28123-73-1

Basic information

• Product Name: 5-(4-NITROPHENYL)-2-FUROIC ACID
• Synonyms: ASISCHEM T31195;ART-CHEM-BB B025354;AKOS BB-8339;5-(4-NITROPHENYL)-2-FURANCARBOXYLIC ACID;5-(4-NITROPHENYL)-2-FUROIC ACID;5-(4-NITRO-PHENYL)-FURAN-2-CARBOXYLIC ACID;RARECHEM AL BE 0741;5-(4-Nitrophenyl)-furane-2-carboxylic acid
• CAS NO: 28123-73-1
• Molecular Formula: C₁₁H₇NO₅
• Molecular Weight: 233.18
• Product Categories: API intermediates
• Mol File: 28123-73-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 255-257 °C (dec.)(lit.)
• Boiling Point: 451.4°Cat760mmHg
• Flash Point: 226.8°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 6.16E-09mmHg at 25°C
• CAS DataBase Reference: 5-(4-NITROPHENYL)-2-FUROIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-NITROPHENYL)-2-FUROIC ACID(28123-73-1)
• EPA Substance Registry System: 5-(4-NITROPHENYL)-2-FUROIC ACID(28123-73-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 28123-73-1(Hazardous Substances Data)

Usage

Description

5-(4-NITROPHENYL)-2-FUROIC ACID, also known as 5-(p-nitrophenyl)-2-furoic acid, is a 5-aryl-2-furoic acid derivative. It is a metabolite of dantrolene, a drug used to treat certain muscle spasm conditions. The presence of this compound in plasma and urine can be determined by high-performance liquid chromatography (HPLC). It is formed as the sole product during the reduction of 5-(4-nitrophenyl)-2-furaldehyde through a modified Cannizzaro reaction.

Uses

1. Used in Pharmaceutical Research:
5-(4-NITROPHENYL)-2-FUROIC ACID is used as a research compound for studying its metabolic pathways and interactions with other molecules. Its identification in biological samples helps in understanding the metabolism of dantrolene and its potential effects on muscle spasm conditions.
2. Used in Analytical Chemistry:
In the field of analytical chemistry, 5-(4-NITROPHENYL)-2-FUROIC ACID is used as a reference compound for the development and validation of HPLC methods. Its detection and quantification in plasma and urine samples contribute to the assessment of dantrolene's pharmacokinetics and pharmacodynamics.
3. Used in Drug Metabolism Studies:
5-(4-NITROPHENYL)-2-FUROIC ACID is used as a metabolite of interest in drug metabolism studies. Researchers can investigate the enzymes and pathways involved in the conversion of dantrolene to this metabolite, which may provide insights into the drug's mechanism of action and potential side effects.
4. Used in Toxicology:
In toxicology, 5-(4-NITROPHENYL)-2-FUROIC ACID can be used to study the potential toxic effects of dantrolene and its metabolites. Understanding the toxicokinetics and toxicodynamics of this compound can help in the development of safer and more effective treatments for muscle spasm conditions.
5. Used in Quality Control:
5-(4-NITROPHENYL)-2-FUROIC ACID is used as a quality control standard in the pharmaceutical industry. It can be employed to ensure the accuracy and reliability of analytical methods used in the production and testing of dantrolene and its formulations.

InChI:InChI=1/C11H7NO5/c13-11(14)10-6-5-9(17-10)7-1-3-8(4-2-7)12(15)16/h1-6H,(H,13,14)/p-1

Upstream product

• 98-01-1 furfural 
• 88-14-2 2-furanoic acid 
• 100-01-6 4-nitro-aniline 
• 52939-00-1 5-(4-nitrophenyl)furan-2-carboxylic acid methyl ester 
• 2527-99-3 methyl 5-bromo-2-furoate 
• 24067-17-2 4-nitrophenylboronic acid 
• 7147-77-5 5-(4-nitrophenyl)-2-furaldehyde 

Downstream Products

• 226710-79-8 tert-butyl N-<2-(5-p-nitrophenylfuryl)>carbamate 
• 92973-03-0 {[1-Chloro-1-[5-(4-nitro-phenyl)-furan-2-yl]-meth-(Z)-ylidene]-amino}-acetic acid ethyl ester 
• 92972-92-4 {[5-(4-Nitro-phenyl)-furan-2-carbonyl]-amino}-acetic acid ethyl ester 
• 92972-84-4 {5-[5-(4-Nitro-phenyl)-furan-2-yl]-tetrazol-1-yl}-acetic acid 
• 92972-79-7 {5-[5-(4-Nitro-phenyl)-furan-2-yl]-tetrazol-1-yl}-acetic acid ethyl ester 
• 69333-30-8 1-methyl-4-piperidyl 5-(p-nitrophenyl)-2-furoate hydrochloride 
• 1144110-87-1 C₂₁H₁₅N₅O₃S₂ 
• 851909-45-0 (+/-) 5-(4-nitro-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide 
• 869347-90-0 (+/-) 5-(4-amino-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide 

Relevant articles and documents

Carbon–Carbon Bond Formation for the Synthesis of 5-Aryl-2-Substituted Furans Catalyzed by K3[Fe(CN)6]

An efficient method for the carbon–carbon bond formation at C-5 position of 2-substituted furans to provide a range of π-diverse 5-aryl-2-substituted furan derivatives in 58–80% yield has been reported. The method employs several advantages such as use of catalytic amount of K3[Fe(CN)6] under mild conditions and short reaction time with high yields. Also, a variety of anilines with a variety of functional groups can be employed for the synthesis of 5-aryl-2-substituted furans. Graphic Abstract: [Figure not available: see fulltext.]

Thiazolidin-2-cyanamides derivatives as novel potent Escherichia coli β-glucuronidase inhibitors and their structure–inhibitory activity relationships

Gut microbial β-glucuronidases have the ability to deconjugate glucuronides of some drugs, thus have been considered as an important drug target to alleviate the drug metabolites-induced gastrointestinal toxicity. In this study, thiazolidin-2-cyanamide de

Synthesis and SAR of 5-aryl-furan-2-carboxamide derivatives as potent urotensin-II receptor antagonists

The synthesis and biological evaluation as potential urotensin-II receptor antagonists of a series of 5-arylfuran-2-carboxamide derivatives 1, bearing a 4-(3-chloro-4-(piperidin-4-yloxy)benzyl)piperazin-1-yl group, are described. The results of a systemat