmHg at 25°C
    7. Refractive Index: 1.59
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. PKA: 8.08±0.19(Predicted)
    11. CAS DataBase Reference: METHYL 2-HYDROXY-4-NITROBENZOATE(CAS DataBase Reference)
    12. NIST Chemistry Reference: METHYL 2-HYDROXY-4-NITROBENZOATE(13684-28-1)
    13. EPA Substance Registry System: METHYL 2-HYDROXY-4-NITROBENZOATE(13684-28-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 13684-28-1(Hazardous Substances Data)

13684-28-1 Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-HYDROXY-4-NITROBENZOATE is used as an active ingredient for its anti-inflammatory and analgesic properties, primarily in the development of topical pain relief creams and ointments. It aids in providing relief from inflammation and pain, making it a valuable component in formulations targeting musculoskeletal and other types of pain.
Used in Chemical Synthesis:
METHYL 2-HYDROXY-4-NITROBENZOATE is used as an important intermediate in the synthesis of various pharmaceutical drugs. Its role in the production of other organic compounds highlights its versatility and significance in the chemical industry.
Safety Precautions:
Due to its potential health hazards, METHYL 2-HYDROXY-4-NITROBENZOATE should be handled and stored with proper safety measures to ensure the well-being of individuals involved in its production, use, and disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 13684-28-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,6,8 and 4 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 13684-28:
(7*1)+(6*3)+(5*6)+(4*8)+(3*4)+(2*2)+(1*8)=111
111 % 10 = 1
So 13684-28-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO5/c1-14-8(11)6-3-2-5(9(12)13)4-7(6)10/h2-4,10H,1H3

13684-28-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 2-hydroxy-4-nitrobenzoate

1.2 Other means of identification

Product number -
Other names 2-Hydroxy-4-nitro-benzoesaeure-methylester

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:13684-28-1 SDS

13684-28-1Relevant articles and documents

Peptidomimetic analogues of an Arg-Trp-x-x-Trp motif responsible for interaction of translocase MraY with bacteriophage ?X174 lysis protein E

Kerr, Rachel V.,Fairbairn, Julia A.,Merritt, Andrew T.,Bugg, Timothy D.H.

, (2021/11/23)

Translocase MraY is the target for bacteriophage ?X174 lysis protein E, which interacts via a protein–protein interaction mediated by Phe-288 and Glu-287 of E. coli MraY, and an Arg-Trp-x-x-Trp motif on protein E, also found in several cationic antimicrob

Cystobactamid 507: Concise Synthesis, Mode of Action, and Optimization toward More Potent Antibiotics

Elgaher, Walid A. M.,Hamed, Mostafa M.,Baumann, Sascha,Herrmann, Jennifer,Siebenbürger, Lorenz,Krull, Jana,Cirnski, Katarina,Kirschning, Andreas,Br?nstrup, Mark,Müller, Rolf,Hartmann, Rolf W.

supporting information, p. 7219 - 7225 (2020/05/08)

Lack of new antibiotics and increasing antimicrobial resistance are among the main concerns of healthcare communities nowadays, and these concerns necessitate the search for novel antibacterial agents. Recently, we discovered the cystobactamids—a novel natural class of antibiotics with broad-spectrum antibacterial activity. In this work, we describe 1) a concise total synthesis of cystobactamid 507, 2) the identification of the bioactive conformation using noncovalently bonded rigid analogues, and 3) the first structure–activity relationship (SAR) study for cystobactamid 507 leading to new analogues with high metabolic stability, superior topoisomerase IIA inhibition, antibacterial activity and, importantly, stability toward the resistant factor AlbD. Deeper insight into the mode of action revealed that the cystobactamids employ DNA minor-groove binding as part of the drug–target interaction without showing significant intercalation. By designing a new analogue of cystobactamid 919-2, we finally demonstrated that these findings could be further exploited to obtain more potent hexapeptides against Gram-negative bacteria.

