53967-72-9

Basic information

• Product Name: 3'-Hydroxy-2'-nitroacetophenone
• Synonyms: 3'-Hydroxy-2'-nitroacetophenone
• CAS NO: 53967-72-9
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181
• Product Categories: Aromatics;Intermediates
• Mol File: 53967-72-9.mol

Chemical Properties

• Melting Point: 134–136°C
• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Dichloromethane
• CAS DataBase Reference: 3'-Hydroxy-2'-nitroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Hydroxy-2'-nitroacetophenone(53967-72-9)
• EPA Substance Registry System: 3'-Hydroxy-2'-nitroacetophenone(53967-72-9)

Safety Data

• Hazardous Substances Data: 53967-72-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3'-Hydroxy-2'-nitroacetophenone is used as a synthetic intermediate for the production of a wide range of organic compounds. Its unique structure, featuring a hydroxyl group and a nitro group on the aromatic ring, allows for versatile chemical reactions and modifications, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, 3'-Hydroxy-2'-nitroacetophenone is utilized as a key component in the development of new drugs. Its chemical properties enable it to be transformed into various drug candidates with potential therapeutic applications, contributing to the advancement of novel treatments for various diseases and medical conditions.
Used in Dye and Pigment Industry:
3'-Hydroxy-2'-nitroacetophenone also finds application in the dye and pigment industry, where it is employed as a starting material for the synthesis of various colorants. Its ability to undergo a range of chemical reactions allows for the creation of dyes and pigments with specific color properties, catering to the diverse needs of this industry.
Used in Chemical Research:
In the realm of chemical research, 3'-Hydroxy-2'-nitroacetophenone serves as an important compound for studying various reaction mechanisms and exploring new synthetic routes. Its unique structure and reactivity make it an attractive candidate for research aimed at understanding and expanding the boundaries of organic chemistry.

Preparation

Obtained by nitration of 3-hydroxyacetophenone with cupric nitrate in acetic acid–acetic anhydride mixture, at 10–15° for 7–8 h (25%).

Upstream product

• 121-71-1 3-Hydroxyacetophenone 
• 33852-43-6 1-(3-methoxy-2-nitrophenyl)ethanone 
• 15865-57-3 2-nitro-3-methoxybenzoyl chloride 

Downstream Products

• 4502-10-7 2'-amino-3'-hydroxyacetophenone 
• 93367-77-2 (E)-4-(3-hydroxy-2-nitrophenyl)-4-oxobut-2-enoic acid 
• 107916-70-1 6,2'-Dinitro-3,3'-dihydroxy-chalkon 
• 199985-13-2 methyl 2-methoxy-2-(3-acetyl-2-nitrophenoxy)acetate 
• 199985-06-3 methyl (3-acetyl-2-nitrophenoxy)acetate 
• 33852-43-6 1-(3-methoxy-2-nitrophenyl)ethanone 
• 102022-92-4 4-(3-benzyloxy-2-nitro-phenyl)-2,4-dioxo-butyric acid ethyl ester 
• 199985-20-1 [2-Nitro-3-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-phenoxy]-acetic acid methyl ester 
• 70735-79-4 4-acetylbenzoxazdin-2(3H)-one 
• 864816-22-8 2-N-[2-isopropoxy-6-({4-(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)ethyl]-1H-pyrrol-3-yl}carbonyl)phenyl]-2-methoxy-3-(4-methoxyphenyl)-2-propenamide 
• 864816-23-9 7-isopropoxy-2-[methoxy-2-(4-methoxyphenyl)ethenyl]-3-{4-(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)ethyl]-1H-pyrrol-3-yl}-1H-indole 
• 864816-19-3 (3-isopropoxy-2-nitrophenyl)-{4-(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)ethyl]-1H-pyrrol-3-yl}methanone 
• 864816-20-6 (2-amino-3-isopropoxyphenyl)-{4-(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)ethyl]-1H-pyrrol-3-yl}methanone 
• 864816-18-2 (2E)-3-isopropoxy-2-nitrophenyl-3-(4-methoxyphenyl)-2-propenone 

Relevant articles and documents

3-Hydroxy-2,6-dinitroacetophenone: an Unusual Substitution Pattern Resulting from Nitration of 3-Hydroxyacetophenone

Nitration of 3-hydroxyacetophenone gives 2,6-dinitro-3-hydroxyacetophenone, C8H6N2O6, in which the nitro groups have entered the sterically least favourable positions in the aromatic nucleus.None of the expected substitution in the 4-position was observed.The two nitro groups flanking the carbonyl side chain are different in that one is in the plane of the aryl ring but the other is twisted well out of the plane.

Study of Anopheles gambiae 3-hydroxykynurenine transaminase activity and inhibition by LC-MS/MS method

In Anopheles gambiae, the most efficient vector of the malaria parasite Plasmodium falciparum, 3-hydroxykynurenine is endowed with a toxic potential. In adult mosquitoes, the excess of 3-hydroxykynurenine is removed by a specific transaminase (3-hydroxyky

Topoisomerase I-mediated antiproliferative activity of 10-substituted and 12-substituted homocamptothecins

Homocamptothecin (hCPT) is an E-ring modified camptothecin (CPT) analogue, which showed pronounced inhibitory activity of topoisomerase I. In search of novel hCPT-type anticancer agents, two series of hCPT derivatives were synthesized and evaluated in vitro against three human tumor cell lines. The results indicated that the 10-substituted hCPT derivatives had a considerably higher cytotoxic activity than the 12-substituted ones. Among the 10-substituted compounds, 8a, 8b, 9b, and 9i showed an equivalent or even more potent activity than the positive control drug topotecan against the lung cancer cell line A-549. Moreover, the hCPT analogues 8a and 8b exhibited a higher topoisomerase I inhibitory activity than CPT at a concentration of 100 μM. Copyright

