14543-43-2

Basic information

• Product Name: 2-AMINO-4-CYANO-PHENOL
• Synonyms: 2-AMINO-4-CYANO-PHENOL;3-Amino-4-hydroxybenzonitrile;5-Cyano-2-hydroxyaniline, 2-Amino-5-cyanophenol;2-Amino-5-cyano-phenol;3-amino-4-hydroxybenzonitrile(SALTDATA: FREE);5-Cyano-2-hydroxyaniline, 2-Amino-4-cyanophenol;5-Cyano-2-hydroxy-aniline
• CAS NO: 14543-43-2
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.14
• Product Categories: Amines;Phenyls & Phenyl-Het
• Mol File: 14543-43-2.mol
• Article Data: 29

Chemical Properties

• Melting Point: 151-153℃
• Boiling Point: 345.1 °C at 760 mmHg
• Flash Point: 162.5 °C
• Appearance: /
• Density: 1.33 g/cm³
• Vapor Pressure: 3.15E-05mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.63±0.18(Predicted)
• Sensitive: Air Sensitive
• Stability: Air Sensitive, Light Sensitive
• CAS DataBase Reference: 2-AMINO-4-CYANO-PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-CYANO-PHENOL(14543-43-2)
• EPA Substance Registry System: 2-AMINO-4-CYANO-PHENOL(14543-43-2)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 14543-43-2(Hazardous Substances Data)

Usage

General Description

2-Amino-4-cyano-phenol is a chemical compound with the molecular formula C7H6N2O. It is a phenolic compound with a cyano group and an amino group attached to the benzene ring. 2-Amino-4-cyano-phenol is commonly used as an intermediate in the synthesis of various pharmaceuticals, dyes, and other organic compounds. It has also been studied for its potential antioxidant and antimicrobial properties. The compound may have potential applications in various industrial and medicinal fields due to its unique chemical structure and properties.

InChI:InChI=1/C7H6N2O/c8-4-5-1-2-7(10)6(9)3-5/h1-3,10H,9H2

Upstream product

• 3272-08-0 4-hydroxy-3-nitrobenzonitrile 
• 16237-96-0 4-(Isopropylideneaminoxy)benzonitrile 
• 767-00-0 4-cyanophenol 
• 111318-35-5 4-acetoxy-3-nitro-benzonitrile 

Downstream Products

• 84435-42-7 2-amino-4-amidiniumphenolate dihydrate 
• 93794-41-3 2-mercaptobenzo[d]oxazole-5-carbonitrile 
• 93794-41-3 5-cyanobenzo[d]oxazole-2-(3H)-thiazone 
• 1026273-07-3 2-Bromo-N-(5-cyano-2-hydroxy-phenyl)-acetamide 
• 357156-63-9 N-(5-cyano-2-hydroxy-phenyl)-4-phenoxy-benzamide 
• 357156-65-1 3,5-di-tert-butyl-N-(5-cyano-2-hydroxy-phenyl)-2-hydroxy-benzamide 
• 134997-74-3 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonitrile 
• 357156-64-0 2-(4-phenoxy-phenyl)-benzooxazole-5-carbonitrile 
• 357156-66-2 2-(3,5-di-tert-butyl-2-hydroxy-phenyl)-benzooxazole-5-carbonitrile 
• 114997-92-1 2-chloro-5-cyanobenzo[d]oxazole 
• 875851-64-2 2-(4-cyano-phenyl)-benzoxazole-5-carbonitrile 
• 461699-30-9 N₂-(4-bromophenyl)-5-cyano-1,3-benzoxazol-2-amine 
• 476303-97-6 4-hydroxy-3-{3-[4-(pyrrolidin-1-yl-carbonyl)-3-methyl-phenyl]-propargylamino}-benzonitrile 
• 182498-91-5 N-[2-hydroxy-5-cyanophenyl]-N'-[2-bromophenyl] urea 

Relevant articles and documents

Targeting the subpocket in xanthine oxidase: Design, synthesis, and biological evaluation of 2-[4-alkoxy-3-(1H-tetrazol-1-yl) phenyl]-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid derivatives

Xanthine oxidase is an important target for the treatment of hyperuricemia, gout and other related diseases. Analysis of the high-resolution structure of xanthine oxidase with febuxostat identified the existence of a subpocket formed by the residues Leu648, Asn768, Lys771, Leu1014 and Pro1076. In this study, we designed and synthesized a series of 2-[4-alkoxy-3-(1H-tetrazol-1-yl) phenyl]-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid derivatives (8a-8z) with a tetrazole group targeting this subpocket of the xanthine oxidase active site, and they were further evaluated for their inhibitory potency against xanthine oxidase in vitro. The results showed that all the tested compounds (8a-8z) exhibited an apparent xanthine oxidase inhibitory potency, with IC50 values ranging from 0.0288 μM to 0.629 μM. Among them, compound 8u emerged as the most potent xanthine oxidase inhibitor, with an IC50 value of 0.0288 μM, which was comparable to febuxostat (IC50 = 0.0236 μM). The structure-activity relationship results revealed that the hydrophobic group at the 4′-position was indispensable for the inhibitory potency in vitro against xanthine oxidase. A Lineweaver-Burk plot revealed that the representative compound 8u acted as a mixed-type inhibitor for xanthine oxidase. Furthermore, molecular modeling studies were performed to gain insights into the binding mode of 8u with xanthine oxidase and suggested that the tetrazole group of the phenyl unit was accommodated in the subpocket, as expected. Moreover, a potassium oxonate-induced hyperuricemia model in rats was chosen to further confirm the hypouricemic effect of compound 8u, and the result demonstrated that compound 8u could effectively reduce serum uric acid levels at an oral dose of 5 mg/kg. In addition, acute oral toxicity study in mice indicated that compound 8u was nontoxic and tolerated at a dose up to 2000 mg/kg. Thus, compound 8u could be a potential and efficacious agent in treatment of hyperuricemia with low toxicity.

Phenazine and phenothiazine covalent triazine framework material as well as preparation method and application thereof

The invention discloses a phenazine or phenothiazine covalent triazine framework material and a preparation method and application thereof. After the reaction is finished, water and acid are used for washing, and the obtained solid product is a phenazine

Compounds with xanthine oxidase inhibition activity, and preparation method and application thereof

The invention belongs to the technical field of medicines, and relates to compounds with xanthine oxidase inhibition activity, and a preparation method and an application thereof. The invention provides the compounds with xanthine oxidase inhibition activity, represented by general formula I, or pharmaceutically acceptable salts, isomers, polymorphs and medical solvates thereof, and further provides an intermediate for preparing the compounds with xanthine oxidase inhibition activity, or the pharmaceutically acceptable salts thereof. The structure of the intermediate is represented by generalformula II or III shown in the description; and R in the general formulas is as defined in claims and the description.