Discovery of new ATP-competitive inhibitors of human DNA topoisomerase IIα through screening of bacterial topoisomerase inhibitors

Baran?oková, Michaela,Durcik, Martina,Gramec Skledar, Darja,Ila?, Janez,Kikelj, Danijel,Peterlin Ma?i?, Lucija,Skok, ?iga,Toma?i?, Tihomir,Zega, Anamarija,Zidar, Nace

, (2020/07/21)

Human DNA topoisomerase II is one of the major targets in anticancer therapy, however ATP-competitive inhibitors of this target have not yet reached their full potential. ATPase domain of human DNA topoisomerase II belongs to the GHKL ATPase superfamily and shares a very high 3D structural similarity with other superfamily members, including bacterial topoisomerases. In this work we report the discovery of a new chemotype of ATP-competitive inhibitors of human DNA topoisomerase IIα that were discovered through screening of in-house library of ATP-competitive inhibitors of bacterial DNA gyrase and topoisomerase IV. Systematic screening of this library provided us with 20 hit compounds. 1,2,4-Substituted N-phenylpyrrolamides were selected for a further exploration which resulted in 13 new analogues, including 52 with potent activity in relaxation assay (IC50 = 3.2 μM) and ATPase assay (IC50 = 0.43 μM). Cytotoxic activity of all hits was determined in MCF-7 cancer cell line and the most potent compounds, 16 and 20, showed an IC50 value of 8.7 and 8.2 μM, respectively.

2-ARYLSULFONAMIDO-N-ARYLACETAMIDE DERIVATIZED STAT3 INHIBITORS

-

Paragraph 00616; 00729, (2018/08/20)

The present disclosure provides pharmaceutical compositions comprising 2-arylsulfonamido-N-arylacetamide derivatized Stat3 inhibitors and certain pharmaceutically acceptable salts thereof, and methods of their use.

New N-phenylpyrrolamide DNA gyrase B inhibitors: Optimization of efficacy and antibacterial activity

Durcik, Martina,Lovison, Denise,Skok, ?iga,Durante Cruz, Cristina,Tammela, P?ivi,Toma?i?, Tihomir,Benedetto Tiz, Davide,Draskovits, Gábor,Nyerges, ákos,Pál, Csaba,Ila?, Janez,Peterlin Ma?i?, Lucija,Kikelj, Danijel,Zidar, Nace

supporting information, p. 117 - 132 (2018/05/24)

The ATP binding site located on the subunit B of DNA gyrase is an attractive target for the development of new antibacterial agents. In recent decades, several small-molecule inhibitor classes have been discovered but none has so far reached the market. We present here the discovery of a promising new series of N-phenylpyrrolamides with low nanomolar IC50 values against DNA gyrase, and submicromolar IC50 values against topoisomerase IV from Escherichia coli and Staphylococcus aureus. The most potent compound in the series has an IC50 value of 13 nM against E. coli gyrase. Minimum inhibitory concentrations (MICs) against Gram-positive bacteria are in the low micromolar range. The oxadiazolone derivative 11a, with an IC50 value of 85 nM against E. coli DNA gyrase displays the most potent antibacterial activity, with MIC values of 1.56 μM against Enterococcus faecalis, and 3.13 μM against wild type S. aureus, methicillin-resistant S. aureus (MRSA) and vancomycin-resistant Enterococcus (VRE). The activity against wild type E. coli in the presence of efflux pump inhibitor phenylalanine-arginine β-naphthylamide (PAβN) is 4.6 μM.

LANTHANIDE CLUSTERS AND METHODS OF USE THEREOF

-

Paragraph 0212; 0213, (2016/01/30)

The present invention is directed to multinuclear lanthanides chiral clusters, based on phenyl-oxazoline-amide (POxA) ligands, and to methods of use thereof. The chiral clusters of this invention are highly fluorescent with high stability.

1-PHENYL-2-PYRIDINYL ALKYL ALCOHOL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS

-

Paragraph 0432; 0433, (2014/06/23)

Compounds of formula (I) described herein are inhibitors of the phosphodiesterase 4 (PDE4) enzyme and are useful for the prevention and/or treatment of an allergic disease state or a disease of the respiratory tract characterized by airway obstruction.

