3272-08-0

Basic information

• Product Name: 4-Hydroxy-3-nitrobenzonitrile
• Synonyms: 4-CYANO-2-NITROPHENOL;4-HYDROXY-3-NITROBENZONITRILE;2-NITRO-4-CYANOPHENOL;4-HYDROXY-3-NITROBENZONITRILE / 2-NITRO-4-CYANOPHENOL;4-HYDROXY-3-NITROBENZONITRILE 97%;4-BROMO-2,6-DIETHOXY-1-NITROBENZENE;Benzonitrile, 4-hydroxy-3-nitro-;3-Nitro-4-hydroxybenzonitrile
• CAS NO: 3272-08-0
• Molecular Formula: C₇H₄N₂O₃
• Molecular Weight: 164.12
• EINECS: 221-899-8
• Product Categories: Aromatic Nitriles;Phenoles and thiophenoles;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Aromatic Building Blocks;Building Blocks;C6 to C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 3272-08-0.mol

Chemical Properties

• Melting Point: 146-148 °C(lit.)
• Boiling Point: 291.56°C (rough estimate)
• Flash Point: 128.5 °C
• Appearance: yellow solid powder
• Density: 1.5018 (rough estimate)
• Vapor Pressure: 0.00131mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.66±0.14(Predicted)
• CAS DataBase Reference: 4-Hydroxy-3-nitrobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-3-nitrobenzonitrile(3272-08-0)
• EPA Substance Registry System: 4-Hydroxy-3-nitrobenzonitrile(3272-08-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36/37/39-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3272-08-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Hydroxy-3-nitrobenzonitrile is used as a synthetic intermediate for the production of various compounds, such as 3-azido-4-methoxybenzonitrile and 4-methoxy-3-nitrobenzonitrile. These synthesized compounds can be utilized in different applications, including pharmaceuticals and other chemical industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Hydroxy-3-nitrobenzonitrile is used as a key intermediate in the synthesis of ethyl [2,2-dimethyl-6-(Δ2-thiazolin-2-yl)-4H-1,4-benzoxazin-3-one-4-yl] butyrate. 4-Hydroxy-3-nitrobenzonitrile has potential applications in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
4-Hydroxy-3-nitrobenzonitrile plays a role in the degradation of herbicides, specifically bromoxynil. Understanding the formation and properties of this compound can help in the development of more effective and environmentally friendly herbicides, as well as in the improvement of existing ones.

InChI:InChI=1/C7H4N2O3/c8-4-5-1-2-7(10)6(3-5)9(11)12/h1-3,10H/p-1

Upstream product

• 110-89-4 piperidine 
• 23886-19-3 3,3'-dinitro-4,4'-oxy-di-benzonitrile 
• 89642-49-9 4-bromo-3-nitrobenzonitrile 
• 111318-35-5 4-acetoxy-3-nitro-benzonitrile 
• 767-00-0 4-cyanophenol 
• 939-80-0 4-chloro-3-nitrobenzonitrile 
• 60-35-5 acetamide 
• 7732-18-5 water 
• 127-09-3 sodium acetate 
• 7664-93-9 sulfuric acid 
• 57928-64-0 4-phenethyloxybenzonitrile 
• 7697-37-2 nitric acid 
• 6508-04-9 4-(4'-cyanophenoxy)benzonitrile 
• 3011-34-5 4-hydroxy-3-nitrobenzaldehyde 

Downstream Products

• 16588-23-1 3-nitro-4-(phenylamino)benzonitrile 
• 939-80-0 4-chloro-3-nitrobenzonitrile 
• 1689-89-0 nitroxynil 
• 33224-23-6 4-Cyano-2-nitroanisol 
• 1026637-70-6 3-nitro-4-(3-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-prop-2-ynyloxy)-benzonitrile 
• 134997-74-3 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonitrile 
• 1026273-07-3 2-Bromo-N-(5-cyano-2-hydroxy-phenyl)-acetamide 
• 114997-92-1 2-chloro-5-cyanobenzo[d]oxazole 
• 93794-41-3 5-cyanobenzo[d]oxazole-2-(3H)-thiazone 
• 1828-58-6 3-bromo-4-hydroxy-5-nitrobenzonitrile 
• 652997-70-1 methyl (4-cyano-2-nitrophenoxy)acetate 
• 105450-74-6 4-hydroxy-3-nitro-benzamidine hydrochloride 

Relevant articles and documents

Facile entry into structurally diverse, privileged, (hetero)arene-fused N-alkoxy 3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ones

Rare and highly medicinally relevant N-alkoxy-substituted benzo[1,4]oxazepines have been synthesized conveniently via the base-promoted SNAr/Smiles rearrangement/SNAr tandem cyclization of N-alkoxysalicylamides with a range of bis-electrophilic substrates; subsequent de-alkylation gives rise to the respective N-hydroxy versions. The compounds reported herein significantly add to the contemporary arsenal of small molecule tools for drug discovery.