Synthesis and pharmacological activity of 1,3,6-trisubstituted-4-oxo-1,4- dihydroquinoline-2-carboxylic acids as selective ETA antagonists

A series of 1,3,6-trisubsituted-4-oxo-1,4-dihyroquinoline-2-carboxylic acid analogs (2a-m) were designed and synthesized and their pharmacological activity determined, with the objective to better understand their SAR as potential ETA selective inhibitors. Most of the compounds displayed significant ETA antagonist activity having IC50 for inhibition of binding of the [125I]ET-1 to ETA receptor A antagonism over ETB receptor. Based on the in vitro results, SAR of this series of compounds requires an alkoxy substituent at the 6-position to be a straight and saturated chain up to three carbons long, since substitution of unsaturated and branched alkyloxy groups results in decrease in ETA antagonist activity. In this series, compound 2c (6-O-n-propyl analog) was found to be most potent (IC 50 = 0.11 nM) with ETB/ETA selectivity of 8303.

Novel human lens metabolites from normal and cataractous human lenses

4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human

Total syntheses of the telomerase inhibitors dictyodendrin B, C, and E

Concise and flexible total syntheses of the pyrrolo[2,3-c]carbazole alkaloids dictyodendrin B (2), C (3), and E (5) are described. These polycyclic telomerase inhibitors of marine origin derive from the common intermediate 18 which was prepared on a multigram scale by a sequence comprising a TosMIC cycloaddition with formation of the pyrrole A-ring, a titanium-induced reductive oxoamide coupling reaction to generate an adjacent indole nucleus, and a photochemical 6π-electrocyclization/aromatization tandem to forge the pyrrolocarbazole core. Conversion of 18 into dictyodendrin C required selective manipulations of the lateral protecting groups and oxidation with peroxoimidic acid to form the vinylogous benzoquinone core of the target. Zinc-induced reductive cleavage of the trichloroethyl sulfate ester then completed the first total synthesis of 3. Its relatives 2 and 5 also originate from compound 18 by a selective bromination of the pyrrole entity followed by elaboration of the resulting bromide 27 via metal-halogen exchange or cross-coupling chemistry, respectively. Particularly noteworthy in this context is the generation of the very labile p-quinomethide motif of dictyodendrin E by a palladium-catalyzed benzyl cross-coupling reaction followed by vinylogous oxidation of the resulting product 41 with DDQ. The Suzuki step could only be achieved with the aid of the borate complex 40 formed in situ from p-methoxybenzylmagnesium chloride and 9-MeO-9-BBN, whereas alternative methods employing benzylic boronates, -trifluoroborates, or -stannanes met with failure.

Total synthesis of dictyodendrin B

A concise total synthesis of dictyodendrin B (1) is reported, a scarce marine alkaloid endowed with promising telomerase inhibitory activity. Key steps of the chosen route are a reductive cyclization of ketoamide 11 to indole 12 mediated by low-valent titanium (from TiCl3 and KC8) followed by a photochemical 6π-electrocyclization, which was performed in the presence of Pd/C and nitrobenzene to effect concomitant dehydrogenation/aromatization of the product initially formed. Regioselective bromination of the resulting pyrrolocarbazole 13 followed by lithium/bromine exchange and quenching of the resulting organolithium species with p-methoxybenzaldehyde installed the side chain at C2. Oxidation of the benzylic alcohol 15 thus obtained to ketone 17 was best achieved with catalytic amounts of tetra-n-propylammonium perruthenate (TPAP) and N-methylmorpholine-N-oxide (NMO) in dilute CH2Cl2 solution to avoid the formation of undue amounts of the unsymmetrical dimer 16. Ketone 17 was elaborated into the natural product by selective cleavage of the isopropyl ether with BCl3, introduction of the sulfate moiety with the aid of trichloroethyl chlorosulfuric acid ester, deprotection of all lateral methyl ether groups, and final reductive cleavage of the trichloroethyl ester moiety. The spectroscopic data of synthetic dictyodendrin B thus formed matched those of an authentic sample in all regards. Moreover, it was shown that global deprotection of the peripheral -OH groups in pyrrolo[2,3-c]carbazole 13 is accompanied by spontaneous air-oxidation to form the quinone core of dictyodendrin C. Copyright

Design, synthesis, photochemical properties and cytotoxic activities of water-Soluble caged L-Leucyl-L-leucine methyl esters that control apoptosis of immune cells

L-Leucyl-L-leucine methyl esters (LeuLeuOMe) is a lysosomotropic agent that induces apoptosis of certain immune cells. Glucose-carrying 2-nitrobenzyl (2-NB) and 2-nitrophenethyl (2-NPE) caged LeuLeuOMe, 1a and b, were synthesized and their photochemical a

Synthesis of 4-acetylbenzoxazolin-2(3H)-one reported from Zea mays

A three-step alternative synthesis of 4-acetylbenzoxazolin-2(3H)-one (4) is reported. Starting from inexpensive 3-hydroxyacetophenone (1) 3-hydroxy- 2-nitroacetophenone (2) is prepared by nitration followed by catalytic hydrogenation to yield 2-amino-3-hydroxyacetophenone (3) in which a C=O unit is inserted by means of bis(trichloromethyl)carbonate (triphosgene) in the presence of triethylamine to afford 4 in 35% overall yield.