Discovery and structure-activity relationship of novel 2,3- dihydrobenzofuran-7-carboxamide and 2,3-dihydrobenzofuran-3(2 h)-one-7-carboxamide derivatives as poly(ADP-ribose)polymerase-1 Inhibitors

Patel, Maulik R.,Bhatt, Aaditya,Steffen, Jamin D.,Chergui, Adel,Murai, Junko,Pommier, Yves,Pascal, John M.,Trombetta, Louis D.,Fronczek, Frank R.,Talele, Tanaji T.

, p. 5579 - 5601 (2014/08/05)

Novel substituted 2,3-dihydrobenzofuran-7-carboxamide (DHBF-7-carboxamide) and 2,3-dihydrobenzofuran-3(2H)-one-7-carboxamide (DHBF-3-one-7-carboxamide) derivatives were synthesized and evaluated as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1). A structure-based design strategy resulted in lead compound 3 (DHBF-7-carboxamide; IC50 = 9.45 μM). To facilitate synthetically feasible derivatives, an alternative core was designed, DHBF-3-one-7-carboxamide (36, IC50 = 16.2 μM). The electrophilic 2-position of this scaffold was accessible for extended modifications. Substituted benzylidene derivatives at the 2-position were found to be the most potent, with 3′,4′-dihydroxybenzylidene 58 (IC50 = 0.531 μM) showing a 30-fold improvement in potency. Various heterocycles attached at the 4′-hydroxyl/4′-amino of the benzylidene moiety resulted in significant improvement in inhibition of PARP-1 activity (e.g., compounds 66-68, 70, 72, and 73; IC50 values from 0.718 to 0.079 μM). Compound 66 showed selective cytotoxicity in BRCA2-deficient DT40 cells. Crystal structures of three inhibitors (compounds (-)-13c, 59, and 65) bound to a multidomain PARP-1 structure were obtained, providing insights into further development of these inhibitors.

Specific detection and imaging of enzyme activity by signal-amplifiable self-assembling 19Fa MRI probes

Matsuo, Kazuya,Kamada, Rui,Mizusawa, Keigo,Imai, Hirohiko,Takayama, Yuki,Narazaki, Michiko,Matsuda, Tetsuya,Takaoka, Yousuke,Hamachi, Itaru

supporting information, p. 12875 - 12883 (2013/10/01)

Specific turn-on detection of enzyme activities is of fundamental importance in drug discovery research, as well as medical diagnostics. Although magnetic resonance imaging (MRI) is one of the most powerful techniques for noninvasive visualization of enzy

Bis-TEGylated poly(p-benzamide)s: Combining organosolubility with shape persistence

Schulze, Maren,Michen, Benjamin,Fink, Alke,Kilbinger, Andreas F. M.

, p. 5520 - 5530 (2013/08/23)

The synthesis of perfectly planar, bis-substituted aromatic polyamides is reported herein. With highly flexible triethylene glycol chains attached and conformational restriction through intramolecular, bifurcated hydrogen bonds these are among the most shape-persistent yet organo-soluble polymers to date. Starting from 4-nitrosalicylic acid, our group developed a route to phenyl-2,5-bis-TEGylated aminobenzoate, which could be polymerized by addition of lithium bis(trimethylsilyl)amide (LiHMDS). Since this technique has not been applied to step-growth polycondensations of polyaramides so far, the influence of two different solvents and an N-protective group was investigated. Therefore, substituted phenyl aminobenzoate derivatives carrying a free amine or an N-protective group have been polymerized. Additionally, the tendency for self-assembly of the readily soluble bis-TEGylated poly(p-benzamide) was observed by transmission electron microscopy (TEM) in the dried state. Dynamic light scattering (DLS) measurements of chloroform solutions did not indicate the formation of aggregates. Thus, intermolecular interactions, which other aromatic polyamides typically exhibit, are prevented. The access to bis-substituted, entirely rigid poly(p-benzamide)s via this new polycondensation method paves the way for exciting new structures in materials science and supramolecular chemistry.

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