Amidino substituted 2-aminophenols: biologically important building blocks for the amidino-functionalization of 2-substituted benzoxazoles

Unlike the closely related and widely investigated amidino-substituted benzimidazoles and benzothiazoles with a range of demonstrated biological activities, the matching benzoxazole analogues still remain a largely understudied and not systematically evaluated class of compounds. To address this challenge, we utilized the Pinner reaction to convert isomeric cyano-substituted 2-aminophenols into their amidine derivatives, which were isolated as hydrochlorides and/or zwitterions, and whose structure was confirmed by single crystal X-ray diffraction. The key step during the Pinner synthesis of the crucial carboximidate intermediates was characterized through mechanistic DFT calculations, with the obtained kinetic and thermodynamic parameters indicating full agreement with the experimental observations. The obtained amidines were subjected to a condensation reaction with aryl carboxylic acids that allowed the synthesis of a new library of 5- and 6-amidino substituted 2-arylbenzoxazoles. Their antiproliferative features against four human tumour cell lines (SW620, HepG2, CFPAC-1, HeLa) revealed sub-micromolar activities on SW620 for several cyclic amidino 2-naphthyl benzoxazoles, thus demonstrating the usefulness of the proposed synthetic strategy and promoting amidino substituted 2-aminophenols as important building blocks towards biologically active systems.

Novel pleconaril derivatives: Influence of substituents in the isoxazole and phenyl rings on the antiviral activity against enteroviruses

Today, there are no medicines to treat enterovirus and rhinovirus infections. In the present study, a series of novel pleconaril derivatives with substitutions in the isoxazole and phenyl rings was synthesized and evaluated for their antiviral activity against a panel of pleconaril-sensitive and -resistant enteroviruses. Studies of the structure-activity relationship demonstrate the crucial role of the N,N-dimethylcarbamoyl group in the isoxazole ring for antiviral activity against pleconaril-resistant viruses. In addition, one or two substituents in the phenyl ring directly impact on the spectrum of antienteroviral activity. The 3-(3-methyl-4-(3-(3-N,N-dimethylcarbamoyl-isoxazol-5-yl)propoxy)phenyl)-5-trifluoromethyl-1,2,4-oxadiazole 10g was among the compounds exhibiting the strongest activity against pleconaril-resistant as well as pleconaril-susceptible enteroviruses with IC50 values from 0.02 to 5.25 μM in this series. Compound 10g demonstrated markedly less CYP3A4 induction than pleconaril, was non-mutagenic, and was bioavailable after intragastric administration in mice. These results highlight compound 10g as a promising potential candidate as a broad spectrum enterovirus and rhinovirus inhibitor for further preclinical investigations.

Tetrazole xanthine oxidase inhibitor compound as well as preparation method and application thereof

The invention belongs to the technical field of medicines and relates to a tetrazole xanthine oxidase inhibitor compound as well as a preparation method and application thereof. The invention providesa tetrazole xanthine oxidase inhibitor compound shown as a general formula I or a pharmaceutically acceptable salt, an isomer, a polymorphic substance and a medicinal solvate and further provides anintermediate for preparing the tetrazole xanthine oxidase inhibitor compound or the pharmaceutically acceptable salt, and a structure of the intermediate is shown as a general formula II, III or IV, wherein R is described as claims and a description.

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.

Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation

The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.

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.

ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

METHOD FOR PREPARING AFATINIB AND INTERMEDIATE THEREOF

Revealed in the present invention is a method for preparing Afatinib (I): using 2-nitrile-4-[4-(N,N-dimethylamino)-I-oxo-2-buten-I-yl]amino-5-[(S)-(tetrahydrofuran-3-yl)oxy]aniline (II) and 4-fluoro-3-chloroaniline (III) as starting materials, and respectively performing a condensation and cyclization reaction with N,N-dimethylformamide dimethyl acetal (IV) to prepare Afatinib (I), wherein the method significantly reduces the manufacturing steps of Afatinib and greatly lower the costs. In addition, also provided in the present invention is a method for preparing an intermediate of Afatinib, wherein the method has a stable process, uses readily available starting materials, has a low cost, and all the reactions are classic reactions, suitable for meeting amplification requirements in the industry.

Improved schmidt conversion of aldehydes to nitriles using azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-Propanol

The Schmidt reaction of aromatic aldehydes using a substoichiometric amount (40 mol %) of triflic acid is described. Low catalyst loading was enabled by a strong hydrogen-bond-donating solvent hexafluoro-2-propanol (HFIP). This improved protocol tolerates a broad scope of aldehydes with diverse functional groups and the corresponding nitriles were obtained in good to high yields without the need for aqueous work up.