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

• 93367-77-2 (E)-4-(3-hydroxy-2-nitrophenyl)-4-oxobut-2-enoic acid 
• 199985-10-9 2-(3-hydroxy-2-nitrophenyl)-2,5,5-trimethyl-1,3-dioxane 
• 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 
• 864816-17-1 3-isopropoxy-2-nitrophenylethanone 
• 199985-06-3 methyl (3-acetyl-2-nitrophenoxy)acetate 
• 199985-13-2 methyl 2-methoxy-2-(3-acetyl-2-nitrophenoxy)acetate 

Relevant articles and documents

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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.

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